Novel branched glycerol derivatives and coating agents

Abstract

To provide a novel branched glycerol derivative, a coating agent containing the branched glycerol derivative as an active ingredient and capable of coating a surface of a substrate for imparting antifogging, antifouling property or the like, a coating method of a substrate surface using the coating agent, and a synthesis intermediate compound of the branched glycerol derivative.SOLUTION: A novel branched glycerol derivative is characterized by being represented by the following formula (I). [Wherein, R1 to R3 independently represent a hydrocarbon group having 1 to 6 carbon atoms; R4 and R5 independently represents H or the like, X represents a linker group of n+1 valence, and n represents an integer of 1 or more and 6 or less.]SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a novel branched glycerol derivative, a coating agent containing the branched glycerol derivative as an active ingredient and capable of coating the surface of a substrate to impart anti-fogging properties, anti-fouling properties, etc. to the substrate, a method for coating the surface of a substrate using the coating agent, and a synthetic intermediate compound for the branched glycerol derivative. [Background technology]

[0002] Glass contains sodium carbonate to lower its melting point and calcium oxide to reduce its water solubility, but its main component is silica (SiO2). Silica coatings, which offer high hardness, beautiful luster, and excellent durability, are also attracting attention. So-called glass coatings are sometimes advertised as stain-resistant. However, while silica is partially siloxylated (Si-OH), the majority of the silica consists of a disilyl ether structure (Si-O-Si). Because the disilyl ether structure is hydrophobic, glass and silica coatings can become cloudy in the presence of water vapor exceeding the saturated water vapor pressure, and can become susceptible to the adhesion of lipophilic stains that are difficult to clean.

[0003] Therefore, a technology has been developed to impart antifouling properties to substrates such as exterior walls by coating them with a layer containing a photocatalyst such as titanium oxide. However, photocatalysts can also decompose the organic polymer binder, making it difficult to fix to the substrate. Furthermore, because titanium oxide is also used as a white pigment, coating glass or the like with a layer containing titanium oxide can result in a decrease in transparency.

[0004] Furthermore, for the purpose of preventing fogging and staining of glass and the like, an anti-fouling and anti-fogging treatment agent for glass containing a 2-methacryloyloxyethyl phosphorylcholine copolymer and a silicone surfactant (Patent Document 1), and an anti-fouling and anti-fogging treatment agent for glass containing a partially hydrolyzed silicate, silica particles, phosphoric acid, and the like (Patent Document 2) have been developed.

[0005] However, simply applying a formulation to a substrate has limitations on the durability of the effect. Therefore, for example, Patent Document 3 describes an invention in which an optical element is covalently coated with an anti-fogging functional film via a siloxane bond. However, while such an anti-fogging functional film may be durable due to the siloxane bond, it is composed of a (meth)acrylic polymer having a viscosity-average molecular weight of 100 or more and 100,000 or less. This invention is merely a coating technology using a (meth)acrylic polymer, and has problems such as affecting the thickness dimension of the substrate and the uniformity of the polymer molecular weight.

[0006] Meanwhile, the present inventors have developed a branched glycerol structure as a structure for improving the water solubility of compounds (Patent Document 4). [Prior art documents] [Patent documents]

[0007] [Patent Document 1] Japanese Patent Application Laid-Open No. 2006-104005 [Patent Document 2] Japanese Patent Publication No. 2020-97693 [Patent Document 3] Japanese Patent Application Laid-Open No. 2016-71338 [Patent Document 4] International Publication No. 2004 / 29018 Brochure Summary of the Invention [Problem to be solved by the invention]

[0008] As mentioned above, various preparations for anti-fogging and anti-fouling of glass and other substrates are known, but no preparations have been developed to date that are truly long-lasting and have minimal effect on the substrate. Therefore, an object of the present invention is to provide a novel branched glycerol derivative, a coating agent containing the branched glycerol derivative as an active ingredient and capable of coating the surface of a substrate to impart anti-fogging properties, anti-fouling properties, etc. to the substrate, a method for coating the surface of a substrate using the coating agent, and a synthetic intermediate compound for the branched glycerol derivative. [Means for solving the problem]

[0009] The present inventors have conducted extensive research to solve the above problems, and as a result have found that a compound having a branched glycerol structure and a trialkoxysilyl group linked via a linker group can be covalently bonded to a substrate having at least a polysiloxane layer on its surface, and can impart sustained anti-fogging and anti-fouling properties to the substrate, thereby completing the present invention. The present invention will now be described.

[0010] [1] A branched glycerol derivative represented by the following formula (I): [ka] [In the formula, R 1 ~R 3 each independently represents a hydrocarbon group having 1 to 6 carbon atoms, R 4 and R 5 are independently H, C 1-6 Alkoxy-methyl group, C 2-6 Alkenyl group, tri(C 1-6 alkyl)silyl group, or (Ar) p -methyl group (wherein Ar is optionally substituted C 6-10 aryl group, and p is an integer of 1 or more and 3 or less. 4 and R 5 combine to form C 1-6 may form an alkanediyl group, X represents an (n+1)-valent linker group; n is an integer of 1 to 6, When n is an integer of 2 or more, multiple R 4 and R 5 may be the same or different from each other.

[0011] [2] A coating agent comprising the branched glycerol derivative according to [1] above as an active ingredient. [3] The coating agent according to [2] above, further comprising water. [4] The coating agent according to [2] or [3] above, further comprising an acid catalyst. [5] The coating agent according to the above [3], wherein the concentration of the branched glycerol derivative represented by the above formula (I) is 0.01 mol / L or more and 1 mol / L or less. [6] The coating agent according to any one of the above [2] to [5], further comprising a surfactant.

[0012] [7] A method for coating a surface of a substrate, comprising: A method comprising a step of treating the surface of a substrate with the coating agent according to any one of the above items [2] to [6]. [8] The method according to the above [7], wherein the surface of the substrate is treated by immersing the substrate in the liquid coating agent, or by applying or spraying the liquid coating agent onto the surface of the substrate. [9] The method according to [7] or [8] above, wherein the substrate is made of glass.

[0013]

[10] A branched glycerol derivative represented by the following formula (II): [ka] [In the formula, R 6 and R 7 are independently H, C 1-6 Alkoxy-methyl group, C 2-6 Alkenyl group, tri(C 1-6 alkyl)silyl group, or (Ar) q -methyl group (wherein Ar is optionally substituted C6-10 aryl group, and q is an integer of 1 or more and 3 or less, or R 6 and R 7 combine to form C 1-6 may form an alkanediyl group, Y represents an isocyanate group, an isothiocyanate group, an oxyamino group, an epoxy group, a vinyl group, a halogeno group, or a hydrazino group; Z represents an (m+1)-valent linker group; m is an integer of 1 to 6, When m is an integer of 2 or more, multiple R 6 and R 7 may be the same or different from each other. [Effects of the Invention]

[0014] The coating agent of the present invention can be covalently bonded to a substrate having at least a polysiloxane layer on its surface, and has excellent durability. Furthermore, the coating agent of the present invention can impart anti-fogging and anti-fouling properties to the substrate. Therefore, the coating agent of the present invention is industrially very useful as it can effectively improve the surface properties of the substrate. [Brief explanation of the drawings]

[0015] [Figure 1] FIG. 1 is a photograph of a glass sample that has been coated with the coating agent of the present invention and then exposed to steam. DETAILED DESCRIPTION OF THE INVENTION

[0016] The coating agent according to the present invention contains, as an active ingredient, a branched glycerol derivative represented by the following formula (I): Hereinafter, this compound will be abbreviated as "branched glycerol derivative (I)."

[0017] [ka]

[0018] In formula (I), R1 ~R 3 are independently hydrocarbon groups having 1 to 6 carbon atoms. Examples of hydrocarbon groups include C 1-6 Alkyl group, C 2-6 Alkenyl groups, and C 2-6 An alkynyl group is an example. If the number of carbon atoms is 6 or less, the water solubility of the branched glycerol derivative (I) can be more reliably ensured. The number of carbon atoms is preferably 4 or less, more preferably 1 or 2.

[0019] "C 1-6 The term "alkyl group" refers to a linear or branched monovalent saturated aliphatic hydrocarbon group having 1 to 6 carbon atoms. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, and n-hexyl. Preferably, C 1-4 alkyl group, more preferably C 1-2 It is an alkyl group, even more preferably methyl or ethyl.

[0020] "C 2-6 The term "alkenyl group" refers to a straight-chain or branched-chain monovalent unsaturated aliphatic hydrocarbon group having 2 to 6 carbon atoms and at least one carbon-carbon double bond. Examples include ethenyl (vinyl), 1-propenyl, 2-propenyl (allyl), isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, pentenyl, hexenyl, etc. Preferably, C 2-4 It is an alkenyl group, more preferably ethenyl (vinyl) or 2-propenyl (allyl).

[0021] "C 2-6 The term "alkynyl group" refers to a straight-chain or branched-chain monovalent unsaturated aliphatic hydrocarbon group having 2 to 6 carbon atoms and at least one carbon-carbon triple bond. Examples include ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, pentynyl, and hexynyl. Preferably, C 2-4 Alkynyl groups, more preferably C 2-3 It is an alkynyl group.

[0022] R 1 ~R 3 can be appropriately selected based on, for example, the hydrolysis rate of the trialkoxysilyl group. Generally, the hydrolysis rate of a metal alkoxide is faster for lower alkoxides, and is faster when the alkyl group is branched or the steric hindrance is large. Specifically, the hydrolysis rate of a metal alkoxide having a tertiary alkyl group is faster, and the hydrolysis rate of a metal alkoxide having a primary alkyl group is slower. Therefore, based on the desired reactivity of the branched glycerol derivative (I) according to the present invention, R 1 ~R 3 You can select:

[0023] In formula (I), R 4 and R 5 are independently H, C 1-6 Alkoxy-methyl group, C 2-6 Alkenyl group, tri(C 1-6 alkyl)silyl group, or (Ar) p -methyl group (wherein Ar is optionally substituted C 6-10 aryl group, and p is an integer of 1 or more and 3 or less. 4 and R 5 combine to form C 1-6 When n is an integer of 2 or more, a plurality of R 4 and R 5 may be the same or different. R other than H 4 and R 5 is a protecting group for a hydroxyl group, which can be easily removed with an acid.

