Process for preparing one or more C-glycoside derivatives comprising a catalytic reduction step

Abstract

The present invention relates to a process for preparing one or more C-glycoside derivatives of formula (I), as described below, preferably of formula (I'), and their optical isomers, geometric isomers, and / or their solvates such as hydrates, comprising at least one purification step carried out in aqueous medium. The invention also relates to a process for preparing one or more C-glycoside derivatives of formula (I1), as described below, comprising a reduction step, carried out in aqueous medium, of at least one compound of formula (I), preferably of formula (I').

Description

Title of the invention: A process for preparing one or more C-glycoside derivatives comprising a catalytic reduction step

[0001] The present invention relates to a process for preparing one or more C-glycoside derivatives corresponding to formula (I), as described below, preferably corresponding to formula (!') or (I”), and their optical isomers, geometric isomers, and / or their solvates such as hydrates, comprising at least one purification step carried out in an aqueous reaction medium.

[0002] The invention also relates to a method for purifying at least one aqueous reaction medium including at least one C-glycoside derivative corresponding to formula (I) and at least one impurity of formula (IV), as described below.

[0003] The processes for synthesizing active, organic and water-soluble ingredients with interesting cosmetic properties can lead to the formation of impurities, in ionic form, which are most often difficult to minimize, or even eliminate, without significantly impacting the yield of the final cosmetic active compound.

[0004] Furthermore, such impurities, when present with the final cosmetic active compound, can generate an undesirable color, texture change, or odor in cosmetic compositions using said active compound. Thus, such impurities can cause a strong, unpleasant odor, for example, a pungent, strongly vinegary smell, which may persist even after several purification steps and prove bothersome and persistent for consumers even after formulation, especially given the current trend toward using fewer and fewer fragrances in cosmetic products to mask or neutralize this type of odor.

[0005] Such impurities can also cause compatibility problems with other additives that may be present in the final cosmetic formulations.

[0006] Such impurities can also be salts of acids or bases that will affect the pH in an aqueous environment. This effect is all the more problematic when the cosmetic active ingredient is isolated as a concentrated aqueous solution.

[0007] Furthermore, the presence of such impurities, particularly inorganic and / or organic salts, can induce a significant increase in the viscosity of the aqueous reaction medium containing the cosmetic active ingredient(s), thus making it difficult, in some cases, to obtain concentrated solutions of cosmetic active ingredients intended for the formulation.

[0008] By way of example, C-glycoside derivatives are water-soluble organic compounds whose properties are generally of interest in the field of cosmetics, particularly in skincare compositions, in order to be used to stimulate the synthesis of glycosaminoglycans present in the dermis and to provide, in particular, density and firmness to the skin (see, for example, the scientific article entitled in English: Synthesis of Pro-XylaneTM: A new bio-logically active C-glycoside in aqueous media, M.Dalko-Csiba et al., Bioorganic & Medicinal Chemistry Letters 19 (2009) 845-849).

[0009] C-glycoside derivatives, such as xylose C-glycoside derivatives, are generally synthesized by means of a reaction, known as the Lubineau reaction (Rodrigues, F., Canac, Y. and Lubineau, A., A convenient, one-step, synthesis of [3-C-glycosidic ketones in aqueous media. - Chemical Communications - 2000, (20), 2049-2050), from an unprotected monosaccharide or polysaccharide, for example D-xylose, and a beta-dicarbonyl compound, for example acetylacetone, in an aqueous medium in the presence of alkaline agent(s).

[0010] The Lubineau reaction is carried out with at least one alkaline agent, such as sodium bicarbonate or soda, present in an equimolar amount or in excess relative to the monosaccharide or polysaccharide, preferably in excess, for a reaction time that may vary from 5 minutes to 20 hours depending on the nature of the alkaline agent and / or the reaction parameters such as concentration and / or temperature.

[0011] However, such a synthesis reaction has the major drawback of leading to the formation of impurities, in particular in the form of salts, for example in the form of organic salt, such as sodium acetate, the residual quantities of which can prove to be significant and difficult to reduce even by implementing several conventional purification and / or washing operations.

[0012] Following this reaction, the aqueous reaction medium can be neutralized with at least one acidifying agent, in particular a mineral, for example hydrochloric acid, to convert the organic acid salt into organic acid, in particular by transforming sodium acetate into acetic acid, and then to reduce the quantities of organic acid to commercially acceptable levels.

[0013] However, neutralization of the reaction medium with at least one mineral acidifying agent, such as hydrochloric acid, also leads to the formation of salts, in particular sodium chloride, which can be removed by precipitation through the addition of water-miscible solvents such as alcohols, in particular isobutanol or ethanol.

[0014] It is known in the prior art to add at the end of the reaction an immiscible solvent to Water is used to wash the aqueous reaction mixture, which is then passed through a pre-conditioned acidic resin before being concentrated in the presence of alcohol. This process involves successive distillations to remove water, followed by the addition of alcohol, which may cause salt crystallization. This may be followed by further washing, possibly with several cycles of water addition, to reduce the salt content to acceptable levels in commercial solutions intended for use in cosmetics.

[0015] Following these various purification operations, the C-glycoside derivatives obtained can be pure without solvent and then, in some cases, undergo a hydrogenation reaction aimed at reducing the ketone function of the C-glycoside derivative and from the beta-dicarbonyl derivative, into a hydroxyl function.

[0016] In particular, C-glycoside derivatives of xylose, such as C-beta-D-xylopyranoside-n-propane-2-one, can further undergo a reduction reaction to lead to C-beta-D-xylopyranoside-2-hydroxy-propane.

[0017] However, such purification operations, including those carried out repeatedly in succession, have not made it possible to satisfactorily reduce the impurities generated during the process of preparing C-glycosides derivatives, particularly on an industrial scale.

[0018] Indeed, such purification operations have the disadvantage of needing to be carried out repeatedly to sufficiently reduce the impurity levels and, when the impurities are malodorous, to minimize the odors generated by certain impurities such as acetic acid, which are unpleasant and unsuitable for cosmetic use. Furthermore, the formation of sodium chloride during the neutralization step necessitates washing operations involving the addition of water, organic solvents, particularly alcohols, and possibly distillation to ensure its proper removal.

[0019] Such purification operations, especially when repeated, thus have the disadvantage of reducing yield, generating additional organic effluents, increasing the number of steps and / or being tedious to implement on an industrial level, both to reduce the content of organic acid, in particular acetic acid, and to reduce the content of salts, for example sodium chloride, in the final cosmetic active ingredient intended for the formulation of cosmetic products.

[0020] Furthermore, the use of organic solvents, particularly aprotic (a)polar organic solvents, during washing operations often has the drawback of not sufficiently reducing impurities and necessitating additional washing or neutralization operations, or even purification by chromatography and / or crystallization, which can further reduce yield. Such additional operations are cumbersome to implement on an industrial scale. In addition, residual levels of organic solvent(s) may persist in the cosmetic active ingredient solutions used in the final cosmetic formulations, which is undesirable.

[0021] It follows that the purification operations classically implemented in the processes for preparing C-glycosides derivatives do not lead to a yield and degree of purity that are sufficiently satisfactory, in particular for industrial-scale, reproducible and robust manufacturing for use in the field of cosmetics.

[0022] In view of the above, there is therefore a real need to implement a new process for preparing C-glycosides derivatives, which does not have the disadvantages mentioned above, leading in particular to an improved degree of purity, a higher yield and whose implementation is more optimized, specifically on an industrial level, in terms of product quality on an industrial scale, number of purification steps, implementation and / or organic effluents generated.

[0023] In other words, one of the aims of the present invention is in particular to propose a process for preparing one or more C-glycoside derivatives, in which impurities are minimized in order to be able to be effectively implemented on an industrial scale for cosmetic applications.

[0024] In particular, one of the aims of the present invention is to propose a process for preparing one or more C-glycoside derivatives in which impurities, including those likely to generate an unpleasant or bothersome odor, for example a pungent and strongly vinegary odor, in particular from the synthesis step, are minimized in order to be able to be effectively implemented on an industrial scale for cosmetic applications.

[0025] The present invention therefore relates in particular to a method for preparing at least one compound of the following formula (I): HAS -A. bA (I)

[0026] Formula (I) wherein: - SA' represents a monosaccharide or polysaccharide group comprising up to 20 sugar units, in particular up to 6 sugar units, preferably a monosaccharide, disaccharide or trisaccharide, more preferably a monosaccharide, in the form of pyranose and / or furanose and of the L and / or D series, said monosaccharide or polysaccharide group being substituted by at least one free hydroxyl group, and optionally at minus an amine group possibly protected in particular by an acetyl group R'-C(Y)- with R' representing a hydrogen atom, or a (Ci-C6)alkyl group such as methyl, and Y represents O, S, preferably O, - the bond between SA' and CH2-X is a C-anomeric bond, - X represents a divalent radical -C(O)- or -CH(OR)-, - R represents a hydrogen atom, an alkyl group in the form Ci-Cio, of preferably a C1-C4, such as methyl, or an alkyl(Ci-C4)carbonyl group such as acetyl, preferably a hydrogen atom; - Ri represents a hydrocarbon chain, saturated or unsaturated, linear or branched, cyclic or acyclic, preferably acyclic, in Ci-Cio, preferably in CrC4, more preferably saturated, in particular in Ci,

[0027] as well as one of its optical isomers, geometric isomers, and / or one of its solvates such as hydrates;

[0028] said process comprising: - at least one reaction step (i) proceeding according to the following synthesis scheme (A): gin (IA) gv)

[0029] synthesis route (A) in which: • Ri and R2 are identical or different; with R2 having the same meaning as Ri in formula (I), • SA' has the same meaning as in formula (I), • D+ is an organic or inorganic cation derived from the alkali agent; preferably D+ is an inorganic cation,

[0030] said reaction step (i) being carried out in aqueous media in the presence of: • of at least one compound of formula (II), • of at least one compound of formula (III), and • of at least one alkali agent in an equimolar quantity or in excess, relative to the compound of formula (II), preferably in excess

[0031] to lead to the formation of at least one compound of formula (IA) and at least one compound of formula (IV); - optionally, at least one reaction step (ii) of at least one of said compound of formula (IA) in a preferably aqueous medium to lead to the formation of at least one compound corresponding to the following formula (IB): GOLD (IB)

[0032] Formula (IB) in which: - SA', Ri and R have the same meanings as in formula (I); - at least one purification (P) of the reaction medium including at least said compound of formula (IV), carried out in aqueous medium, comprising: • at least one processing step (PI) implemented with at least one cationic ion exchange resin to convert at least said compound of formula (IV) into a compound of formula (IV') according to the following scheme: 0 O 1 _ —. 1 Rg-”' '0 0' said treatment step (PI) being carried out at a pH strictly lower than the pKa of the compound of formula (IV') or lower than the lowest pKa of the compounds of formula (IV') if several are present, • at least one separation step (P2) of at least of said compound of formula (IV') from the reaction medium.

[0033] The "bond between SA' and CH2-X" which "is a bond of C-anomeric nature" means that the part of the sugar motif SA' is linked to the rest of the molecule via the methylene group -CH2- by a carbon-carbon bond CC (i.e. carbon of sugar SA'-carbon of methylene -CH2-) and not by an oxygen-carbon bond OC (i.e. not by an oxygen of sugar SA' - carbon of methylene -CH2-).

[0034] For the purposes of the present invention, SA' comprises a monosaccharide or polysaccharide SA group comprising up to 20 sugar units, as defined above; SA being substituted by at least one free hydroxy group.

[0035] In other words, SA' has the same meaning as SA and includes at least one free hydroxy group (-OH).

[0036] For the purposes of the present invention, a compound of formula (IA) is a compound of formula (I) in which X corresponds to a divalent radical -C(O)-.

[0037] For the purposes of the present invention, a compound of formula (IB) is a compound of formula (I) in which X corresponds to a divalent radical -CH(OR)- with R such that defined previously, preferably R represents a hydrogen atom.

[0038] In other words, the invention relates to a process for preparing one or more C-glycoside derivatives of formula (I), as described above, comprising at least one purification (P), carried out in an aqueous reaction medium, intended to minimize at least significantly the levels of ionic impurities of formula (IV) from the synthesis step (i).

[0039] Thus the purification step (P) has the advantage of being flexible to implement during the preparation of at least one compound of formula (I).

[0040] Indeed, the purification step (P) can be carried out at least once between the reaction step (i) and the reaction step (ii) and / or after at least one reaction step (ii).

[0041] According to one embodiment, the purification step (P) is carried out at least once after the reaction step(s) (i).

[0042] According to another embodiment, the purification step (P) is carried out at least once after the reaction step(s) (ii).

[0043] According to a particular embodiment, the purification step (P) is carried out at least once after step or steps (i) and the process of the invention does not include step ii).

[0044] According to another embodiment, the process of the invention comprises at least one step i) preferably one step i), and at least one step ii) preferably one step ii), and the purification step (P) is carried out at least once after at least one step (i) without being carried out after step or steps (ii).

[0045] According to yet another embodiment, the process of the invention comprises at least one step i) preferably one step i), and at least one step ii) preferably one step ii), and the purification step (P) is carried out at least once after at least one step (ii) without being carried out after step or steps (i).

[0046] According to another embodiment, the process of the invention comprises at least one step i) preferably one step i), and at least one step ii) preferably one step ii), and the purification step (P) is carried out at least once after at least one step (i) and at least once after at least one step (ii).

[0047] According to a preferred embodiment, the process of the invention comprises a step i), and a step ii), and the purification step (P) is carried out at least once after step (i) without being carried out after step or steps (ii).

[0048] The purification (P) is thus carried out in an aqueous reaction medium, that is to say in a reaction medium free from any organic solvent as described below.

[0049] Thus the purification (P) according to the invention is free from any washing operation carried out with at least one organic solvent as described below.

[0050] The process according to the invention thus makes it possible to achieve the objectives as described below. before, that is to say that it leads to one or more compounds of formula (I), having a high degree of purity with a satisfactory yield while presenting an industrially optimized implementation, in particular robust and reproducible, especially compared to the processes classically implemented in the prior art.

[0051] In particular, the process according to the invention has the advantage of minimizing impurities, including those that usually cause a marked and unpleasant odor, such as a pungent and strongly vinegary odor, which are particularly difficult to eliminate in the processes conventionally implemented in the prior art.

[0052] More particularly, the treatment step (PI) is a neutralization step which at least significantly reduces the levels of salts formed during the reaction step (i), i.e. the levels of the compound of formula (IV).

[0053] In other words, the treatment step (PI) makes it possible to significantly convert at least the compound of formula (IV) into a compound of formula (IV') and then the separation step (P2) makes it easier to reduce the content of the compound of formula (IV') without having to use an organic solvent.

[0054] Thus the process according to the invention, in particular the purification step (P), has in particular the advantage of not using an organic solvent to reduce the content of impurities from the reaction step (i) which greatly improves its environmental footprint while being easy to implement on an industrial level.

[0055] The process according to the invention then advantageously makes it possible to reduce the quantities of perfumes to be used to mask or neutralize odors that may be bothersome during the preparation of a cosmetic formulation using at least one compound of formula (I).

[0056] The process according to the invention also makes it possible to reduce organic effluents at the reactor outlet and to limit the numerous washing operations conventionally implemented in the processes described in the prior art.

[0057] The process according to the invention has in particular an implementation that is easier to optimize on an industrial level than conventional prior art processes, in particular those involving the successive implementation of several operations to reduce impurities as much as possible, which makes it possible to treat the synthesis reaction and the purification in the same reactor having a suitable format.

[0058] The process according to the invention makes it possible to do without the implementation of additional purification steps carried out by chromatography and / or crystallization, which are not suitable on an industrial level and / or which are likely to impair the yield.

[0059] The process according to the invention thus makes it possible to achieve a gain in the number of purification steps to be implemented at the end of the synthesis reaction i) and / or ii) to reduce the impurity content of the compound (I).

[0060] Furthermore, when the process according to the invention implements a reduction step ii), carrying out at least one purification step (P) or (PI) at the end of step i) prior to ii) greatly facilitates obtaining compounds of formula (I) with X = -CH(OR)- with a very good yield and very good purity.

[0061] The process according to the invention also has the advantage of easily controlling target impurity levels, which allows obtaining several grades of a compound of formula (I), depending on the desired impurity content.

[0062] The process according to the invention thus makes it easier to control the levels of impurities.

[0063] The invention also relates to a method for purifying an aqueous medium comprising at least one compound corresponding to formula (I), as defined above, and at least one compound of formula (IV), as defined above, comprising: • at least one processing step (PI) implemented with at least one cationic ion exchange resin to convert at least said compound of formula (IV) into a compound of formula (IV') according to the following scheme:

[0064] said treatment step (PI) being carried out at a pH strictly lower than the pKa of the compound of formula (IV') or lower than the lowest pKa of the compounds of formula (IV') if several are present, and • at least one separation step (P2) of at least of said compound of formula (IV') from the reaction medium.

[0065] Other objects, features, aspects and advantages of the invention will become even clearer upon reading the description and example that follows.

[0066] In what follows, and unless otherwise indicated, the bounds of a range of values ​​are included in that range, in particular in the expressions "between" and "ranging from ... to ...".

[0067] Furthermore, the expression "at least one" used in this description is equivalent to the expression "one or more".

[0068] Furthermore, the expression "at least" used in this description is equivalent to the expression "greater than or equal to". Finally, in a manner known per se, a compound or group in "Cn" or in "Cn" is designated by a compound or group containing in its chemical structure "n" carbon atoms.

[0069] For the purposes of the present invention, the terms “purification (P)” and “purification step (P)” are used interchangeably.

[0070] For the purposes of the present invention, the terms "alkaline agent" and "alkalinizing agent" are used interchangeably.

[0071] The alkalizing agent(s) may be mineral alkaline agents, preferably chosen from the group consisting of alkali metal hydroxides or alkaline earth metal hydroxides, such as lithium hydroxides, sodium hydroxide, potassium hydroxide, alkali or alkaline earth metal (bi)carbonates such as sodium or potassium (bi)carbonates, and mixtures thereof.

[0072] The alkalizing agent(s) may be organic alkali agents, preferably chosen from the group consisting of mono(Ci-C6)(hydroxy)alkylamine, di(Ci-C6)(hydroxy)alkylamine, tri(Ci-C6)(hydroxy)alkylamine (preferably tri(Ci-C6)(hydroxy)alkylamine), saturated or unsaturated cyclic amines, aromatic such as pyridine, or non-aromatic, optionally substituted by one or more (Ci-C4)alkyl groups such as tetrahydropyridines optionally substituted by one or more (Ci-C4)alkyl groups, piperidines optionally substituted by one or more (Ci-C4)alkyl groups, or piperazines optionally substituted by one or more (Ci-C4)alkyl groups. Preferably, organic alkali agents are organic amines, especially tertiary ones, such as tri(Ci-C6)alkylamines.

[0073] Preferably, the alkalizing agents are chosen from the group consisting of alkali or alkaline-earth metal hydroxides, in particular sodium hydroxide, alkali or alkaline-earth metal (bi)carbonates, in particular sodium or potassium (bi)carbonates and organic amines, preferably tertiary, such as triethylamine or diisopropylethylamine.

[0074] Preferably, the alkalizing agents are mineral.

[0075] More preferably, the alkalizing agents are mineral and are chosen from the group consisting of alkali or alkaline-earth metal hydroxides, alkali or alkaline-earth metal (bi)carbonates, and their mixtures, in particular alkali or alkaline-earth metal hydroxides, in particular sodium hydroxide.

[0076] The acidifying agents that can be used in the process according to the invention are all acidification methods known to those skilled in the art, such as bipolar electrodialysis or the addition of mineral acidifying agents, in particular mineral acids such as sulfuric acid, phosphoric acid, sulfonic acid, phosphonic acid, H+Hal acids, where Hal represents a chosen halogen atom in the group consisting of chlorine, bromine and iodine, preferably H+Hal acids with Hal representing preferably a chlorine atom; preferably by addition mineral acidifying agents, in particular mineral acids such as sulfuric acid, phosphoric acid, sulfonic acid, phosphonic acid, H+Hal acids with Hal representing a halogen atom chosen from the group consisting of chlorine, bromine and iodine, preferably H+Hal acids with Hal representing preferably a chlorine atom

[0077] More preferably, the acidifying agent is hydrochloric acid.