[0024] "C 1-6 The term "alkoxy group" refers to a linear or branched saturated aliphatic hydrocarbon oxy group having 1 to 6 carbon atoms. Examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, n-pentoxy, n-hexoxy, etc., and preferably C 1-4 is an alkoxy group, more preferably C 1-2It is an alkoxy group, and even more preferably methoxy.

[0025] C 1-6 Alkoxy-methyl groups include, for example, methoxymethyl and ethoxymethyl.

[0026] "C 2-6 The term "alkenyl group" refers to a straight-chain or branched-chain monovalent unsaturated aliphatic hydrocarbon group having 2 to 6 carbon atoms and at least one carbon-carbon double bond. Examples include ethenyl (vinyl), 1-propenyl, 2-propenyl (allyl), isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, pentenyl, hexenyl, etc. Preferably, the alkenyl group is easily deprotected, such as -CH2-CH=CH-R 10 (In the formula, R 10 is H or C 1-3 It represents an alkyl group.) is preferred, and 2-propenyl (allyl) is more preferred.

[0027] (Ar) p In the -methyl group, p is preferably 2 or 3, more preferably 3, from the viewpoint of ease of deprotection. 6-10 Aryl groups include phenyl, indenyl, and naphthyl, with phenyl being preferred. 6-10 Examples of the substituent that the aryl group may have include C 1-6 The halogen atom may be substituted with one or more substituents selected from an alkoxy group, a halogen atom, a cyano group, and a nitro group. Examples of the halogen atom include fluoro, chloro, bromo, and iodo. Chloro or bromo is preferred, and chloro is more preferred. (Ar) p Examples of the -methyl group include monoarylmethyl groups such as benzyl, p-methoxybenzyl, 3,4-dimethoxybenzyl, o-nitrobenzyl, p-nitrobenzyl, p-halobenzyl, and p-cyanobenzyl; diarylmethyl groups such as diphenylmethyl; and triarylmethyl groups such as triphenylmethyl, α-naphthalenediphenylmethyl, p-methoxyphenyldiphenylmethyl, di(p-methoxyphenyl)phenylmethyl, and tri(p-methoxyphenyl)methyl.

[0028] Tori (C 1-6 Examples of the alkyl)silyl group include trimethylsilyl, triethylsilyl, triisopropylsilyl, dimethylisopropylsilyl, diethylisopropylsilyl, dimethylthexylsilyl, and t-butyldimethylsilyl.

[0029] "When n is an integer of 2 or more, multiple R 4 and R 5 may be the same or different from each other” means that when n is an integer of 2 or more and there are two or more branched glycerol structures in the square brackets of formula (I), multiple R 4 and multiple R 5 may be the same or different. 4 and R 5 Of course, they may be the same or different from each other.

[0030] R 4 and R 5 combine to form C 1-6 When forming an alkanediyl group, the branched glycerol structure in the square brackets of formula (I) has a structure represented by the following formula (III).

[0031] [ka]

[0032] In formula (III), R 8 and R 9 are independently H or C 1-6 The protecting group for the 1,3-diol group is relatively easy to remove.

[0033] In formula (III), R 8 and R 9 is H on one side and C on the other side. 1-6 Preferably, R is an alkyl group. 8 and R 9 Both are C1-6 The alkyl group can be removed under the mildest conditions, and as a result, it is possible to remove the protecting group without affecting the linker group, etc. 8 and R 9 The cyclic protecting group where both R and R are H is the most difficult to deprotect. 8 and R 9 One of them is H and the other is C 1-6 The ease of deprotection of a cyclic protecting group that is an alkyl group is intermediate between the above protecting groups.

[0034] In formula (I), X represents an (n+1)-valent linker group that connects n branched glycerol structures with a trialkoxysilyl group, and has the effect of facilitating the synthesis of the branched glycerol derivative (I) and increasing the positional freedom of the branched glycerol structure. The linker group is not particularly limited as long as it exhibits such an effect, but examples thereof include C 1-6 Alkanediyl group, optionally substituted C 1-6Alkanetriyl group, ether group (-O-), thioether group (-S-), amino group (>N- or -NH-), carbonyl group (-C(=O)-), thiocarbonyl group (-C(=S)-), ester group (-OC(=O)- or -C(=O)-O-), thioester group (-SC(=O)- or -C(=O)-S-), thionoester group (-OC(=S)- or -C(=S)-O-), amide group (- Examples of the linked group include NH-C(=O)- or -C(=O)-NH-), a thioamide group (-NH-C(=S)- or -C(=S)-NH-), a urea group (-NH-C(=O)-NH-), a thiourea group (-NH-C(=S)-NH-), an iminoether group (-C=NO- or -ON=C-), a polyalkylene glycol group, and a polyvinyl alcohol group; and groups in which two or more and five or less of these groups are linked together. Examples of the linked group include an ether group, a thioether group, an amino group, a carbonyl group, a thiocarbonyl group, an ester group, a thioester group, a thionoester group, an amide group, a thioamide group, a urea group, a thiourea group, an iminoether group, a polyalkylene glycol group, and a polyvinyl alcohol group at one end, both ends, and / or the middle, and which may have a substituent. 1-6 C having at one or more and three or less terminal and / or intermediate positions a group selected from the group consisting of an alkanediyl group, an ether group, a thioether group, an amino group, a carbonyl group, a thiocarbonyl group, an ester group, a thioester group, a thionoester group, an amide group, a thioamide group, a urea group, a thiourea group, an iminoether group, a polyalkylene glycol group, and a polyvinyl alcohol group, and which may have a substituent. 1-6 An example is an alkanetriyl group.

[0035] C 1-6 Alkanediyl groups and C 1-6 Examples of the substituent that the alkanetriyl group may have include a hydroxyl group, C 1-6The number of substituents is not particularly limited as long as it is substitutable, but may be, for example, 1 to 5, preferably 3 or less, more preferably 2 or less, and even more preferably 1.

[0036] The branched glycerol derivative (I) may contain a dendrimer structure in which two or more branched glycerol units are linked by a glycerol structure. Examples of such dendrimer structures include the following: The left side is a dendrimer structure in which n=2 and X is a trivalent linker group, and the right side is a dendrimer structure in which n=4 and X is a pentavalent linker group.

[0037] [ka]

[0038] In formula (I), the structure in parentheses may be referred to as a "branched glycerol unit." In formula (I), n represents the number of branched glycerol units and is an integer of 1 to 5. When n is 1 or more, the hydrophilicity of the branched glycerol derivative (I) can be ensured, and when n is 5 or less, the production cost of the branched glycerol derivative (I) can be effectively reduced. n is preferably 2 or more, and is preferably 4 or less, with 2 being more preferred.

[0039] The branched glycerol derivative (I) has a relatively simple structure and can be easily synthesized by a person skilled in the art. For example, the branched glycerol derivative (I) can be produced by reacting the branched glycerol derivative (II) with a trialkoxysilane compound.

[0040] [ka]

[0041] In formula (II), R 6 and R 7 are independently H, C1-6 Alkoxy-methyl group, C 2-6 Alkenyl group, tri(C 1-6 alkyl)silyl group, or (Ar) q -methyl group (wherein Ar is optionally substituted C 6-10 aryl group, and q is an integer of 1 or more and 3 or less, or R 6 and R 7 combine to form C 1-6 an alkanediyl group may be formed, Y represents an isocyanate group, an isothiocyanate group, an oxyamino group, an epoxy group, a vinyl group, a halogeno group, or a hydrazino group, Z represents an (m+1)-valent linker group, m represents an integer of 1 or more and 6 or less, and when m is an integer of 2 or more, a plurality of R 6 and R 7 may be the same or different from each other.

[0042] In formula (II), R 6 and R 7 is R in formula (I) 4 and R 5 Z also represents a linker group similar to X in formula (I), but corresponds to the group of X other than the end of the trialkoxysilyl group that bonds the branched glycerol structure and the trialkoxysilyl group.

[0043] Those skilled in the art can select the branched glycerol derivative (II) and trialkoxysilane compound depending on the group that connects the branched glycerol structure and the trialkoxysilyl group in formula (I). For example, when the connecting group is a thioether group, the branched glycerol derivative (I) can be produced by the nucleophilic addition reaction of a thiol group to an epoxy group or by a thiol-ene reaction, as shown in the following reaction formula (where Z represents a linker group). However, in this case, R 4 and R 5 is preferably not H.

[0044] [ka]

[0045] The coating agent according to the present invention preferably contains water. Water is an effective component for promoting hydrolysis of trialkoxysilyl groups and deprotection of the branched glycerol structure. However, the coating agent according to the present invention may consist essentially of the branched glycerol derivative (I) alone and may be dissolved or dispersed in water before use.

[0046] From the viewpoint of solubility of the branched glycerol derivative (I), the coating agent according to the present invention may contain a water-miscible organic solvent in addition to water as a solvent. The water-miscible organic solvent refers to an organic solvent that can be mixed with water without limit. Examples of the water-miscible organic solvent include C 10 solvents such as methanol, ethanol, and 2-propanol. 1-3 Examples of suitable solvents include alcohol solvents; amide-based solvents such as dimethylformamide and dimethylacetamide; and sulfoxide-based solvents such as dimethyl sulfoxide. When a mixed solvent of water and a water-miscible organic solvent is used as the solvent, the proportion of water in the mixed solvent is preferably 50% by mass or more, 60% by mass or more, or 70% by mass or more, more preferably 80% by mass or more or 90% by mass or more, and even more preferably 95% by mass or more or 98% by mass or more. The solvent for the coating agent according to the present invention is preferably substantially water alone. In this disclosure, the term "substantially only" means that no other components are intentionally added, except for unavoidable impurities or contaminants.