[0078] Process for preparing at least one compound of formula H)

[0079] As previously stated, the method according to the invention comprises: - at least one reaction step (i) taking place in an aqueous medium and according to the reaction scheme (A), as described above, in the presence of: • of at least one compound of formula (III), preferably in an equimolar quantity or in excess relative to the compound of formula (II), preferably in excess, and • of at least one alkali agent, preferably at least one mineral alkali agent, in an equimolar quantity or in excess, preferably in excess, relative to the compound of formula (II),

[0080] to lead to the formation of at least one compound of formula (IA) (i.e. a compound corresponding to formula (I) in which X corresponds to a divalent radical -CO-, and at least one compound of formula (IV); - possibly at least one reaction step (ii) leading to the formation of at least one compound of formula (IB) (i.e. a compound corresponding to formula (I) in which X corresponds to a divalent radical -CH(OR)- with preferably R representing a hydrogen atom), - at least one purification (P) of the reaction medium comprising at least the compound of formula (IV), carried out in aqueous medium, comprising: • at least one processing step (PI) implemented with at least one cationic ion exchange resin to convert at least said compound of formula (IV) into a compound of formula (IV') according to the following scheme: OG HE *-----------H said treatment step (PI) being carried out at a pH value less than strictly the pKa of the compound with formula (IV') or less than the lowest pKa of the compounds with formula (IV') if several are present, at least one separation step (P2) of at least of said compound of formula (IV') from the reaction medium. Reaction step (i)

[0081] Advantageously, the reaction step(s) (i) are carried out in an aqueous medium, in presence : • of at least one compound of formula (II), • of at least one compound of formula (III), preferably, the molar ratio of compound(s) of formula (III) / compound(s) of formula (II) is greater than or equal to 1, preferably between 1 and 5, more preferably between 1 and 4, even more particularly between 1 and 3, better between 1 and 2, in particular ranging from 1 to 1.5; according to a particular embodiment, the molar ratio of compound(s) of formula (III) / compound(s) of formula (II) is greater than 1; of at least one alkaline agent, preferably at least one alkali metal agent as described above, preferably mineral, more preferably chosen from the group consisting of alkali or alkaline earth metal hydroxides, alkali or alkaline earth metal (bi)carbonates, and mixtures thereof; in particular alkali or alkaline earth metal hydroxides, such as sodium hydroxide, the alkali agent being in an equimolar quantity or in excess preferably, the molar ratio of alkali agent(s) / compound(s) of formula (II) is greater than or equal to 1, preferably between 1 and 5, more preferably between 1 and 4, even more particularly between 1 and 3, better between 1 and 2; according to a particular embodiment, the molar ratio of alkali agent / compound of formula (II) is greater than 1, Preferably, reaction step (i) takes place: • at a temperature ranging from 20°C to 80°C, preferably at a temperature ranging from 20°C to 70°C, more preferably at a temperature ranging from 30°C to 70°C, better from 30°C to 60°C, even better at a temperature ranging from 35°C to 45°C, Preferably, the duration of the reaction varies: • from 10 minutes to 10 hours, preferably from 20 minutes to 5 hours, more preferably from 30 minutes to 4 hours, even more preferably from 45 minutes to 3 hours. • Preferably, reaction (i) is carried out at atmospheric pressure;

[0082] Preferably, the reaction step(s) (i) are carried out in an aqueous medium and comprise successively: • preferably the addition of at least one compound of formula (II) in an aqueous medium, particularly at a temperature ranging from 20°C to 80°C, • preferably, the addition of at least one compound of formula (III) to the aqueous medium comprising at least one compound of formula (II), • - optionally, the temperature is advantageously reduced by at least 5°C, in particular at least 10°C, preferably at least 20°C, before the addition of at least one alkaline agent • preferably, the addition of at least one alkali agent, preferably mineral, in an equimolar quantity with respect to the compound of formula (II) or in excess, preferably in excess, as described above, maintaining the temperature preferably below or equal to 60°C, better below or equal to 50°C, even better below or equal to 45°C, • Preferably, the reaction medium comprising at least one compound of formula (II), at least one compound of formula (III) and at least one alkali agent, is maintained at the final temperature of addition of at least one alkali agent and / or heated to the reaction temperature as described above, • Optionally, after reaction (i), the reaction medium may be cooled by at least 5°C, preferably by at least 10°C, more preferably by at least 15°C.

[0083] Preferably, at the end of the reaction step(s) (i), the pH can be adjusted to a value less than or equal to 8.5, and greater than or equal to 2.5, preferably is adjusted in a range from 2.5 to 8.5.

[0084] The pH can be adjusted by any means of acidification known to those skilled in the art, such as the implementation of at least one acid resin and / or by adding at least one acidifying agent as described above, preferably mineral, more preferably chosen from the group consisting of mineral acids as described above.

[0085] According to a particular embodiment, the pH is adjusted by at least one acid resin and optionally by adding at least one acidifying agent as described above, preferably mineral, more preferably chosen from the group consisting of mineral acids as described above.

[0086] According to a preferred embodiment, the process according to the invention comprises a step i). Purification step (P)

[0087] In accordance with the present invention, the purification step (P) is carried out on an aqueous reaction medium comprising at least one impurity of formula (IV).

[0088] The purification step (P) can thus be carried out once or several times on an aqueous reaction medium comprising at least one impurity of formula (IV).

[0089] According to one embodiment, the purification step (PI) is carried out once or several times and the purification step (P2) is carried out at least once after at least one step (PI).

[0090] The purification (P) can thus be carried out on an aqueous reaction medium from the reaction step (i) and / or on an aqueous reaction medium from at least one reaction step (ii).

[0091] In other words, the purification(s) (P) can / can be implemented at least once between a reaction step (i) and at least one reaction step (ii), and / or at least once after at least one reaction step (ii), for example after one and / or two reaction steps (ii).

[0092] According to one embodiment, the purification step (P) is carried out at least once after the reaction step(s) (i).

[0093] According to another embodiment, the purification step (P) is carried out at least once after the reaction step(s) (ii).

[0094] According to a particular embodiment, the purification step (P) is carried out at least once after step(i) and the process of the invention does not include step ii).

[0095] According to another embodiment, the process of the invention comprises at least one step i) preferably one step i), and at least one step ii) preferably one step ii), and the purification step (P) is carried out at least once after at least one step (i) without being carried out after step or steps (ii).

[0096] According to yet another embodiment, the process of the invention comprises at least one step i) preferably one step i), and at least one step ii) preferably one step ii), and the purification step (P) is carried out at least once after at least one step (ii) without being carried out after step or steps (i).

[0097] According to another embodiment, the process of the invention comprises at least one step i) preferably one step i), and at least one step ii) preferably one step ii), and the purification step (P) is carried out at least once after at least one step (i) and at least once after at least one step (ii).

[0098] According to a preferred embodiment, the process of the invention comprises a step i), and a step ii), and the purification step (P) is carried out at least once after step (i) without being carried out after step (ii) or steps (ii).

[0099] According to one embodiment, the purification step (PI) is carried out at least once after the reaction step(s) (i).

[0100] According to another embodiment, the purification step (P2) is carried out at least once after the reaction step(s) (ii).

[0101] According to another embodiment, the process of the invention comprises at least one step i) preferably one step i), and at least one step ii) preferably one step ii), and a purification step (PI) is carried out at least once after at least one step (i) and a purification step (P2) is carried out at least once after at least one step (ii).

[0102] Preferably, the purification (P) is carried out at least once between the reaction step (i) and at least one reaction step (ii).

[0103] In other words, when at least one step ii) exists, the purification step (P) can be implemented at least before and / or at least after the reaction step(s) (ii), preferably at least before the reaction step(s) (ii).

[0104] Preferably, the purification (P) is carried out at least once after the reaction step (i).

[0105] When several steps i) are implemented in the process, at least one purification (P) can be carried out at the end of each of the steps i), or at least one purification step (P) can be carried out only at the end of the last step i).

[0106] For the purposes of this invention, "a purification step (P) or a purification (P) carried out or performed in an aqueous reaction medium" means a purification step (P) or a purification (P) carried out or performed in any aqueous medium preferably free from any water-miscible organic solvent and comprising at least one compound of formula (IV), which may be obtained from reaction step (i) and / or from at least one reaction step (ii), preferably in an aqueous medium free from any organic solvent.

[0107] Thus the purification (P) is carried out in an aqueous reaction medium, comprising at least one compound of formula (IV), which is preferably free from any water-miscible organic solvent, i.e. in an aqueous medium not comprising any water-miscible organic solvent.

[0108] In other words, the treatment step(s) (PI) and the separation step(s) (P2) are carried out in an aqueous reaction medium preferably free from any water-miscible organic solvent and comprising at least one compound of formula (IV) and / or (IV').

[0109] In other words, the treatment step (PI) and the separation step (P2) preferably do not use water-miscible organic solvents.

[0110] Preferably, the purification (P) is carried out in an aqueous reaction medium free from any organic solvent.

[0111] In other words, purification (P) is preferentially carried out in water.

[0112] In other words, the treatment step (PI) and the separation step (P2) do not preferentially use organic solvent.

[0113] According to a preferred feature of the present invention, the purification (P) is free from any washing step or operation with at least one water-miscible organic solvent, preferably from any washing step or operation with at least one organic solvent.

[0114] More preferably, the purification (P) does not use an organic solvent chosen from the group consisting of dichloromethane, diethyl ether, ethanol and mixtures thereof.

[0115] In particular, purification (P) does not involve any organic solvent selected from the group consisting of ethanol, methanol, isopropanol, butanol, isobutanol, tert-butanol and mixtures thereof.

[0116] According to one embodiment, the reaction medium of the purification step (P) does not comprise at least one organic solvent as defined above, in particular chosen from the group consisting of dichloromethane, ethanol, methanol, toluene, isopropanol and mixtures thereof, in particular dichloromethane, ethanol and mixtures thereof.

[0117] According to one embodiment, the purification (P) does not involve an organic solvent selected from the group consisting of dichloromethane, diethyl ether, ethanol, methanol, isopropanol, butanol, isobutanol, ter-butanol, toluene, isopropanol and mixtures thereof.

[0118] More specifically, purification (P) does not involve an organic solvent chosen from the group consisting of apolar aprotic organic solvents, such as those described above, C1-C3 alcohols, and mixtures thereof

[0119] The purification (P) is in particular free from organic solvents selected from the group consisting of heptane, 1,4-dioxane, benzene, xylene, tetrachloroethylene (C12C=C12C), toluene, carbon disulfide (CS2), trichloroethylene (C12C=CHC1), diethyl ether (Et2O), diisopropyl ether, tert-butyl ether, ethyl acetate (CH3C(O)OEt or AcOEt), butyl acetate, isopropyl acetate, methylpyrrolidone, cyclopentyl methyl ether, ketones such as methyl ether ketone, methyl isobutyl ketone, methyl propionate, butanol, isobutanol, tert-butanol, pentanol, and dimethyl ether. (DME), tetrahydrofuran (THF), methyltetrahydrofuran (2-MeTHF), dichloromethane (CH2C12), dichloroethane (C1CH2CH2C1), and mixtures thereof.

[0120] The purification (P) is in particular free from (a)polar aprotic organic solvents, such as apolar aprotic organic solvents, preferably having a constant dielectric ranging from 1 to 11.

[0121] The purification (P) is more particularly free of (a)protic (a)polar organic solvent.

[0122] According to a general feature of the invention, the purification step (P) is in particular free from at least one step of washing the reaction medium, from a step (i) and / or from at least one step (ii), carried out with at least one organic solvent as defined above.

[0123] Preferably, at the end of the reaction step(s) (i) and / or at the end of at least one reaction step (ii), the process does not include at least one step of washing the reaction medium carried out with at least one organic solvent as defined above.

[0124] Thus, in accordance with an advantage of the present invention, no treatment step (PI) is implemented in addition to at least one washing step with at least one organic solvent, preferably at least one organic solvent as defined above. Processing step (PI)

[0125] The treatment step(s) (PI) of the reaction medium comprising at least one compound of formula (IV) are carried out with at least one cationic ion exchange resin, preferably at least one weak cationic resin, for example a resin having carboxylic active groups, and / or at least one strong cationic resin, preferably at least one sulfonic resin.

[0126] In other words, the aqueous reaction medium, which may be obtained from at least one step (i) and / or at least one step (ii), is brought into contact with at least one cationic ion exchange resin, preferably at least one weak cationic resin, for example a resin having carboxylic active groups, and / or at least one strong cationic resin, preferably at least one sulfonic resin.

[0127] Preferably, the treatment step(s) (PI) are carried out with at least one cationic resin having carboxylic groups and / or at least one sulfonic resin, preferably at least one sulfonic resin.

[0128] Preferably, the treatment step(s) (PI) are carried out with at least one cationic resin comprising one or more carboxylic groups and / or one or more sulfonic groups.

[0129] Preferably, the treatment step(s) (PI) of the reaction medium comprising at least one compound of formula (IV) are carried out with at least one sulfonic resin.

[0130] Preferably, the cationic ion exchange resin is a sulfonic resin comprising one or more sulfonic groups (SO3H) and / or one or more sulfonate groups (-SO3), more preferably one or more groups sulfonates (-SO3).

[0131] The treatment step(s) (PI) are implemented at a pH value strictly lower than the pKa of the compound corresponding to formula (IV').

[0132] When the reaction medium to be treated by at least one treatment step (PI) contains several different compounds of formula (IV'), the treatment step(s) (PI) are carried out at a pH value strictly lower than the lowest pKa of the compounds of formula (IV').

[0133] When the process includes several steps i), the treatment step (PI) can be carried out at the end of each step i) or at the end of the last step i).

[0134] When the process includes several steps ii), the treatment step (PI) can be carried out at the end of each step ii) or at the end of the last step ii).

[0135] According to one embodiment, the process comprises a single step (i) and step (PI) is carried out at least once after step (i).

[0136] According to another embodiment, the process comprises a single step (ii) and step (PI) is carried out at least once after step (ii).

[0137] According to a preferred embodiment, the process comprises a single step (i) and a single step (ii) and step (PI) is carried out one or more times between step (i) and step (ii), preferably once.

[0138] Preferably, the treatment step(s) (PI) of the reaction medium from reaction step (i) is carried out in a pH range of 1.5 to 6, preferably from 2 to 4.5, more preferably from 2 to 3.5, better in a pH range of 2.5 to 3.5.

[0139] The processing step (PI) can be carried out once or several times, preferably once. Separation stage (P2)

[0140] The separation step(s) (P2) can be implemented immediately after the step(s) (PI).

[0141] According to one embodiment, steps (PI) and (P2) are implemented successively after at least one step (i).

[0142] According to another embodiment, steps (PI) and (P2) are implemented successively after at least one step (ii).

[0143] According to yet another embodiment, at least one step (PI) is implemented after at least one step (i), and at least one step (P2) is implemented after at least one step (ii).

[0144] According to another embodiment, the process of the invention implements at least one step (PI) after at least one step (i) and implements at least one step (P2) after at least one step (i) and after at least one step (ii).

[0145] Preferably, the separation step(s) (P2) are implemented by dis- tillation, electrodialysis, preferably by vacuum distillation, more preferably by vacuum distillation at a temperature that may vary from 30 to 80°C, preferably from 30°C to 55°C, preferably from 30°C to 50°C.

[0146] Preferably, the separation step(s) (P2) of at least said compound of formula (IV') from the reaction medium from step (PI) are carried out by distillation, electrodialysis, preferably by vacuum distillation.

[0147] Preferably, the separation step(s) (P2) of at least said compound of formula (IV') from the reaction medium from step (PI) are carried out by distillation, preferably by vacuum distillation, at a temperature that may vary from 30 to 80°C, preferably from 30 to 55°C, preferably from 30 to 50°C.

[0148] According to one embodiment, the separation step (P2) can be implemented several times.

[0149] The separation step (P2), preferably a distillation, is advantageously carried out several times depending on the impurity content (IV') that one wishes to achieve in the composition comprising the compound of formula (I).

[0150] In other words, the separation step (P2), preferably a distillation, can advantageously be implemented depending on the grade of the compound(s) of formula (I) that one wishes to obtain.

[0151] Preferably, at the end of the separation step (P2) or the last purification step (P2), the content of compound(s) of formula (IV') is less than or equal to 10% by weight, preferably less than or equal to 5% by weight, more preferably varies from 1 to 5% by weight, better varies from 1 to 2% by weight, relative to the total weight of the dry extract containing the compound(s) of formula (I).

[0152] At the end of the separation step (P2) or the last separation step (P2), the content of the compound(s) of formula (IA) varies from 20 to 70%, preferably from 30 to 60% by weight, relative to the total weight of the dry extract.

[0153] According to one embodiment, water may be added between the treatment step (PI) or the last treatment step (PI) and at least one separation step (P2).

[0154] Preferably, at the end of the treatment step (PI) or the last treatment step (PI), water may be added and the separation step (P2), preferably a distillation, is carried out at least once to separate at least the compound of formula (IV') and water from the reaction medium.

[0155] Preferably, the addition of water and the separation step (P2) can be implemented repeatedly, which makes it easier to separate the compound of formula (IV') from the reaction medium.

[0156] Additional steps during the purification step (P)

[0157] The purification (P) may further include one or more additional steps, different from steps (PI) and (P2).

[0158] The purification (P), carried out in an aqueous reaction medium comprising at least the compound of formula (IV), may include, simultaneously or sequentially, preferably sequentially, in particular before or after the treatment step (PI), in particular before the treatment step (PI), at least one neutralization step (PO) of all or part of the excess alkali present in the reaction medium from step (i).

[0159] Preferably, at least one purification (P), carried out in an aqueous reaction medium, comprises: • at least one treatment step (PO) to neutralize all or part of the excess alkali present in the reaction medium from at least one step (i), • at least one treatment step (TP) of the reaction medium from step (i) with at least one cationic ion exchange resin, as defined above, implemented at a pH value strictly lower than the pKa of the compound of formula (IV) or lower than the lowest pKa of the compounds of formula (IV) if several are present, • at least one separation step (P2) of at least one of said compound(s) of formula (IV') from the reaction medium, • possibly at least one separation step (P'O) of the compound(s) of formula (III) present in the reaction medium at the end of reaction(s) (i).

[0160] The purification step (P) optionally includes at least one further step of activating the cationic ion exchange resin so that it is in acidic form.

[0161] The resin activation step can be carried out before the neutralization step (PO) and / or before the treatment step (PI).

[0162] According to one embodiment, the neutralization step (PO) is carried out with at least one cationic ion exchange resin at a pH value strictly lower than the pKa of the compound of formula (IV') or by adding at least one acidifying agent, organic or mineral, preferably mineral and more preferably chosen from the group consisting of mineral acids as described above, to the reaction medium from step (i).

[0163] Preferably, the neutralization step (PO) of all or part of the excess alkali is carried out with at least one cationic ion exchange resin at a pH value strictly lower than the pKa of the compound of formula (IV') or at a value strictly lower than the lowest pKa of said compounds of formula (IV'), preferably in a pH range from 1.5 to 6, preferably from 2 to 4.5, more preferably from 2 to 3.5, better in a pH range from 2.5 to 3.5.

[0164] The cationic ion exchange resin, which may be used in the treatment step (PO), may be the same or different, preferably the same as that used in the treatment step (PI).

[0165] Alternatively, the neutralization step (PO) of all or part of the at least one alkali can be carried out by adding at least one acidifying agent, organic or mineral, preferably mineral, to the reaction medium from step (i).

[0166] Preferably, the separation step (P'O) of the compound of formula (III) is carried out after the neutralization step (PO).

[0167] More preferably, the separation step (P'O) of the compound of formula (III) can be carried out by distillation.

[0168] Before the possible implementation of at least one reaction step (ii), the pH of the reaction medium may be modified by the addition of at least one mineral acidifying agent or an alkaline agent, mineral or organic.