[0047] The concentration of the branched glycerol derivative (I) in the coating agent of the present invention containing a solvent can be 0.01 mol / L or more and 1 mol / L or less. A concentration of 0.01 mol / L or more allows the base material to be more reliably coated with branched glycerol. On the other hand, a concentration of 1 mol / L or less allows the branched glycerol derivative (I) to be effectively dissolved or dispersed in the solvent. The concentration is preferably 0.02 mol / L or more, more preferably 0.05 mol / L or more, and preferably 0.5 mol / L or less, more preferably 0.2 mol / L or less. Furthermore, from the viewpoint of transportation costs, a solid coating agent or a solution or dispersion of a relatively high concentration of the branched glycerol derivative (I) may be shipped as a product and dissolved, dispersed, or diluted at the time of use.

[0048] The coating agent according to the present invention may contain an acid catalyst. The acid catalyst, together with water, promotes hydrolysis of the trialkoxysilyl group and deprotection of the branched glycerol structure. Examples of the acid catalyst include hydrogen chloride, phosphoric acid, and nitric acid.

[0049] The concentration of the acid catalyst in the coating agent of the present invention may be adjusted as appropriate, for example, to 0.005% by mass or more and 1% by mass or less relative to the coating agent including the solvent. A concentration of 0.005% by mass or more can more reliably promote hydrolysis of trialkoxysilyl groups and deprotection of branched glycerol structures, while a concentration of 1% by mass or less can more reliably suppress residual acid.

[0050] The coating agent according to the present invention may contain a surfactant. The surfactant has the effect of increasing the solubility and dispersibility of the branched glycerol derivative (I), stabilizing the liquid coating agent, and promoting the penetration of the liquid coating agent into narrow spaces. Any of nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants can be used as the surfactant.

[0051] Examples of nonionic surfactants include polyoxyethylene alkylamines such as POE laurylamine, polyoxyethylene alkyl ethers such as POE lauryl ether and POE cetyl ether, glycerin fatty acid esters such as glyceryl monostearate, and sorbitan fatty acid esters such as sorbitan monolaurate. Note that "POE" is an abbreviation for polyoxyethylene.

[0052] Examples of anionic surfactants include alkyl sulfates such as sodium lauryl sulfate, potassium lauryl sulfate, ammonium lauryl sulfate, magnesium lauryl sulfate, monoethanolamine lauryl sulfate, sodium myristyl sulfate, sodium stearyl sulfate, and sodium oleyl sulfate; alkyl ether sulfates such as POE(2) sodium lauryl ether sulfate and POE(3) sodium myristyl ether sulfate; N-acyl methyl taurine salts such as potassium coconut oil fatty acid methyl taurate and sodium lauroyl methyl taurate; N-acyl glutamates such as coconut oil fatty acid acyl glutamic acid; N-acyl methyl alanine salts such as sodium lauroyl methyl alanine; N-acyl sarcosine salts such as sodium lauroyl sarcosine; acyl lactates such as sodium stearoyl lactylate; and fatty acid salts such as potassium coconut oil fatty acid, potassium laurate, and triethanolamine laurate. Note that "POE" is an abbreviation for polyoxyethylene, and the number in parentheses indicates the number of moles added.

[0053] Examples of cationic surfactants include alkyl quaternary ammonium salts such as lauryltrimethylammonium chloride, stearyltrimethylammonium bromide, and dicocoyldimethylammonium chloride, and amine salts such as dimethylstearylamine and stearic acid diethylaminoethylamide.

[0054] Examples of amphoteric surfactants include betaine.

[0055] The concentration of the surfactant in the coating agent of the present invention may be adjusted as appropriate, and may be, for example, 0.005% by mass or more and 5% by mass or less relative to the coating agent including the solvent.

[0056] By treating the surface of a substrate having at least a polysiloxane layer on its surface with the coating agent of the present invention, a deprotected branched glycerol structure can be covalently bonded to the polysiloxane layer. Substrates having at least a polysiloxane layer on their surface also include glass, which is primarily composed of polysiloxane. While the polysiloxane structure contains some hydrophilic siloxy groups (HO-Si-OH and Si-OH), the majority of the structure is composed of hydrophobic disilyl ethers (Si-O-Si). Therefore, when water vapor exceeding the saturated vapor pressure adheres to the polysiloxane layer, the water vapor likely aggregates into spherical particles due to interfacial tension, resulting in clouding. In contrast, coating a polysiloxane layer with the coating agent of the present invention reduces the interfacial tension of the water due to the deprotected branched glycerol structure, allowing the water to spread widely and thinly across the polysiloxane layer, preventing clouding. Furthermore, it is believed that lipophilic contaminants are less likely to adhere to the surface, and that any contaminants that do adhere are easily removed by rinsing with water.

[0057] Examples of the substrate having at least a polysiloxane layer on the surface thereof include glass and substrates whose surfaces are coated with a polysiloxane layer.

[0058] The conditions for treating the surface of a substrate with the coating agent of the present invention are not particularly limited. For example, the substrate may be immersed in a liquid coating agent, or the liquid coating agent may be applied or sprayed onto the surface of the substrate. The substrate is then preferably heated to dry the coating agent, hydrolyze the trialkoxysilyl groups to the polysiloxane structure of the substrate, and promote deprotection of the branched glycerol structure. The heating temperature can be, for example, 40°C or higher and 150°C or lower, and the heating time can be, for example, 10 minutes or higher and 50 hours or lower. This treatment is believed to impart anti-fogging and anti-fouling properties to the substrate surface by hydrolyzing the trialkoxysilyl groups of the branched glycerol derivative (I) and covalently bonding them to the polysiloxane of the substrate, and deprotecting the branched glycerol structure. Therefore, the surface of the substrate may then be washed and further dried to remove by-products, etc. [Example]

[0059] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to the following examples, and it is possible to carry out the invention by making appropriate modifications within the scope of the above and below-described aims, and all such modifications are included in the technical scope of the present invention.

[0060] Example 1 (1) Synthesis of (2S,5s)-2-methyl-5-(3-(((2R,5s)-2-methyl-1,3-dioxan-5-yl)oxy)-2-(oxiran-2-ylmethoxy)propoxy)-1,3-dioxane

[0061] [ka]

[0062] Compound 1 (877 mg, 3 mmol, see WO2020 / 255741) was suspended in 50 wt% aqueous sodium hydroxide (10 mL, 5 g, 125 mmol). Tetrabutylammonium bromide (193 mg, 0.6 mmol) was added to the resulting suspension. While stirring at 0 °C, epichlorohydrin (0.941 mL, 1.11 g, 12 mmol) was added. Ten minutes after the addition, the reaction mixture was immersed in a 35 °C oil bath and stirred for 4 hours. The resulting mixture was poured into water (20 mL), and dichloromethane (30 mL) was added for phase separation. The resulting organic phase was washed twice with water (10 mL) and once with saturated brine (10 mL). It was then dried over anhydrous magnesium sulfate and concentrated to obtain a crude product as a pale yellow oil. Thereafter, the residue was purified by silica gel column chromatography (eluent: ethyl acetate / acetone=4 / 1) to obtain the target compound 2 (780 mg, 2.23 mmol, yield: 74%) as an oil. FT-IR(neat):2990,2862,2783,2723,2663,1442,1407,1341,1282,1244,1154,1093,1051,987,952,896,858,822,806,759cm -1 1H NMR(CDCl3,500MHz): δ4.71(q,J=5.0Hz,2H,((-O-)2CH-CH3)2),4.22-4.12,(m,4H,four of (-CH(-CH2-)2)2),3.99(dd,J=3.0,12.0Hz,1H,one of epoxy-CH2-O-),3.86-3.78(m,5H,four of (-CH(-CH2-)2)2,-O-CH(-CH2-)2),3.73(dd,J=2.5,4.5Hz,2H×0.5(opposite body),-CH2-),3.71(dd,J=2 .5,4.5,2H×0.5(heterosexual body), -CH2-),3.68-3.63(m,2H-CH2-),3.66(ddd,J=5.5,6.5,10.5Hz,2H,two of -CH(-CH2-)2),3.60(dd,J=6.0,12.0Hz,1H,one of epoxy-CH2-O-),3.29-3.25(m,2H,(-O-CH(-CH2-)2),3.19-3.14(m,1H,[CH-epoxy]),2.78(dd,J=4.5,5.0Hz,1H,one of [CH2-epoxy]),2.63(dd,J=3.0,5.0Hz,1H,one of [CH2-epoxy]),1.33(d,J=5.0Hz,6H,((-O-)2CH-CH3)2) 13 C NMR (CDCl3, 125MHz): δ99.1(CH×2,((-O-)2CH-CH3)2),78.9(CH,-CH2-O-CH(-CH2-)2),71.5( CH2,epoxy-CH2-O-),71.3(CH,(-CH(-CH2-)2)2),71.3(CH,(-CH(-CH2-)2)2),68.7(CH2,one of (-CH(-CH2-)2)2),68.6(CH2×3,three of (-CH(-CH2-)2)2),68.4(CH2,one of -CH(-CH2-)2),68.4(CH2,-CH(-CH2-)2),51.0(CH,epoxy),44.4(CH2,epoxy),21.0(CH3×2,((-O-)2CH-CH3)2) HRMS (ESI-TOF) m / z calcd for C 16 H 28 NaO8[M+Na]+ 371.1682 found 371.1683

[0063] (2) Synthesis of 4,4-diethoxy-14-(((2R,5s)-2-methyl-1,3-dioxan-5-yl)oxy)-13-((((2S,5s)-2-methyl-1,3-dioxan-5-yl)oxy)methyl)-3,12-dioxa-8-thia-4-silatetradecan-10-ol