[0169] Preferably, the pH of the reaction medium can be modified by adding at least one mineral acidifying agent, in particular of the type of mineral acids such as sulfuric acid, phosphoric acid, sulfonic acid, phosphonic acid, H+Hal acids, with Hal representing a halogen atom chosen from the group consisting of chlorine, bromine and iodine, more preferably the acidifying agent is hydrochloric acid. Reaction step (ii)

[0170] The preparation process may optionally further comprise at least one reaction step (ii) of at least one of said compound of formula (I) in which X corresponds to a divalent radical -C(O)- (i.e. a compound of formula (IA)) to form at least one compound of formula (I) in which X corresponds to a divalent radical -CH(OR)- (i.e. a compound of formula (IB)).

[0171] According to an advantageous embodiment, the process according to the invention further comprises at least one reaction step (ii) of at least one of said compound of formula (IA) to form at least one compound of formula (IB). Reduction stage (iil)

[0172] The reaction step (ii) is preferably a reduction step (iil) taking place in aqueous medium according to the following synthesis route (B): Reduction SA'' fl -------------SA" Y Oh! (AI) (FB)

[0173] synthesis route (B) in which: • SA' and RI have the same meanings as in formula (I).

[0174] For the purposes of the present invention, a compound of formula (l'B) is a compound of formula (IB) in which R represents a hydrogen atom.

[0175] In other words, a compound of formula (l'B) is a compound of formula (I) in which X corresponds to a divalent radical -CH(OR)- with R representing a hydrogen atom.

[0176] Preferably, the preparation process according to the invention comprises: - at least one reaction step (i), as described previously, - at least one reduction step (ül), taking place in an aqueous medium according to the synthesis route (B) as defined previously, - at least one purification step (P), as described above, implemented before and / or after the reduction step (iil).

[0177] The reduction step of the carbonyl group to give an alcohol group is carried out by a conventional reduction method known to those skilled in the art. For example, see (Adv. Org. Chem. J. March, 4th ed. John Wiley & Son, pp. 910-919, (1992). At least one reduction step (iil) may be a reduction carried out in the presence of one or more hydrides, in particular borohydrides such as NaBH4, NaBH3CN, an enzymatic reduction, or a reduction by catalytic hydrogenation.

[0178] Preferably, at least one reduction step (iil) is a reduction by catalytic hydrogenation.

[0179] In other words, at least one reduction step (iil) is advantageously a hydrogenation carried out in the presence of at least one catalyst and possibly an acidifying agent. The hydrogenation can, for example, be carried out under conditions described in the literature. Heterocycles M. Hashimoto, M. Takahashi 77 (1), 227-231 (2009).

[0180] The catalyst is preferably a metallic catalyst, such as ruthenium (Ru), rhodium (Rh), platinum (Pt), iridium (Ir), nickel (Ni) or palladium (Pd), preferably ruthenium (Ru), more preferably a metallic catalyst, chosen from ruthenium (Ru), rhodium (Rh), platinum (Pt), iridium (Ir), better ruthenium (Ru).

[0181] Preferably, the catalyst is supported, preferably is supported ruthenium, such as on carbon (or graphite), on alumina, on ASi, on zeolite, or on barium sulfate (BaSO4).

[0182] According to one embodiment, hydrogenation is catalyzed by Pd on carbon (Pd / C) or Ru on carbon (Ru / C).

[0183] Preferably, the catalyst is chosen from the group consisting of ruthenium on carbon (Ru / C), ruthenium on alumina (Ru / Al), ruthenium on ASi, ruthenium on zeolite or ruthenium on barium sulfate (BaSO4).

[0184] Preferably, the catalyst is ruthenium (Ru), especially on carbon (Ru / C).

[0185] Preferably, at least one reduction step (ül) is carried out under a hydrogen pressure ranging from 2 to 100 bars, preferably from 3 to 50 bars, more preferably from 4 to 25 bars, even more preferably from 5 to 15 bars, better from 6 to 12 bars, such as 10 bars.

[0186] Preferably, at least one reduction step (ül) is carried out at a temperature ranging from 30 to 150°C, preferably at a temperature ranging from 40 to 100°C, more preferably at a temperature ranging from 65°C to 100°C.

[0187] Preferably, at least one reduction step (ül) takes place over a period ranging from 30 minutes to 30 hours, preferably from 45 minutes to 10 hours, in particular ranging from 1 hour to 7 hours.

[0188] Preferably, at least one reduction step (ül) is a reduction by catalytic hydrogenation in the presence of at least one catalyst, in particular ruthenium, under a hydrogen pressure of 2 to 100 bars and at a temperature of 30 to 150°C.

[0189] Preferably, at least one reduction step (ül) is a reduction by catalytic hydrogenation in the presence of at least one catalyst, in particular ruthenium, under a hydrogen pressure of 2 to 50 bars and at a temperature of 40 to 100°C.

[0190] Preferably, at least one reduction step (ül) is a reduction by catalytic hydrogenation in the presence of at least one catalyst, in particular ruthenium, under a hydrogen pressure of 2 to 25 bars and at a temperature of 65°C to 100°C.

[0191] Advantageously, at least one reduction step (ül) is carried out in an aqueous medium: - in the presence of: • of at least one compound of formula (I), in which X corresponds to a divalent radical -C(O)-, • of at least one catalyst, preferably chosen from the group consisting of palladium or ruthenium, in particular ruthenium on carbon, - under a hydrogen pressure varying from 2 to 50 bars, more preferably from 4 to 12 bars, such as 10 bars; - at a temperature ranging from 40 to 100°C, preferably in a temperature ranging from 65 to 120°C.

[0192] Following at least one reduction step (ül), the reaction medium can be cooled to a temperature ranging from 15 to 25 °C and then purged under nitrogen.

[0193] The reaction medium from step (iil) is then preferably filtered.

[0194] Preferably, the preparation process according to the invention comprises sively: • at least one reduction step (iil) as defined previously, • preferably, the reaction medium before, during or after the reduction step (iil) undergoes at least one treatment with carbon black, more preferably before or after the reduction step (iil), in particular before the reduction step (iil) the reaction medium undergoes at least one treatment with carbon black, possibly at a temperature ranging from 20 °C to 90 °C, • optionally, at least one step of adding at least one acidifying or alkalizing agent to the reaction medium resulting from the reduction step (iil), • Optionally, at least one concentration step (iil) of the compound of formula (IB) in the reaction medium from the reduction step (iil), • Preferably the concentration step (iil) is carried out by distillation, preferably under reduced pressure, • Optionally, at least one purification step such as filtration, • optionally, at least one step (iv) of adding at least one bacterium agent tericidal or bacteriostatic, preferably bacteriostatic, preferably glycol-derived such as propylene glycol, pentylene glycol, caprylyl glycol, • preferably, the bacteriostatic agent, in particular propylene glycol, is present in a content ranging from 2 to 50% by weight, preferably from 5 to 40% by weight, relative to the total weight of the mixture comprising at least the compound of formula (IB), and the bacteriostatic agent, • possibly, at least one purification step such as distillation.

[0195] For the purposes of this invention, "bio-based" means that the compounds described as "bio-based" are derived from compounds of plant origin. Addition step (ii2)

[0196] The reaction step (ii) can also be an addition or O-alkoxylation step (ii2) taking place in aqueous or non-aqueous media, according to the following synthesis route (Bl): (TB) (TB)

[0197] synthesis route (Bl) in which:

[0198] R corresponds to an alkyl group in CrCio, preferably in Ci-C4, such as methyl, or an alkyl(Ci-C4)carbonyl group such as acetyl.

[0199] Advantageously, the method according to the invention comprises: - at least one step (i) as defined above, - at least one reaction step (ii) corresponding to a reduction step (iil), as defined previously, - at least one reaction step (ii) corresponding to an addition step (ii2), as defined above, - at least one purification (P), as defined above, implemented at least between the reaction step (i) and the reduction step (iil), and / or at least after the reduction step (iil), preferably between the reduction step (i) and the addition step (ii2), and / or after the addition step (ii2).

[0200] According to another embodiment of the invention, the compounds (I”B) are obtained by adding at least one molar equivalent of at least one nucleophilic compound RG to at least one compound of formula (IA), with R as defined above and G represents an electron-deficient atom or group such as an alkali metal such as sodium, potassium, or lithium, or a magnesium halide such as MgCl, in particular this reaction is carried out under an inert atmosphere and in a preferably polar aprotic organic solvent, particularly an ethereal solvent such as diethyl ether, THF, followed by a hydrolysis reaction. Packaging of the compound of formula (I)

[0201] At the end of the process according to the invention, the compound of formula (I), in which X corresponds to a divalent radical -C(O)- or -CH(OR)-, can be conditioned in the form of a dry extract (solvent-free).

[0202] Preferably, at the end of the process according to the invention, the compound of formula (I), in which X corresponds to a divalent radical -C(O)- or -CH(OR)-, is in solution in a liquid which comprises a content of at least 25% by weight of active material of the compound of formula (I), preferably in a content ranging from 25 to 80% by weight, more preferably ranging from 25 to 75% by weight, more preferably ranging from 30 to 75% relative to the total weight of the solution.

[0203] Preferably, at the end of the process according to the invention, the compound of formula (I), in which X corresponds to a divalent radical -C(O)- or -CH(OR)-, is found in solution in a liquid which comprises a content of at least 20% by weight of active material of the compound of formula (I), preferably in a content of 20 to 90% by weight, more preferably of 25 to 80% by weight, more preferably of 25 to 75% relative to the total weight of the solution.

[0204] Preferably, at the end of the process according to the invention, the compound of formula (I), in which X corresponds to a divalent radical -C(O)- or -CH(OR)-, is in solution in a liquid which comprises a content of at least 25% by weight of active material (I), more preferably in a content ranging from 25 to 45% by weight relative to the total weight of the solution.

[0205] Preferably, at the end of the process according to the invention, the compound of formula (I), in which X corresponds to a radical -C(O)- or -CH(OR), is in solution in a liquid which comprises a content of at least 25% by weight of active material, more preferably in a content ranging from 25% to 75% by weight relative to the total weight of the solution.