[0064] [ka]

[0065] Compound 2 (761 mg, 2.18 mmol) was added with tetrabutylammonium bromide (35 mg, 0.11 mmol) and (3-mercaptopropyl)triethoxysilane (625 mg, 2.62 mmol), and the mixture was stirred for 11 hours at 60° C. The mixture was then subjected to silica gel column chromatography (eluent: ethyl acetate / acetone = 10 / 1) to obtain target compound 3 (999 mg, 1.7 mmol, yield: 78%) as a slightly cloudy oil. FT-IR(neat):3481,2974,2924,2883,2784,2729,2661,1640,1455,1443 ,1408,1391,1363,1341,1282,1244,1154,1097,986,958,896,859,803cm -1 1H NMR(CDCl3,500MHz):δ4.72(q,J=5.0Hz,2H,((-O-)2CH-CH3)2),4.24-4.10(m,4H,four of (-CH(-CH2-)2)2),3.91-3.80(m,4H,four of (-CH(-CH2-)2)2),3.82(q,J=7.0Hz,6H,(CH3-CH2-O-)3Si-),3.75-3.58(m,8H,-CH2-CH(-OH)-CH2-,-CH(-OH)-CH2-O-,-CH2-O-CH(-CH2-)2,-CH2-O-CH(-CH2-)2),3.26-3.21(m,2H,(-O-CH(-CH2-)2)2),2.63(d,J=6.5Hz,2H,-S-CH2-CH-),2.57(t,J=7.0Hz,2H,-CH2-CH2-S-),2.04(br,s,1H,-CH2-CH(-OH)-CH2-),1.74-1.65(m,2H,-Si-CH2-CH2-CH2-),1.34(d,J=5.0Hz,6H,((-O-)2CH-CH3)2),1.22(t,J=7.0Hz,9H,(CH3-CH2-O-)3Si-),0.77-0.69(m,2H,-Si-CH2-CH2-) 13C NMR(CDCl3,125MHz):δ99.1(CH×2,((-O-)2CH-CH3)2),78.9(CH,-CH2-O-CH(-CH2-)2),73.8(CH2,-CH(-OH)-CH2-O-),71.3(CH,one of (-CH(-CH2-)2)2),71.2(CH,one of (-CH(-CH2-)2)2),69.9(CH,-CH2-CH(-OH)-CH2-),68.8(CH2,one of -CH(-CH2-)2),68.7(CH2,one of -CH(-CH2-)2),68.6(CH2,one of -CH(-CH2-)2),68.6(CH2,one of -CH(-CH2-)2),68.2(CH2,one of -CH(-CH2-)2),68.0(CH2,one of -CH(-CH2-)2),58.4(CH2×3,(CH3-CH2-O-)3Si-,35.8(CH2,one of -CH2-S-CH2-),35.0(CH2,one of -CH2-S-CH2-),23.2(CH2,-Si-CH2-CH2-CH2-),21.0(CH3,(-O-)2CH-CH3),21.0(CH3,(-O-)2CH-CH3),18.3(CH3×3,(CH3-CH2-O-)3Si-),9.9(CH2,Si-CH2-CH2-CH2-) HRMS(ESI-TOF) m / z calculation for C 25 H 50 NaO 11 SSi [M+Na] + 609.2741 found 609.2748

[0066] Example 2 (1) Synthesis of 5,5'-((2-(allyloxy)propane-1,3-diyl)bis(oxy))bis(2,2-dimethyl-1,3-dioxane)

[0067] [ka]

[0068] Ground potassium hydroxide (190 mg, 3.4 mmol) was added to compound 4 (641 mg, 2 mmol) and stirred at 160 °C for 2 minutes to form an amber, nearly homogeneous solution. The reaction mixture was allowed to return to room temperature, and allyl bromide (0.508 mL, 725 mg, 6 mmol) was added, followed by stirring at 70 °C for 1.5 hours. The resulting suspension was added to water (40 mL) while taking care to avoid heat generation. The mixture was extracted with ethyl acetate (40 mL) and washed twice with water and once with saturated aqueous sodium bicarbonate. The organic layer was concentrated to give a crude product (640 mg) as a pale yellow oil. The crude product was subjected to silica gel column chromatography (eluent: hexane / ethyl acetate = 1 / 1) to give the target compound 5 (585 mg, 1.62 mmol, yield: 81%) as an oil. FT-IR(neat):3076,2992,2939,2872,1646,1455,1425,1372,1333,1283,1250,1227,1199,1153,1096,1043,997,936,831,732cm -1 1 H NMR(CDCl3,400MHz):δ5.89(ddt,J=5.6,10.4,17.2Hz,1H,CH2=CH-CH2-),5.27(tdd,J=1.6,1.6,17.2Hz,1H,one of CH2=CH-),5.17(tdd,J=1.6,1.6,10.4Hz,1H,one of CH2=CH-),4.13(ddd,J=1.6,1.6,5.6Hz,2H,=CH-CH2-O-),4.00-3.92(m,4H,four of (-CH(-CH2-)2)2),3.75(dd,J=2.0,6.4Hz,2H,two of -CH(-CH2-)2),3.72(dd,J=2.0,6.4Hz,2H,two of -CH(-CH2-)2),3.66-3.52(m,5H,-CH(-CH2-)2),-O-CH(-CH2-)2),3.47(tt,J=4.4,5.2Hz,2H,(-O-CH(-CH2-)2)2),1.43(s,6H,six of ((-O-)2C(-CH3)2)2),1.40(s,6H,six of ((-O-)2C(-CH3)2)2) 13C NMR(CDCl3,125MHz):δ134.9(CH,CH2=CH-CH2-),116.9(CH2,CH2=CH-),98.0(C×2,((-O-)2C(-CH3)2)2),77.1(CH,-O-CH(-CH2-)2),71.4(CH2,=CH -CH2-O-),70.9(CH×2,(-O-CH(-CH2-)2)2),68.6(CH2×2,-CH(-CH2-)2),62.5(CH2×2,-CH(-CH2-)2),62.5(CH2×2,-CH(-CH2-)2),24.4(CH3×2,two of ((-O-)2C(-CH3)2)2),22.6(CH3×2,two of ((-O-)2C(-CH3)2)2) HRMS(ESI-TOF) m / z calculation for C 18 H 32 NaO7[M+Na] + 383.2046 found 383.2037

[0069] (2) Synthesis of 14-((2,2-dimethyl-1,3-dioxan-5-yl)oxy)-13-(((2,2-dimethyl-1,3-dioxan-5-yl)oxy)methyl)-4,4-diethoxy-3,12-dioxa-8-thia-4-silatetradecane

[0070] [ka]

[0071] To compound 5 (256 mg, 0.71 mmol), (3-mercaptopropyl)triethoxysilane (0.256 mL, 254 mg, 1.07 mmol) and AIBN (12 mg, 0.071 mmol) were added, and the mixture was stirred at 60° C. for 1 hour. The mixture was subjected to silica gel column chromatography (eluent: hexane / ethyl acetate=3 / 2) to obtain the target compound 6 (370 mg, 0.62 mmol, yield: 85%) as an oil. FT-IR(neat):2973,2925,2878,1455,1372,1334,1294,1250,1227,1199,1156,1102,1044,997,960,831,789,733cm -1 1 H NMR(CDCl3,400MHz):δ3.97(dd,J=4.4,11.6Hz,4H,four of (-CH(-CH2-)2)2),3.81(q,J=6.8Hz,6H,(CH3-CH2-O-)3Si-),3.73(dd,J=1.6,6.8Hz,2H,two of -CH(-CH2-)2),3.71(dd,J=1.6,6.8Hz,2H,two of -CH(-CH2-)2),3.65(t,J=6.4Hz,2H,-CH2-CH2-O-),3.61-3.50(m,5H,-CH(-CH2-)2),-O-CH(-CH2-)2),3.46(tt,J=4.4,6.4Hz,2H,(-O-CH(-CH2-)2)2),2.57(t,J=7.2Hz,2H,-S-CH2-CH2-CH2-O-),2.52(t,J=7.6Hz,2H,Si-CH2-CH2-CH2-S-),1.82(tt,J=6.4,7.2Hz,2H,-S-CH2-CH2-CH2-O-),1.75-1.63(m,2H,Si-CH2-CH2-CH2-S-),1.43(s,6H,six of ((-O-)2C(-CH3)2)2),1.40(s,6H,six of ((-O-)2C(-CH3)2)2),1.23(t,J=6.8Hz,9H,(CH3-CH2-O-)3Si-),0.77-0.69(m,2H,-Si-CH2-CH2-) 13C NMR(CDCl3,125MHz):δ98.1(C×2,((-O-)2C(-CH3)2)2),78.1(CH,-O-CH(-CH2-)2-),71.0(CH×2 ,(-CH(-CH2-O-)2C-)2),68.9(CH2,-CH2-CH2-O-),68.6(CH2×2,-CH(-CH2-)2),62.6(CH2×2,two of (-CH(-CH2-)2)2),62.6(CH2×2,two of (-CH(-CH2-)2)2),58.4(CH2,one of (CH3-CH2-O-)3Si-), 58.4 (CH2, one of (CH3-CH2-O-)3Si-),58.3(CH2,one of (CH3-CH2-O-)3Si-),35.1(CH2,-S-CH2-CH2-CH2-O-),29.9(CH2,Si-CH2-CH2-CH2-S-),28.5(CH2,-S-CH2-CH2-CH2-O-),24.5(CH3×2,two of ((-O-)2C(-CH3)2)2),23.2(CH2,Si-CH2-CH2-CH2-S-),22.6(CH3×2,two of ((-O-)2C(-CH3)2)2),18.3(CH3×3,(CH3-CH2-O-)3Si-),9.9(CH2,-Si-CH2-CH2-) HRMS(ESI-TOF) m / z calculation for C 27 H 54 NaO 10 SSi [M+Na] + 621.3105 found 621.3113

[0072] Example 3: Synthesis of 4,4-diethoxy-14-(((2R,5s)-2-methyl-1,3-dioxan-5-yl)oxy)-13-((((2S,5s)-2-methyl-1,3-dioxan-5-yl)oxy)methyl)-3,8-dioxa-12-thia-4-silatetradecan-10-ol

[0073] [ka]

[0074] Compound 7 (118 mg, 0.41 mmol) was dissolved in acetonitrile (0.41 mL, 320 mg, 7.8 mmol), and triethoxy(3-glycidyloxypropyl)silane (125 μL, 126 mg, 0.41 mmol) and tetrabutylammonium bromide (26 mg, 0.082 mmol) were added in this order, followed by stirring at 60 °C for 16 hours. The resulting mixture was concentrated, and the residue was subjected to silica gel column chromatography (eluent: ethyl acetate only) to obtain the target compound 8 (96 mg, 0.16 mmol, yield: 40%) as an oil. FT-IR(neat):3471,2974,2917,2866,2784,2729,2660,2360,1632,1442,1409,1368,1282,1244,1154,1088,985,955,896,858,810cm -1 1H NMR(CDCl3,500MHz):δ4.71(q,J=5.0Hz,2H,((-O-)2CH-CH3)2),4.23-4.11(m,4H,four of (-CH(-CH2-)2)2),4.00-3.91(m,1H,-CH2-CH(-OH)-CH2-),3.87-3.72(m,8H,four of (-CH(-CH2-)2)2,-S-CH(-CH2-)2),3.82(q,J=7.0Hz,6H,CH3-CH2-O-)3Si-),3.48(dd,J=4.5,9.5Hz,1H,one of -CH2-CH2-O-),3.46(dd,J=6.0,9.5Hz,1H,one of -CH2-CH2-O-),3.44(t,J=6.5Hz,2H,-O-CH2-CH(-OH)-),3.28-3.21(m,2H,(-O-CH(-CH2-)2)2),3.15(quint,J=6.0Hz,1H,-S-CH(-CH2-)2),2.87(dd,J=6.0,14.0Hz,1H,one of -CH(-OH)-CH2-S-),2.77(dd,J=7.5,14.0Hz,1H,one of -CH(-OH)-CH2-S-),1.74-1.65(m,2H,-Si-CH2-CH2-CH2-),1.34(d,J=5.0Hz,3H,(-O-)2CH-CH3),1.33(d,J=5.0Hz,3H,(-O-)2CH-CH3),1.22(t,J=7.0Hz,9H,(CH3-CH2-O-)3Si-),0.66-0.60(m,2H,-Si-CH2-CH2-) 13C NMR(CDCl3,125MHz):δ99.2(CH,one of ((-O-)2CH-CH3)2),99.2(CH,one of ((-O-)2CH-CH3)2),73.7(CH2,-CH2-CH2-O-),73.3(CH2,-O-CH2-CH(-OH)-),71.2(CH,one of (-O-CH(-CH2-)2)2),71.2(CH,one of (-O-CH(-CH2-)2)2),70.0(CH,-CH2-CH(-OH)-CH2-),69.7(CH2,one of -S-CH(-CH2-)2),69.6(CH2,one of -S-CH(-CH2-)2),68.7(CH2,one of -O-CH(-CH2-)2),68.7(CH2,one of -O-CH(-CH2-)2),68.2(CH2,one of -O-CH(-CH2-)2),68.1(CH2,one of -O-CH(-CH2-)2),58.4(CH2×3,(CH3-CH2-O-)3Si-),45.8(CH,-S-CH(-CH2-)2),35.9(CH2,-CH(-OH)-CH2-S-),22.9(CH2,-Si-CH2-CH2-CH2-),21.0(CH3,one of ((-O-)2CH-CH3)2),21.0(CH3,one of ((-O-)2CH-CH3)2),18.3(CH3×3,(CH3-CH2-O-)3Si-),6.5(CH2,-Si-CH2-CH2-) HRMS(ESI-TOF) m / z calculation for C 25 H 50 NaO 11 SSi [M+Na] + 609.2741 found 609.2749

[0075] Example 4 (1) Synthesis of 1-((1,3-bis(((2R,5s)-2-methyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)-3-((1,3-bis(((2S,5s)-2-methyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)propan-2-ol

[0076] [ka]

[0077] A mixture of compound 1 (26.3 g, 90 mmol), tetrabutylammonium bromide (1.45 g, 4.5 mmol), potassium hydroxide (3.79 g, 67.5 mmol), and toluene (22.5 mL, 18 g, 195 mmol) was stirred at 80°C, and after forming a homogeneous solution, the mixture was returned to room temperature. While stirring the solution, epichlorohydrin (1.76 mL, 2.08 g, 22.5 mmol) was added over 5 minutes in a water bath at approximately 10°C. The mixture was then stirred at room temperature for 2 hours and at 40°C for 24 hours. The resulting mixture was concentrated, and ethyl acetate (100 mL) was added. The mixture was filtered and then concentrated. Excess compound 1 was recovered by vacuum distillation, and then purified by silica gel column chromatography (eluent: dichloromethane / acetone = 3 / 2 to 1 / 2) to obtain the target compound 9 (6.3 g, 9.8 mmol, yield based on epichlorohydrin: 43%) as an oil. FT-IR(neat):3481,2991,2863,2783,2726,2661,1455,1442,1407,1342,1282,1243,1154,1092,1051,986,953,895,858,822,805,753,665cm -1 1 H NMR(CDCl3,500MHz):δ4.71(q,J=5.0Hz,4H,(((-O-)2CH-CH3)2)2),4.23-4.08(m,8H,eight of ((-CH(-CH2-)2)2)2),3.97-3.88(m,1H,HO-CH(-CH2-)2),3.87-3.52(m,22H,eight of ((-CH(-CH2-)2)2)2,(-CH(-CH2-)2)2,HO-CH(-CH2-)2,(-CH(-CH2-)2)2),3.30- 3.22(m,4H,((-CH(-CH2-)2)2)2),1.33(dd,J=5.0Hz,12H,(((-O-)2CH-CH3)2)2) 13C NMR(CDCl3,125MHz):δ99.0(CH×4,(((-O-)2CH-CH3)2)2),78.8(CH×2,(-CH(-CH2-)2)2),72.0(CH2×2,( HO-CH(-CH2-)2),71.1(CH×2,(-CH(-CH2-)2)2),71.1(CH×2,(-CH(-CH2-)2)2),69.6(CH,HO-CH(-CH2-)2 ),68.6(CH2×2,-CH(-CH2-)2),68.6(CH2×2,-CH(-CH2-)2),68.5(CH2×2,-CH(-CH2-)2),68.4(CH2×2,-CH (-CH2-)2),68.2(CH2×2,-CH(-CH2-)2),68.1(CH2×2,-CH(-CH2-)2),21.0(CH3×4,(((-O-)2CH-CH3)2)2) HRMS(ESI-TOF) m / z calculation for C 29 H 52 NaO 15 [M+Na] + 663.3204 found 663.3194

[0078] (2) Synthesis of 1-((1,3-bis(((2R,5s)-2-methyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)-3-((1,3-bis(((2S,5s)-2-methyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)propan-2-yl 4-methylbenzenesulfonate To a solution containing compound 9 (6.13 g, 9.56 mmol), 4-dimethylaminopyridine (1.17 g, 9.56 mmol), and pyridine (9.56 mL, 9.44 g, 119.34 mmol), p-toluenesulfonyl chloride (3.64 g, 19.12 mmol) was added over 5 min at 0 °C. After 10 min, the mixture was returned to room temperature and stirred for 24 h. The resulting mixture was added to water (40 mL) and extracted with ethyl acetate (60 mL). The extract was washed twice with water (50 mL), once with saturated aqueous sodium bicarbonate (50 mL), and once with saturated brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to give crude product 10 (6.1 g, 7.67 mmol, 80% yield) as an orange oil. During concentration, toluene (200 mL) was added to remove pyridine by azeotropy. The resulting crude product 10 was used directly in the next reaction.

[0079] (3) Synthesis of S-(1-((1,3-bis(((2R,5S)-2-methyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)-3-((1,3-bis(((2S,5s)-2-methyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)propan-2-yl) ethanethioate To a solution of the crude product 10 (6.03 g, 7.58 mmol) in acetonitrile (15 mL, 11.7 g, 285 mmol), S-potassium thioacetate (2.59 g, 22.7 mmol) was added and stirred at 80 °C for 22 h. Ethyl acetate (30 mL) was added to the resulting mixture, which was then filtered and concentrated. Water (40 mL) was added, and the mixture was extracted twice with dichloromethane (50 mL). The extract was washed twice with water (30 mL) and once with saturated brine (30 mL), dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to give a crude product (5.62 g) as a reddish-brown oil. The crude product was subjected to silica gel column chromatography (eluent: dichloromethane / acetone = 5 / 2 to 2 / 1) to give the target compound 11 (4.52 g, 6.46 mmol, yield: 85%) as a reddish-brown oil. FT-IR (neat):3601,3525,2990,2860,2782,2727,2661,1691,1441,1408,1339,1282,1243,1153,1089,1052,1023,985,951,894,858,821,810,721,634,584cm -1 1 H NMR(CDCl3,500MHz):δ4.70(q,J=5.0Hz,4H,(((-O-)2CH-CH3)2)2),4.20-4.11(m,8H,eight of ((-CH(-CH2-)2)2)2),3.86-3.59(m,15H,-S-CH(-CH2-)2,eight of ((-CH(-CH2-)2)2)2,-S-CH(-CH2-)2,(-CH(-CH2-)2)2),3.69(dd,J=5.0,10.0Hz,4H,four of (-CH(-CH2-)2)2),3.64(dd,J=5.0,10.0Hz,2H,two of (-CH(-CH2-)2)2),3.63(dd,J=5.0,10.0Hz,2H,two of (-CH(-CH2-)2)2),3.30-3.24(m,4H,((-CH(-CH2-)2)2)2),2.31(s,3H,CH3-C(=O)-S-),1.33(d,6H,J=5.0Hz,((-O-)2CH-CH3)2),1.33(d,6H,J=5.0Hz,((-O-)2CH-CH3)2) 13C NMR(CDCl3,125MHz):δ195.1(C,CH3-C(=O)-S-),99.1(CH×4,(((-O-)2CH-CH3)2)2),78.9(CH×2,(-CH(- CH2-)2)2),71.3(CH×4,((-CH(-CH2-)2)2)2),69.1(CH2×2,-S-CH(-CH2-)2),68.7(CH2×2,-CH(-CH2-)2) ,68.7(CH2×2,-CH(-CH2-)2),68.4(CH2×2,-CH(-CH2-)2),68.4(CH2×4,(-CH(-CH2-)2)2),68.3(CH2×2,- CH(-CH2-)2),44.3(CH,-S-CH(-CH2-)2),30.7(CH3,CH3-C(=O)-S-),21.1(CH3×4,(((-O-)2CH-CH3)2)2) HRMS(ESI-TOF) m / z calculation for C 31 H 54 NaO 15 S [M+Na] + 721.3081 found 721.3082