[0206] According to one embodiment, the compound of formula (I) in which X corresponds to a divalent radical -C(O)- or -CH(OR)- is conditioned in a liquid and the pH is adjusted to a target value, preferably between 3.5 and 7, by adding at least one alkalizing agent or at least one acidifying agent. Chemical structure(s)

[0207] SA' may represent a monosaccharide group or a polysaccharide group comprising up to 6 sugar units, in the form of pyranose and / or furanose and of L and / or D series, of anomer a or b, and comprising at least one free hydroxy group, and possibly at least one amine group possibly protected.

[0208] Preferably, SA' represents a monosaccharide or a polysaccharide comprising up to 6 sugar units, in the form of pyranose and / or furanose and of L and / or D series, and comprising at least one free hydroxy group.

[0209] According to one embodiment, SA' is a monosaccharide group selected from the group consisting of glucose, galactose, mannose, xylose, fucose, arabinose, rhamnose, glucuronic acid, galacturonic acid, iduronic acid, N-acetylglucosamine, N-acetylgalactosamine and more particularly SA is a monosaccharide selected from the group consisting of D-glucose, D-galactose, D-mannose, D-xylose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine.

[0210] Preferably, SA' is a monosaccharide selected from the group consisting of glucose, xylose, N-acetylgalactosamine or fucose, in particular glucose, xylose or fucose, more particularly xylose.

[0211] More preferably, SA' is a monosaccharide group selected from the group consisting of D-glucose, D-xylose, N-acetyl-D-galactosamine or L-fucose, in particular D-glucose, D-xylose or L-fucose, more particularly D-xylose.

[0212] According to one embodiment, SA' is a polysaccharide group comprising up to 6 sucrose units and selected from the group consisting of D-maltose, D-lactose, D-cellobiose, D-maltotriose, a disaccharide combining a uronic acid selected from D-iduronic acid or D-glucuronic acid with a hexosamine selected from D-galactosamine, D-glucosamine, N-acetyl-D-galactosamine, N-acetyl-D-glucosamine, an oligosaccharide containing at least one xylose advantageously selected from xylobiose, methyl-beta-xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and preferably xylobiose which is composed of two xylose molecules linked by a beta-1-4 bond.

[0213] Preferably, SA' represents a monosaccharide.

[0214] Preferably, SA' represents a monosaccharide group selected from the group consisting of glucose, in particular D-glucose, xylose, in particular D-xylose, fucose, in particular L-fucose, arabinose, in particular L-arabinose, rhamnose, in particular L-rhamnose, glucuronic acid, in particular D-glucuronic acid, galacturonic acid, in particular D-galacturonic acid, iduronic acid, in particular D-iduronic acid, N-acetyl glucosamine, in particular N-acetyl-D-glucosamine, N-acetyl-galactosamine, in particular N-acetyl-D-galactosamine, and preferably SA is chosen from D-glucose, D-xylose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid.

[0215] Preferably, SA' represents a monosaccharide group chosen from the group by glucose, xylose, N-acetylgalactosamine or fucose, more preferably SA is chosen from the group consisting of glucose, xylose or fucose.

[0216] Preferably, SA' represents a monosaccharide group chosen from the group by D-glucose, D-xylose, N-acetyl-D-galactosamine or L-fucose, more preferably SA is chosen from the group consisting of D-glucose, D-xylose or L-fucose.

[0217] More preferably, SA' represents a xylose group and even more preferably D-xylose.

[0218] As previously stated, Ri represents a linear or branched, saturated or unsaturated, cyclic or acyclic hydrocarbon chain, in Ci-Cio, preferably in Ci-C6, more preferably in Ci-C4, in particular in Ci.

[0219] According to one embodiment, Ri represents a linear or branched, saturated or unsaturated, cyclic or acyclic, preferably acyclic, hydrocarbon chain in Ci-C6, more preferably in Ci-C4, in particular in Ci.

[0220] According to one embodiment, Ri represents a linear or branched, saturated or unsaturated, cyclic hydrocarbon chain such as cyclohexyl or cyclopentyl, or an acyclic C1-C6 chain, more preferably C1-C4, in particular Cp

[0221] Preferably, Ri represents a linear or branched, preferably linear, saturated or unsaturated, acyclic hydrocarbon chain, in Ci-Ci0, preferably in Ci-C6, more preferably in Ci-C4, in particular in Cp

[0222] Preferably, Ri represents a linear, saturated or unsaturated, acyclic hydrocarbon chain in Ci-Ci0, preferably in Ci-C6, more preferably in CrC4, in particular in Cp

[0223] Preferably, Ri represents a linear, saturated or unsaturated, acyclic alkyl chain in CrC4, in particular in Cp

[0224] Preferably, X represents a divalent radical -C(O)- or CH(OH)-.

[0225] Advantageously, in formula (I): - X represents a divalent radical -C(O)- or -CH(OH)-, - SA' represents a monosaccharide group selected from the group consisting of D-glucose, D-galactose, D-mannose, D-xylose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine, preferably selected from D-glucose, D-galactose, D-mannose, D-xylose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, more preferably selected from D-glucose, D-xylose or L-fucose; - Ri represents a linear, saturated or unsaturated, acyclic hydrocarbon chain, in Ci-Ci0, preferably in Ci-C6, more preferably in CrC4, in particular a methyl group.

[0226] According to one embodiment, in formula (III), Ri and R2 are identical, and represent a linear or branched, saturated or unsaturated, cyclic or acyclic, preferably acyclic, hydrocarbon chain in Ci-C6, more preferably in CrC4, in particular in Cp

[0227] Preferably, in formula (III), Ri and R2 are identical, and represent a linear or branched, saturated or unsaturated, acyclic hydrocarbon chain, in Ci-C6, more preferably in CrC4, in particular in Cp

[0228] Preferably, in formula (III), Ri and R2 are identical, and represent a linear, saturated or unsaturated, acyclic hydrocarbon chain in CrC4, in particular in Cp

[0229] According to one embodiment, in formula (IV), R2 represents a linear or branched, saturated or unsaturated, cyclic or acyclic hydrocarbon chain, preferably acyclic, in C1-C6, more preferentially in C1-C4, particularly in Cp

[0230] Preferably, in formula (IV), R2 represents a linear or branched, saturated or unsaturated, acyclic hydrocarbon chain, in C1-C6, more preferably in C1-C4, in particular in Cp

[0231] Preferably, in formula (IV), R2 represents a linear, saturated or unsaturated, acyclic hydrocarbon chain in CrC4, in particular in Cp

[0232] Preferably, in formulas (I), (III) and (IV), Ri and R2 are identical, and represent a linear, saturated or unsaturated, acyclic hydrocarbon chain in CrC10, preferably in CrC4, in particular in Cp

[0233] According to one embodiment, D may be an organic cation, preferably chosen from the group consisting of ammonium, phosphonium, imadazolium, pyrazolium, piperidinium, and piperazinium ions.

[0234] According to one embodiment, D is an inorganic cation chosen from the group consisting of alkali metal cations, alkaline earth metal cations.

[0235] Advantageously, D is a cation chosen from the group consisting of alkali metal cations, alkaline earth metal cations, the ammonium ion (NH4+), in particular alkali metal cations, alkaline earth metal cations.

[0236] Preferably, D is a cation selected from the group consisting of the calcium ion (Ca2+), the magnesium ion (Mg2+), the sodium ion (Na+) and the potassium ion (K+), in particular the calcium ion and the sodium ion, more particularly the sodium ion.

[0237] Advantageously, SA' corresponds to the following formula (II'): OH (HO)?

[0238] Formula (II') wherein the index n is equal to 0 or 1, preferably equal to 1, and the index p is an integer ranging from 1 to 4, preferably the index p is equal to 3.

[0239] Preferably, in formula (II'), n is equal to 1 and p is an integer ranging from 1 to 4, preferably the index p is equal to 3.

[0240] More preferably, in formula (II'), n is equal to 1 and p is equal to 3.

[0241] The process for preparing at least one compound of formula (I) is preferably a process for preparing at least one compound of the following formula (I'):

[0242] Formula (!') in which: - n is equal to 0 or 1, preferably is equal to 1, - p is an integer ranging from 1 to 4, preferably the index p is equal to 3, - RI has the same meaning as in formula (I), preferably re presents a linear hydrocarbon chain, preferably acyclic, in CrC io, preferably in Ci-C6, more preferably in Ci-C4, in particular in ci; - X represents a divalent radical -C(O)- or -CH(OR)-, - R represents a hydrogen atom, an alkyl group in CrCl₂, of preferably in Ci-C4, such as methyl, or an alkyl(CrC4)carbonyl group such as acetyl; preferably R represents a hydrogen atom,

[0243] as well as one of its optical isomers, geometric isomers, and / or one of its solvates such as hydrates;

[0244] said process comprising: - at least one reaction step (i) proceeding according to the following synthesis scheme (A'): synthesis route (A') in which: • n is equal to 0 or 1, preferably is equal to 1, • p is an integer ranging from 1 to 4, preferably the index p is equal to 3 • Ri and R2 are identical or different, preferably identical; with R2 having the same meaning as Ri in the formula (!'), • D+ is an organic or inorganic cation, preferably inorganic, more preferentially chosen from the group consisting of alkali metal cations, alkaline earth metal cations and ammonium (NH4+); better from the group consisting of alkali metal cations, alkaline earth metal cations;

[0245] said reaction step (i) being carried out in an aqueous medium in the presence of: • of at least one compound of formula (II'), • of at least one compound of formula (III), preferably present in a equimolar quantity or in excess with respect to the compound of formula (II'), preferably in excess, • preferably, the molar ratio of compound(s) of formula (III) / compound(s) of formula (II') is greater than or equal to 1, preferably between 1 and 5, more preferably between 1 and 4, even more particularly between 1 and 3, better between 1 and 2, in particular ranging from 1 to 1.5; according to a particular embodiment, the molar ratio of compound(s) of formula (III) / compound(s) of formula (II') is greater than 1, • of at least one alkali agent in an equimolar quantity or in excess, preferably in excess, relative to the compound of formula (II'), • preferably, the molar ratio of alkali agent(s) / compound(s) of formula (II') is greater than or equal to 1, preferably between 1 and 5, more preferably between 1 and 4, even more particularly between 1 and 3, better between 1 and 2; according to a particular embodiment, the molar ratio of alkali agent / compound of formula (II') is greater than 1, • the alkali agent being preferably mineral, more preferably chosen from the group consisting of alkali or alkaline earth metal hydroxides, alkali or alkaline earth metal (bi)carbonates, and mixtures thereof; in particular alkali or alkaline earth metal hydroxides, such as sodium hydroxide,

[0246] to lead to the formation of at least one compound of formula (l'Ai), and at least one compound of formula (IV);

[0247] - optionally, at least one reaction step (ii) of at least of said compound formula (l'Ai) to lead to at least one compound corresponding to the formula (l'Bl): WW Formula (lBl) in which the indices n, p and RI have the same meanings as in formula (I); • Preferably, reaction step (ii) is a reduction step (iil), as defined previously, • at least one purification (P) of the reaction medium including at least said compound of formula (IV), prepared in an aqueous medium, comprising successively: • at least one processing step (PI) implemented with at least one cationic ion exchange resin to convert at least said compound of formula (IV) into a compound of formula (IV') according to the following scheme: OO 1. — 1 0' S Rj-" 'OH * W said treatment step (PI) being carried out at a pH strictly lower than the pKa of the compound of formula (IV') or lower than the lowest pKa of the compounds of formula (IV') if several are present, • at least one separation step (P2) of at least of said compound of formula (IV') from the reaction medium.

[0248] The reaction step (i) and the purification step (P) are as defined previously.

[0249] Preferably, the purification (P) is carried out after the reaction step (i).

[0250] Preferably, the purification (P) is carried out at least between the step of reaction (i) and at least one reaction step (ii), and / or at least after at least one reaction step (ii), for example after one and / or two reaction steps (ii).

[0251] Preferably, the reaction step (ii) is a reduction step (iil) taking place in aqueous medium according to the following synthesis route (Bl): (ISP) (FBI) synthetic route (Bl) in which: - the index p and Ri have the same meaning as in formula (I).

[0252] Preferably, the reduction step (iil) is a reduction by catalytic hydrogenation, as defined above.

[0253] For the purposes of the present invention, a compound of formula (l'Ai) is a compound of formula (I') in which X corresponds to a divalent radical -C(O)-.

[0254] For the purposes of the present invention, a compound of formula (l'B 1) is a compound of formula (!') in which X corresponds to a divalent radical -CH(OH)-.

[0255] Preferably, the purification (P) is carried out at least between the reaction step (i), as described above, and the reduction step (iil), as described above.

[0256] More preferably, the process for preparing at least one compound of formula (I) is a process for preparing at least one compound of the following formula (I”): OH as well as one of its optical isomers, geometric isomers, and / or one of its solvates such as hydrates;

[0257] said process comprising: - at least one reaction step (i) proceeding according to the following synthesis scheme (A”): (n,!) (III) (TV") synthesis route (A”) in which: • D+ is a cation chosen from the group consisting of alkali metal cations, alkaline earth metal cations and ammonium (NH4+);

[0258] said reaction step (i) being carried out in an aqueous medium, in the presence of: • of at least one compound of formula (III'), preferably present in an equimolar quantity or in excess with respect to the compound of formula (II”), • preferably, the molar ratio of compound(s) of formula (III) / compound(s) of formula (II”) is greater than or equal to 1, preferably between 1 and 5, more preferably between 1 and 4, even more particularly between 1 and 3, better between 1 and 2, in particular ranging from 1 to 1.5; according to a particular embodiment, the molar ratio of compound(s) of formula (III) / compound(s) of formula (II”) is greater than 1,

[0259] • of at least one alkali agent in an equimolar quantity or in excess, preferably in excess, relative to the compound of formula (II”), • preferably, the molar ratio of alkali agent(s) / compound(s) of formula (II') is greater than or equal to 1, preferably between 1 and 5, more preferably between 1 and 4, even more particularly between 1 and 3, better between 1 and 2; according to a particular embodiment, the molar ratio of alkali agent / compound of formula (II) is greater than 1, • the alkali agent being preferably mineral, more preferably chosen from the group consisting of alkali or alkaline earth metal hydroxides, in particular sodium hydroxide, to lead to the formation of at least one compound of formula (I”A) and at least one compound of formula (IV”); - optionally, at least one reaction step (ii) of at least one of said compound of formula (I”A), to give at least one compound corresponding to the following formula (I”B): OH (F T B) • Preferably, reaction step (ii) is a reduction step (iil), as defined previously, at least one purification (P) of the reaction medium including at least said compound of formula (IV”), carried out in aqueous medium, comprising successively: • at least one processing step (PI) implemented with at least one cationic ion exchange resin to convert at least said compound of formula (IV”) into a compound of formula (IV'”) according to the following scheme:

[0260] said treatment step (PI) being carried out at a pH strictly lower than the pKA of the compound of formula (IV'”) or lower than the lowest pKa of compounds of formula (IV”') if several are present, • at least one separation step of at least of said compound of formula (IV”') from the reaction medium.

[0261] The reaction step (i) and the purification step (ii) are as defined above.

[0262] Preferably, the purification (P) is carried out at least between the reaction step (i) and at least one reaction step (ii), and / or at least after at least one reaction step (ii), for example after one and / or two reaction steps (ii).

[0263] For the purposes of the present invention, a compound of formula (I” A) is a compound of formula (I”) in which X corresponds to a divalent radical -C(O)-.

[0264] For the purposes of the present invention, a compound of formula (I”B) is a compound of formula (I”) in which X corresponds to a divalent radical -CH(OH)-.

[0265] Preferably, the reaction step (ii) is a reduction step (iil) taking place in aqueous medium according to the following synthesis route (B”): (1 A)

[0266] Preferably, the reduction step (iil) a reduction by catalytic hydrogenation, as defined above.

[0267] Preferably, the purification (P) is carried out at least between the reaction step (i) and at least one reduction step (iil), and / or at least after at least one reduction step (iil), for example after one and / or two reaction steps (ii).

[0268] Preferably, a purification (P) is implemented at least between the reaction step (i) and the reduction step (iil).

[0269] The process for preparing at least one compound of formula (I') or (I”) may further include the additional steps described for the process for preparing at least one compound of formula (I). purification process

[0270] The present invention also relates to a method for purifying at least one aqueous medium comprising at least one compound conforming to formula (I), as defined above, and at least one compound of formula (IV), as defined above, comprising: • at least one processing step (PI) implemented with at least one cationic ion exchange resin to convert at least said compound of formula (IV) into a compound of formula (IV') according to the following scheme: sth ■ R / '"'" VOH (laughs)

[0271] said treatment step (PI) being carried out at a pH strictly lower than the pKa of the compound of formula (IV') or lower than the lowest pKa of the compounds of formula (IV') if several are present, and • at least one separation step (P2) of at least of said compound of formula (IV') from the reaction medium.

[0272] The processing step (PI) and the separation step (P2) are as defined previously.

[0273] For the purposes of this invention, aqueous medium means any aqueous medium free from any water-miscible organic solvent, as defined above, preferably an aqueous medium free from any organic solvent.

[0274] Thus the purification process is carried out in an aqueous medium, free from any water-miscible organic solvent, comprising at least one compound of formula (IV), that is to say an aqueous reaction medium not comprising any water-miscible organic solvent, preferably not comprising any organic solvent.

[0275] In other words, the treatment step (PI) and the separation step (P2) do not use any water-miscible organic solvent.

[0276] More specifically, the treatment step(s) (PI) and the separation step(s) do not use any water-miscible or water-immiscible organic solvent.

[0277] The invention is illustrated in more detail in the following non-limiting examples. Examples:

[0278] Example 1 - Preparation of CBD-xylopyranoside-2-hydroxypropane (47% in weight)

[0279] Step 1: Preparation of a compound of formula (I”)

[0280] Water (1.04 kg) is placed in a reactor at 20°C. The mixture is heated to 50°C, then D-xylose (700 g) is added and stirred until the mixture is homogeneous. The mixture is then cooled to 15°C and acetylacetone (555 g) is added. A 50% sodium hydroxide solution (540 g) is added at a temperature below 45°C. The mixture is then heated from 30 to 50°C for 30 minutes to 4 hours, then optionally cooled to 20°C and passed through a strong sulfonic ion exchange resin until the pH is between 2.5 and 3.5.

[0281] Several cycles of water addition and water distillation are then carried out until an acetic acid content of less than 10,000 ppm, or even less than or equal to 6,000 ppm, and a dry extract of 30% to 60% are obtained. The pH is then adjusted to 6.0-7.0.

[0282] The product is isolated in solution with a yield of 90-95%.

[0283] Step 2: Catalytic hydrogenation to obtain the compound of formula (1'1) .O. > rv”

[0284] The compound of formula (!') (2.08 kg) in aqueous solution with the appropriate acetic acid content is introduced into a hydrogenator with ruthenium on carbon (catalytic quantity). The mixture is purged at least once with nitrogen and then with hydrogen. The mixture may be heated to a temperature above 25°C, and then hydrogen is introduced under pressure up to a pressure of approximately 10 bar.

[0285] The mixture is heated to a temperature of 100°C or less for a period of 2 to 7 hours under a pressure of 8 to 12 bars.

[0286] The hydrogenation reaction is carried out until the end of hydrogen consumption.

[0287] The reaction medium can be allowed to return to room temperature (20°C) and then optionally purged with an inert gas (nitrogen). The catalyst is then filtered, and the filtrate is then optionally contacted with carbon black. The solution is concentrated until a dry extract of 40 to 80% is obtained.

[0288] The pH of the filtrate is adjusted to acidic pH (for example between 4 and 6).

[0289] A glycol derivative such as a solvent may be added to the previous solution. propylene glycol to obtain a compound content of formula (I) of 20 to 90%.

[0290] The product is isolated in solution with a good yield (between 90-95%) and an acetic acid content of the solution of less than 20,000 ppm.