[0080] (4) Synthesis of 1-((1,3-bis(((2R,5s)-2-methyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)-3-((1,3-bis(((2S,5s)-2-methyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)propane-2-thiol To a solution of compound 11 (500 mg, 0.72 mmol) in methanol (1.43 mL, 1.13 g, 35.3 mmol), potassium carbonate (99 mg, 0.72 mmol) was added and stirred at room temperature for 4 hours. The resulting mixture was concentrated. Water (20 mL) was added to the resulting residue, and the mixture was extracted with methylene chloride (40 mL) and concentrated to give a crude product (430 mg) as a red-orange oil. The crude product was subjected to silica gel column chromatography (eluent: dichloromethane / acetone = 2 / 1) to give the target compound 12 (300 mg, 0.46 mmol, yield: 63%) as a red oil. FT-IR(neat):3585,3525,2980,2971,2861,2782,2726,2661,2551,1456,1442,1407,1342,1281,1244,1154,1090,1050,986,952,895,857,822,806cm -1 1 H NMR(CDCl3,500MHz):δ4.71(q,J=5.0Hz,4H,(((-O-)2CH-CH3)2)2),4.23-4.10(m,8H,eight of ((-CH(-CH2-)2)2)2),3.85-3.79(m,8H,eight of ((-CH(-CH2-)2)2)2),3.79-3.73(m,6H,HS-CH(-CH2-)2,(-CH(-CH2-)2)2),3.67(dd,4H,J=4.5,10.5Hz,four of (-CH(-CH2-)2)2),3.64(dd,4H,J=5.5,10.5Hz,four of (-CH(-CH2-)2)2),3.31-3.25(m,4H,((-CH(-CH2-)2)2)2),3.13(dquint,J=5.5,8.0Hz,1H,HS-CH(-CH2-)2),2.05(d,J=8.0Hz,1H,HS-CH(-CH2-)2),1.33(dd,J=5.0Hz,12H,(((-O-)2CH-CH3)2)2) 13C NMR(CDCl3,125MHz):δ99.1(CH×4,((-O-)2CH-CH3)2)2),78.8(CH×2,(-CH(-CH2-)2)2),72.1(CH2×2,HS-CH(-CH2-)2),71.3(CH×2,two of ((-CH(-CH2-)2)2)2),71.3((CH×2,two of ((-CH(-CH2-)2)2)2),68.7(CH2×2,(-CH(-CH2-)2),68.6(CH2×2,-CH(-CH2-)2),68.4(CH2×2,-CH(-CH2-)2),68.4(CH2×2,-CH(-CH 2-)2),68.4(CH2×2,(-CH(-CH2-)2)2),68.3(CH2×2,-CH(-CH2-)2),40.0(CH,HS-CH(-CH2-)2),21.1(CH3×4,(((-O-)2CH-CH3)2)2) HRMS(ESI-TOF) m / z calculation for C 31 H 54 NaO 15 S [M+Na] + 679.2975 found 679.2977

[0081] (5) Synthesis of 13-(((1,3-bis(((2R,5S)-2-methyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)methyl)-4,4-diethoxy-17-(((2S,5S)-2-methyl-1,3-dioxan-5-yl)oxy)-16-((((2S,5S)-2-methyl-1,3-dioxan-5-yl)oxy)methyl)-3,8,15-trioxa-12-thia-4-silaheptadecan-10-ol Compound 12 (100 mg, 0.15 mmol) was dissolved in acetonitrile (30 μL, 23.7 mg, 0.58 mmol), and triethoxy(3-glycidyloxypropyl)silane (50 μL, 50 mg, 0.18 mmol) and tetrabutylammonium bromide (2 mg, 0.0075 mmol) were added in that order, followed by stirring at 60 °C for 24 hours. The resulting mixture was subjected to silica gel column chromatography (eluent: hexane / acetone = 1 / 1) to obtain the target compound 13 (70 mg, 0.074 mmol, yield: 50%) as an oil. FT-IR (neat):3480,2975,2865,2783,2727,2660,1456,1442,1408,1342,1282,1244,1154,1089,987,953,895,858,821,806,757,668,667,585cm -1 1H NMR(CDCl3,500MHz):δ4.71(q,J=5.0Hz,4H,(((-O-)2CH-CH3)2)2),4.23-4.10(m,8H,eight of ((-CH(-CH2-)2)2)2),3.92-3.73(m,15H,eight of ((-CH(-CH2-)2)2)2,-S-CH(-CH2-)2,(-CH(-CH2-)2)2),-CH2-CH(-OH)-CH2-),3.82(q,J=7.0Hz,6H,CH3-CH2-O-)3Si-),3.73-3.61(m,8H,((-CH(-CH2-)2)2)2),3.48-3.39(m,4H,-CH2-CH2-O-,-O-CH2-CH(-OH)-),3.31-3.25(m,4H,((-CH(-CH2-)2)2)2),3.03(q,J=6.0Hz,1H,-S-CH(-CH2-)2),2.79(dd,J=5.0,14.0Hz,1H,one of -CH(-OH)-CH2-S-),2.65(dd,J=7.5,14.0Hz,1H,one of -CH(-OH)-CH2-S-),1.73-1.64(m,2H,-Si-CH2-CH2-CH2-),1.33(d,J=5.0Hz,12H,(((-O-)2CH-CH3)2)2),1.22(t,J=7.0Hz,9H,(CH3-CH2-O-)3Si-),0.66-0.60(m,2H,-Si-CH2-CH2-) 13C NMR(CDCl3,125MHz):δ99.1(CH×4,(((-O-)2CH-CH3)2)2),78.9(CH×2,(-CH(-CH2-)2)2),73.7(CH2,-CH2-CH2-O-),73.4(CH2,-O-CH2-CH(-OH)-),71.4(CH2,one of -S-CH(-CH2-)2),71.3(CH2,one of -S-CH(-CH2-)2),71.3(CH×3,three of ((-CH(-CH2-)2)2)2),71.3((CH,one of ((-CH(-CH2-)2)2)2),70.0(CH,-CH2-CH(-OH)-CH2-),68.7(CH2,one of (-CH(-CH2-)2),68.7(CH2×3,three of -CH(-CH2-)2),68.4(CH2×2,two of -CH(-CH2-)2),68.4(CH2×3,three of -CH(-CH2-)2),68.4(CH2×2,two of (-CH(-CH2-)2)2),68.3(CH2,one of -CH(-CH2-)2),58.4(CH2×3,(CH3-CH2-O-)3Si-),46.8(CH,-S-CH(-CH2-)2),36.0(CH2,-CH(-OH)-CH2-S-),23.0(CH2 ,-Si-CH2-CH2-CH2-),21.1(CH3×4,((-O-)2CH-CH3)2)2),18.3(CH3×3,(CH3-CH2-O-)3Si-),6.5(CH2,-Si-CH2-CH2-) HRMS(ESI-TOF) m / z calculation for C 41 H 78 NaO 19 SSi [M+Na] + 957.4525 found 957.4500

[0082] Example 5 (1) Synthesis of 1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-amine

[0083] [ka]

[0084] To a solution of compound 14 (235 mg, 0.68 mmol) in tetrahydrofuran (1.7 mL, 1.51 g, 20.9 mmol), triphenylphosphine (356 mg, 1.36 mmol) and water (18 μL, 0.001 mmol) were added in this order, and the mixture was stirred at 50° C. for 28 hours. The resulting mixture was concentrated, and the resulting residue was subjected to silica gel column chromatography (eluent: dichloromenthane / methanol = 4 / 1) to obtain the target compound 15 (177 mg, 0.55 mmol, yield: 81%) as an oil. FT-IR(KBr):3383,3323,2881,1594,1460,1375,1253,1200,1153,1117,1085,937,831,732,583,527,472cm -1 1 H NMR(CDCl3,500MHz):δ3.974(dd,J=4,12Hz,CH-CH2-O),3.77(dd,J=6.5,12Hz,CH-CH2-O),3.52(dd,J=4.5,9Hz,CH-C H2-O),3.44-3.41(m,2H,O-CH-CH2),3.40(dd,J=6.5,9Hz,CH-CH2-O),3.14(tquint,J=5,6Hz,1H,H2N-CH-CH2),1.43 and 1.41(s,12H,C-CH3) 13 C NMR(CDCl3,125MHz):δ98.3(C×2,OCO),71.1(CH2×4,CH-CH2-O),70.9(CH×2,O-CH-CH2),62.6(CH2×2,CH-CH2-O),51.9(CH,H2N-CH-CH2),24.12,24.09,23.19 and 23.16(CH3×4,C-CH3) HRMS(ESI-TOF) m / z calculation for C 15 H 30 NO6[M+H] + 320.2073 found 320.2068

[0085] (2) Synthesis of N-(1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-yl)-2-((1,3-dioxoisoindolin-2-yl)oxy)acetamide

[0086] [ka]

[0087] To a solution of compound 16 (50.9 mg, 0.29 mmol) in acetonitrile (3 mL), HOBt (57.9 mg, 0.38 mmol) and EDC·HCl (72.5 mg, 0.38 mmol) were added at 0°C, and the resulting suspension was stirred for 30 min. The temperature of the reaction mixture was slowly raised to 25°C over 30 min, and compound 15 (93 mg, 0.29 mmol) and triethylamine (121 μL, 0.87 mmol) were added. The reaction mixture was then stirred at 40°C for 24 h. The reaction mixture was poured into water (30 mL) and extracted three times with ethyl acetate (60 mL). The extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: methylene chloride / methanol = 3 / 1) to obtain the target compound 17 as a pale yellow gummy liquid (100 mg, 0.21 mmol, yield: 72%). FT-IR(neat):3285,2991,2941,2876,1796,1736,1665,1534,1453,1371,1338,1245,1190,1098,1038,989,929,825,738cm -1 1 H NMR(CDCl3,500MHz):δ5.96-5.89(m,1H),5.37-5.27(dd,J trans =17,1.0Hz,J cis=10.5Hz,2H),4.66(d,J=6.0Hz,2H),4.39(s,2H),4.30-4.26(m,1H),4.0(dd,J=11.5,3.5Hz,4H),3.81(dd,J=5.0Hz,4. 5Hz,4H),3.72-3.69(dd,J=9.5,4.0Hz,2H),3.59-3.56(dd,J=9.0,3.0Hz,2H),3.42(quint,J=3.5Hz,2H),1.44(s,12H) 13 C NMR(CDCl3,125MHz):δ168.46(C,C=O),157.91(C,C=O),131.62(CH×1),118.82(CH2×1),98.35(C×2),75.91(CH2×1),7 0.51(CH×2),66.69(CH2×1),66.43(CH2×2),62.75(CH2×2),61.88(CH2×2),48.33(CH×1),24.22(CH2×2),22.95(CH2×2) HRMS(ESI-TOF) m / z calculation for C 21 H 37 N2O 10 [M+H] + 477.2468 found 477.2468

[0088] (3) Synthesis of 2-(aminooxy)-N-(1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-yl)acetamide

[0089] [ka]

[0090] To a solution of compound 17 (67.2 mg, 0.14 mmol) in methanol (2 mL), formic acid (3 eq, 16 μL, 0.42 mmol) and Pd-C 10% (0.2 eq, 30.1 mg, 0.028 mmol) were slowly added. The resulting suspension was stirred for 5 h and then filtered through Celite. The filtrate was concentrated under reduced pressure to give the desired compound 18 (33.4 mg, 0.085 mmol, 60% yield) as a colorless gummy liquid. FT-IR(neat):3393,2918,1654,1536,1451,1375,1341,1251,1198,1079,825cm -1 1 H NMR(CD3OD,500MHz):δ4.21(quint,J=5.5Hz,1H),4.05(t,J=3.5Hz,2H),4.02(t,J=3.0H z,2H),4.0(s,2H),3.81-3.77(m,4H),3.69-3.61(m,4H),3.41(quint,J=4.5Hz,2H),1.42 and 1.39(s,12H) 13 C NMR (CD3OD, 125MHz): δ168.23(C,C=O),98.02(C×2),70.78(CH×2),66.52(CH2×2),61. 90(CH2×2),61.84(CH2×2),61.18(CH2×1),48.57(CH×1),24.03(CH3×2),21.06(CH3×2) HRMS(ESI-TOF) m / z calculation for C 17 H 32 N2O8Na [M+Na] + 415.2056,found 415.2080

[0091] (4) Synthesis of N-(1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-yl)-9,9-diethoxy-3,10-dioxa-4-aza-9-siladodec-4-enamide

[0092] [ka]

[0093] To a solution of compound 18 (117 mg, 0.30 mmol) in ethanol (0.6 mL, 474 mg, 10.07 mmol), 90% triethoxysilylbutyraldehyde (97 μL, 93 mg, 0.36 mmol) was added and stirred at 40 °C for 8 h. The mixture was concentrated, and the resulting residue was subjected to silica gel column chromatography (eluent: hexane / ethyl acetate = 1 / 5) to obtain the target compound 19 (96 mg, 0.16 mmol, yield: 53%) as a cloudy oil. NMR analysis revealed that the ratio of geometric isomers at the C=N double bond was 8:2, but it was unclear whether the cis or trans isomer was the major product. FT-IR(neat):3429,2973,2927,2880,2245,1680,1519,1455,1413,1373,1337,1284,1250,1227,1198,1156,1083,956,830,792,732cm -1 1H NMR(CDCl3,500MHz):δ7.15(t,J=6.0Hz,0.8H,-CH2-CH=N-O-),6.75(t,J=5.5Hz,0.2H,CH2-CH=N-O-),6.65(d,J=8.5Hz,0.8H,-C(=O)NH-CH-),6.59(d,J=8.5Hz,0.2H,-C(=O)NH-CH-),4.52(s,0.4H,-O-CH2-C(=O)-),4.47(s,1.6H,-O-CH2-C(=O)-),4.28-4.17(m,1H,-NH-CH(-CH2-)2),4.01-3.91(m,4H,four of (-CH(-CH2-)2)2),3.82(q,J=7.0Hz,6H,(CH3-CH2-O-)3Si-),3.78-3.70(m,4H,four of (-CH(-CH2-)2)2),3.70-3.63(m,2H,two of -NH-CH(-CH2-)2),3.57-3.49(m,2H,two of -NH-CH(-CH2-)2),3.47-3.39(m,2H,(-CH(-CH2-)2)2),2.43(m,0.4H,-CH2-CH2-CH-),2.24(q,J=6.0Hz,1.6H,-CH2-CH2-CH-),1.70-1.56(m,2H,-Si-CH2-CH2-CH2-),1.42(s,6H,six of ((-O-)2C(-CH3)2)2),1.40(s,6H,six of ((-O-)2C(-CH3)2)2),1.23(t,J=6.8Hz,9H,(CH3-CH2-O-)3Si-),0.77-0.69(m,2H,-Si-CH2-CH2-) 1313C NMR(CDCl3, 125 MHz): δ 169.5 (C×0.2, -CH2-C(=O)-NH-), 169.4 (C×0.8, -CH2-C(=O)-NH-), 154.0 (CH×0.2, -CH2-CH=N-O-), 153.0 (CH×0.8, -CH2-CH=N-O-), 98.1 (C×2, ((-O-)2C(-CH3)2)2), 72.7 (CH2×0.2, -O-CH2-C(=O)-), 72.4 (CH2×0.8, -O-CH2-C(=O)-), 70.7 (CH×2, (-O-CH(-CH2-)2)2), 66.4 (CH2×0.4, -NH-CH(-CH2-)2), 66.4 (CH2×1.6, -NH-CH(-CH2-)2), 62.4 (CH2×1.6, (-CH(-CH2-)2)2), 62.4 (CH2×0.4, (-CH(-CH2-)2)2), 62.3 (CH2×0.4, (-CH(-CH2-)2)2), 62.2 (CH2×1.6, (-CH(-CH2-)2)2), 58.4 (CH2×3, (CH3-CH2-O-)3Si-), 48.1 (CH×0.8, -NH-CH(-CH2-)2), 48.1 (CH×0.2, -NH-CH(-CH2-)2), 32.3 (CH2×0.8, -CH2-CH2-CH-), 28.8 (CH2×0.2, -CH2-CH2-CH-), 23.7 (CH3×1.6, (-C(-CH3)2)2), 23.7 (CH3×0.4, (-C(-CH3)2)2), 23.4 (CH3×0.4, (-C(-CH3)2)2), 23.4 (CH3×1.6, (-C(-CH3)2)2), 20.1 (CH2×0.8, -CH2-CH2-CH-), 19.8 (CH2×0.2, -CH2-CH2-CH-), 18.3 (CH3×3, (CH3-CH2-O-)3Si-), 10.4 (CH2×0.2, -Si-CH2-CH2-), 10.1 (CH2×0.8, -Si-CH2-CH2-) HRMS(ESI-TOF) m / z calcd for C 27 H 52 N2NaO 11 Si [M+Na] + 631.3238 found 631.3232

[0094] Example 6 (1) Synthesis of N-(1,3-bis((1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)propan-2-yl)-2-((1,3-dioxoisoindolin-2-yl)oxy)acetamide

[0095] [ka]

[0096] A solution of N-(carboxymethoxy)phthalimide (394.5 mg, 1.78 mmol) in acetonitrile was cooled to 0 °C and stirred for 30 min. HOBt (327.8 mg, 2.14 mmol) and EDC·HCl (410.3 mg, 2.14 mmol) were then added and stirred for 30 min. The reaction mixture was slowly allowed to return to room temperature, and compound 19 (1.24 g, 1.78 mmol) and triethylamine (750 μL, 5.35 mmol) were added and stirred at room temperature for 24 h. Ethyl acetate was added to the reaction mixture, and the organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 10 / 1) to obtain the target compound 20 (1.30 g, 1.4 mmol) as a yellow gummy liquid. FT-IR(KBr):3349,2990,2940,2865,1787,1731,1676,1534,1459,1373,1242,1192,1087,1031,932,870,827,753 and 703cm -1 . 1 H NMR (CDCl3,500MHz): δ7.90(dd,J=8.5,2.5Hz,2H),7.81(dd,J=8.5,2.5Hz,2H),4.73(s,2H)4.27(quint,1H), 3.97-3.94(m,7H),3.80-3.70(m,12H),3.67-3.53(m,11H),3.47(dquint,J=13.5,11Hz,4H),1.43,1.41,1.40 and 1.38(s,24H) or 1.40(dd,J=8.5,8Hz,24H) 13 C NMR(CDCl3,125MHz):δ166.48,163.33,134.94,123.94,98.17,78.62,77.22,76.80,71.06,68.69,62.54,49.31,24.50 and 22.73 HRMS(ESI-TOF): m / z calcd for C 43 H 66 N2NaO 18 [M+Na] + 921.4208 found 921.4226