Claims

1. Claims Process for the preparation of at least one compound of the following formula (I): _ R-? (I) Formula (I) in which: - SA' represents a monosaccharide group or a polysaccharide group comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and / or furanose form and of L and / or D series, said monosaccharide group or polysaccharide group having at least one free substituted hydroxy group, and optionally at least one optionally protected amine group, - the bond between SA' and CH2-X is a C-anomeric bond, - X represents a divalent radical -C(O)- or -CH(OR)-, - R represents a hydrogen atom, an alkyl group in C1-C10, preferably C1-C4, such as methyl, or an alkyl(C1-C4)carbonyl group such as acetyl, preferably a hydrogen atom; - Ri represents a hydrocarbon chain, saturated or unsaturated, linear or branched, cyclic or acyclic, preferably acyclic, in C1-C10, preferably in C1-C4, more preferably saturated as well as one of its optical isomers, geometric isomers, and / or one of its solvates such as hydrates; said method comprising: - at least one reaction step (i) taking place according to the following synthesis scheme (A): synthesis route (A) in which: • Ri and R2 are the same or different; with R2 having the same meaning as Ri in formula (I), • SA' has the same meaning as in formula (I), • D+ is an organic or inorganic cation derived from the alkaline agent, preferably D+ is an inorganic cation; said reaction step (i) being carried out in aqueous media in the presence of: • at least one compound of formula (II), • at least one compound of formula (III), and • at least one alkaline agent in an equimolar or excess quantity relative to the compound of formula (II), preferably in excess, to lead to the formation of at least one compound of formula (IA) and at least one compound of formula (IV); - optionally, at least one reaction step (ii) of at least said compound of formula (IA), in a preferably aqueous medium, to lead to the formation of at least one compound corresponding to the following formula (IB): SA f GOLD. (IB) Formula (IB) in which SA', Ri and R have the same meanings as in formula (I); - at least one purification (P) of the reaction medium including at least said compound of formula (IV), carried out in an aqueous medium, comprising: • at least one treatment step (PI) carried out with at least one cationic ion exchange resin to convert at least said compound of formula (IV) into a compound of formula (IV') according to the following scheme: said treatment step (PI) being carried out at a pH strictly lower than the pKA of the compound of formula (IV') or lower than the lowest pKa of the compounds of formula (IV') if several are present, • at least one step of separation (P2) of at least said compound of formula (IV') from the reaction medium.

2. Process according to claim 1, characterized in that the reaction step (i) is carried out in an aqueous medium in the presence of: • at least one compound of formula (II), • at least one compound of formula (III), • preferably, the molar ratio compound(s) of formula (III) / compound(s) of formula (II) is greater than or equal to 1, preferably between 1 and 5, more preferably between 1 and 4, even more particularly between 1 and 3, better still between 1 and 2, in particular ranging from 1 to 1.5; in particular, the molar ratio compound(s) of formula (III) / compound(s) of formula (II) is greater than 1; of at least one mineral alkaline agent, preferably chosen from the group consisting of alkali or alkaline-earth metal hydroxides, alkali or alkaline-earth metal (bi)carbonates, and mixtures thereof; in particular alkali or alkaline-earth metal hydroxides, such as sodium hydroxide, • the alkaline agent being in an equimolar or excess quantity, preferably the molar ratio of alkaline agent(s) / compound(s) of formula (II) is greater than or equal to 1, preferably between 1 and 5, more preferably between 1 and 4, even more particularly between 1 and 3, better still between 1 and 2, • preferably, the reaction step (i) takes place: • at a temperature ranging from 20°C to 80°C, preferably at a temperature ranging from 20°C to 70°C, more preferably at a temperature ranging from 30°C to 70°C, better still from 30°C to 60°C, even better still at a temperature ranging from 35°C to 45°C; • preferably, the reaction time varies: • from 10 minutes to 10 hours, preferably from 20 minutes to 5 hours, more preferably from 30 minutes to 4 hours, even more preferably from 45 minutes to 3 hours.

3. Method according to claim 1 or 2, characterized in that the purification(s) (P) can be carried out at least once between a reaction step (i) and at least one reaction step (ii), and / or at least once after at least one reaction step (ii), preferably the purification (P) is carried out at least once at the end of the reaction step(s) (i).

4. Process according to any one of the preceding claims, the purification (P) is carried out in an aqueous reaction medium comprising at least said compound of formula (IV) and is free of any water-miscible organic solvent, preferably free of organic solvent chosen from the group consisting of dichloromethane, diethyl ether, ethanol, methanol, isopropanol, butanol, isobutanol, tert-butanol, toluene, isopropanol and mixtures thereof, more preferably free of any organic solvent.

5. Method according to any one of the preceding claims, characterized in that the treatment step(s) (PI) is or are carried out with at least one cationic resin having carboxylic groups and / or at least one sulfonic resin, preferably at least one sulfonic resin.

6. Method according to any one of the preceding claims, characterized in that the treatment step(s) (PI) is or are carried out at a pH ranging from 1.5 to 6, preferably ranging from 2 to 4.5, more preferably ranging from 2 to 3.5, better still in a pH range ranging from 2.5 to 3.

5.

7. Method according to any one of the preceding claims, characterized in that the separation step(s) (P2) is or are carried out by distillation, electrodialysis, preferably by vacuum distillation, more preferably by vacuum distillation at a temperature varying from 30°C to 80°C, preferably from 30°C to 55°C, preferably from 30°C to 50°C.

8. Process according to any one of the preceding claims, characterized in that, at the end of the separation step (P2), the content of compound(s) of formula (IV') is less than or equal to 10% by weight, preferably is less than or equal to 5% by weight, more preferably varies from 1 to 5% by weight, better still varies from 1 to 2% by weight, relative to the total weight of the dry extract containing the compound(s) of formula (I).

9. Process according to any one of the preceding claims, characterized in that the purification (P) comprises, simultaneously or sequentially, preferably sequentially, in particular before or after the treatment step (PI), more preferably before the treatment step (PI), at least one neutralization step (PO) of all or part of the excess alkaline agent present in the reaction medium resulting from step (i).

10. Process according to any one of the preceding claims, characterized in that the at least one purification step (P), carried out in an aqueous reaction medium, comprises: • at least one treatment step (PO) for neutralizing all or part of the excess alkaline agent present in the reaction medium resulting from the at least one step (i), • at least one treatment step (PI) of the reaction medium resulting from step (i) with at least one cationic ion exchange resin implemented at a pH value strictly lower than the pKa of the compound of formula (IV') or lower than the lowest pKa of the compounds of formula (IV'), • at least one separation step (P2) of at least said compound(s) of formula (IV') from the reaction medium, • at least one separation step (P'O) of the compound(s) of formula (III) present in the reaction medium at the end of the reaction(s) (i).

11. Process according to claim 9 or 10, characterized in that the neutralization step (PO) can be carried out with at least one cationic ion exchange resin at a pH value strictly lower than the pKa of the compound of formula (IV') or by adding at least one acidifying agent, organic or mineral, preferably mineral, in the reaction medium resulting from step (i).

12. Process according to any one of the preceding claims, characterized in that it further comprises at least one reduction step (ii) of at least said compound of formula (IA) to lead to at least one compound of formula (IB).

13. Process according to the preceding claim, characterized in that the reaction step (ii) is a reduction step (ii) taking place in an aqueous medium according to the following synthesis route (B): Reduction x'X SA”' IJ --------:----* SAr f ô to H (IA) (PB) synthesis route (B) in which: • SA' and RI have the same meanings as in formula (I).

14. Process according to claim 12 or 13, characterized in that the reaction step (ii) is at least one reduction step (iii) by catalytic hydrogenation, preferably carried out in the presence of at least one metal catalyst, more preferably ruthenium (Ru), nickel (Ni) or palladium (Pd).

15. Process according to any one of the preceding claims, characterized in that the compound of formula (I), in which X corresponds to a divalent radical -C(O)- or -CH(OR)-, is in solution in a liquid which comprises a content of at least 25% by weight of active material (I), preferably in a content ranging from 25 to 80% by weight, more preferably ranging from 25 to 75% by weight, more preferably ranging from 30 to 75% relative to the total weight of the solution.

16. Method according to any one of the preceding claims, characterized in that at least one step (iv) of adding at least one bactericidal or bacteriostatic agent, preferably bacteriostatic, preferably derived from glycol such as propylene glycol, pentylene glycol, caprylyl glycol.

17. Method according to any one of the preceding claims, characterized in that SA' represents a monosaccharide group chosen from the group consisting of glucose, in particular D-glucose, xylose, in particular D-xylose, fucose, in particular L-fucose, arabinoqe, in particular L-arabinose, rhamnose, in particular L-rhamnose, glucuronic acid, in particular D-glucuronic acid, galacturonic acid, in particular D-galacturonic acid, iduronic acid, in particular D-iduronic acid, N-acetyl glucosamine, in particular N-acetyl-D-glucosamine, N-acetyl-galactosamine, in particular N-acetyl-D-galactosamine, and preferably SA is chosen from D-glucose, D-xylose, L-fucose, L-arabinose, L-rhamnose, acid D-glucuronic acid, D-galacturonic acid, D-iduronic acid.

18. Process according to any one of the preceding claims, characterized in that Ri represents a linear or branched, saturated or unsaturated, cyclic or acyclic hydrocarbon chain, C1-C10, preferably C1-C6, more preferably C1-C4, in particular C,

19. Process according to any one of the preceding claims, characterized in that R 1 and R 2 are identical and represent a linear, saturated or unsaturated, acyclic hydrocarbon chain, C 1 -C 6, more preferably C 1 -C 4, in particular C 1

20. Process according to any one of the preceding claims, characterized in that X represents a divalent radical -C(O)- or -CH(OH)-.

21. A method according to any one of the preceding claims, characterized in that D+ is a cation selected from the group consisting of alkali metal cations, alkaline earth metal cations, ammonium ion (NH4+), preferably alkali metal cations, alkaline earth metal cations, in particular from a group consisting of calcium ion (Ca2+), magnesium ion (Mg2+), sodium ion (Na+) and potassium ion (K+).

22. Process for purifying at least one aqueous medium including at least one compound corresponding to formula (I), as defined according to any one of claims 1, 17, 18 and 20, and at least one compound of formula (IV), as defined according to claim 1 or 21, successively comprising: - at least one treatment step (PI) carried out with at least one cationic ion exchange resin to convert at least said compound of formula (IV) into a compound of formula (IV') according to the following scheme: said treatment step (PI) being carried out at a pH strictly lower than the pKA of the compound of formula (IV') or lower than the lowest pKa of the compounds of formula (IV') if several are present, and - at least one step of separation (P2) of at least said compound of formula (IV') from the reaction medium.