[0097] (2) Synthesis of 1,3-bis((1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)propan-2-amine

[0098] [ka]

[0099] Compound 20 (150.0 mg, 0.17 mol) was dissolved in distilled methanol (10 mL). The temperature of the resulting solution was maintained at 35°C, and hydrazine monohydrate (13 μL, 12.6 mg, 0.25 mmol) was added and stirred for 24 hours. Chloroform was added to the reaction solution, which was then filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: ethyl acetate / methanol = 7 / 2) to obtain the target compound 21 (110 mg, 0.14 mmol, 85% yield) as a gel-like oil. FT-IR(KBr):3417,3318,2990,2865,1670,1515,1490,1440,1373,1248,1192,1075,926,814 and 722cm -1 . 1H NMR(CDCl3,500MHz):δ4.25(quint,1H),4.16(d,J=5.0Hz,2H),3.99-3.96(m,7H),3.79 -3.73(m,10H),3.68-3.52(m,13H),3.44(quint,4H)1.43(d,J=1.5Hz,12H),1.41(s,12 H). 13 C NMR(CDCl3,125MHz):δ169.2,98.2,78.7,74.8,71.2,71.1,68.8,68.6,68.5,62.5,62.4,48.7,23.9,23.7,23.5 and 23.3 HRMS(ESI-TOF): m / z calcd for C 35 H 64 N2NaO 16 [M+Na] + 791.4154 found 791.4178

[0100] (3) Synthesis of N-(1,3-bis((1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)propan-2-yl)-9,9-diethoxy-3,10-dioxa-4-aza-9-siladodec-4-enamide

[0101] [ka]

[0102] Compound 21 (100 mg, 0.13 mmol) was dissolved in ethanol (0.28 mL, 354 mg, 7.69 mmol), to which 90% triethoxysilylbutyraldehyde (39 μL, 40 mg, 0.16 mmol) was added and stirred at 50 °C for 2 h. The resulting mixture was concentrated and then subjected to silica gel column chromatography (eluent: ethyl acetate / acetone = 10 / 1) to obtain the target compound 22 (50 mg, 0.05 mmol, yield: 39%) as an oil. Analysis revealed that the ratio of isomers at the C=N double bond was 6:4, but the E / Z isomers could not be determined. FT-IR(neat):3428,2973,2926,2876,2245,1679,1520,1455,1372,1335,1284,1250,1227,1198,1086,940,830,792,757,732cm -1 1 H NMR(CDCl3,500MHz):δ7.51(t,J=6.0Hz,0.6H,-CH2-CH=N-O-),6.74(t,J=5.5Hz,0.4H,-CH2-CH=N-O-),6.69(d,J=8.5Hz,0.6H,-C(=O)NH-CH-),6.61(d,J=8.5Hz,0.4H,-C(=O)NH-CH-),4.51(s,0.8H,-O-CH2-C(=O)-),4.47(s,1.2H,-O-CH2-C(=O)-),4.27-4.14(m,1H,-NH-CH(-CH2-)2),4.03-3.90(m,8H,eight of ((-CH(-CH2-)2)2)2),3.89-3.78(m,7H,(CH3-CH2-O-)3Si-,one of (-CH(-CH2-)2)2),3.77-3.67(m, 9H,eight of ((-CH(-CH2-)2)2)2),one of (-CH(-CH2-)2)2),3.67-3.48(m,12H,-NH-CH(-CH2-)2,(-CH(-CH2-)2)2),3.47-3.38(m,4H,((-CH(-CH2-)2)2)2),2.45-2.38(m,0.8H,-CH2-CH2-CH-),2.23(q,J=7.0Hz,1.2H,-CH2-CH2-CH-),1.68-1.58(m,2H,-Si-CH2-CH2-CH2-),1.42(s,12H,twelve of (((-O-)2C(-CH3)2)2)2),1.40(s,12H,twelve of (((-O-)2C(-CH3)2)2)2),1.26-1.19(m,9H,(CH3-CH2-O-)3Si-),0.70-0.61 (m,2H,-Si-CH2-CH2-) 13C NMR(CDCl3,125MHz):δ169.4(C×0.4,-CH2-C(=O)-NH-),169.3(C×0.6,-CH2-C(=O)-NH-),153.8(CH×0.4,-CH2-CH=NO-),152.9(CH×0.6,-CH 2-CH=NO-),98.2(C×4,(((-O-)2C(-CH3)2)2)2),78.5(CH×0.8,(-CH(-CH2-)2)2),78.4(CH×1.2,(-CH(-CH2-)2)2),72.7(CH2×0.4,-O-CH2- C(=O)-),72.5(CH2×0.6,-O-CH2-C(=O)-),71.1(CH×2.4,((-O-CH(-CH2-)2)2)2),71.0(CH×1.6,((-O-CH(-CH2-)2)2)2),68.6(CH2×1.2,-N H-CH(-CH2-)2),68.6(CH2×0.8,-NH-CH(-CH2-)2),68.5(CH2×2.4((-CH(-CH2-)2)2),68.4(CH2×1.6,((-CH(-CH2-)2)2),62.5(CH2×4,four of ((-CH(-CH2-)2)2)2),62.4(CH2×4,four of ((-CH(-CH2-)2)2)2),58.4(CH2×1.2,(CH3-CH2-O-)3Si-),58.4(CH2×1.8,(CH3-CH2-O-)3Si-),48.7(CH×0.6,-NH-CH(-CH2-)2),48.6(CH×0.4,-NH-CH(-CH2-)2),32.4(CH2×0.6,-CH2-CH2-CH-),28.9(CH2×0.4,-CH2-CH2-CH-),24.2(CH3×4,((-O-)2 C(-CH3)2)2,23.0(CH3×1.6,((-O-)2C(-CH3)2)2,23.0(CH3×2.4,((-O-)2C(-CH3)2)2),20.2(CH2×0.6,-CH2-CH2-CH-),19.8 (CH2×0.4,-CH2-CH2-CH-),18.3(CH3×3,(CH3-CH2-O-)3Si-),10.5(CH2×0.4,-Si-CH2-CH2-),10.2(CH2×0.6,-Si-CH2-CH2-) HRMS(ESI-TOF): m / z calcd for C 45 H 84N2NaO 19 Si [M+Na] + 1007.5335 found 1007.5330

[0103] Example 7 (1) Synthesis of 5,5'-((2-isothiocyanatopropane-1,3-diyl)bis(oxy))bis(2,2-dimethyl-1,3-dioxane)

[0104] [ka]

[0105] A 0.05 M 1,4-dioxane solution (7.80 mL) of compound 14 (134.0 mg, 0.39 mmol) was stirred at room temperature while adding triphenylphosphine (122.1 mg, 0.47 mmol, 1.2 eq) and carbon disulfide (470 μL, 7.76 mmol). The reaction mixture was stirred in a sealed flask at 40° C. for 48 hours. The reaction mixture was then concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate / hexane = 1 / 1) to obtain the target compound 23 (125.0 mg, yield: 89%) as a white solid. FT-IR(neat) 2992,2968,2945,2906,2874,2114,1740,1471,1373,1309,1252,1199,1141,1087,1040,1001,968,940,887,856 and 824cm -1 1 H NMR(CDCl3,400MHz):δ3.99(dd,J=12.0,4.0Hz,4H),3.93(quint,J=4.8Hz,1H),3.77(dd,J=12.4,6. 0Hz,4H),3.70(dd,J=9.6,5.2Hz,2H),3.67(dd,J=10.0,5.6Hz,2H),3.48(quint,J=5.2Hz,2H),1.44 and 1.41(s,12H) 13C NMR(CDCl3,125MHz):δ136.5(NCS),98.3(C),71.4(CH),68.0(CH2),62.4(CH2),57.9(CH),23.8(CH3) and 23.4(CH3) HRMS(ESI-TOF) m / z calculation for C 16 H 27 NNaO6S [M+Na] + 384.1457 found 384.1433

[0106] (2) Synthesis of 1-(1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-yl)-3-(3-(triethoxysilyl)propyl)thiourea

[0107] [ka]

[0108] Compound 23 (100 mg, 0.28 mmol) was dissolved in ethanol (0.27 mL, 213 mg, 4.63 mmol), and 3-aminopropyltriethoxysilane (78 μL, 74 mg, 0.33 mmol) was added and stirred at room temperature for 2 h. The reaction solution was then concentrated, and the resulting residue was subjected to silica gel column chromatography (eluent: hexane / ethyl acetate = 3 / 1) to obtain the target compound 24 (144 mg, 0.25 mmol, yield: 89%) as a white oil. FT-IR(neat):3506,3327,3064,2974,2926,2880,1542,1449,1373,1337,1291,1251,1228,1199,1082,984,957,894,827,778,731cm -1 1H NMR(CDCl3,500MHz):δ6.57-6.12(br,2H,-NH-C(=S)-NH-),4.69-4.33(br,1H,-NH-CH(-CH2-)2),4.00(dd,J=3.5,12.5Hz,2H,two of (-CH(-CH2-)2)2),4.97(dd,J=3.5,12.5Hz,2H,two of (-CH(-CH2-)2)2),3.82(q,J=7.0Hz,6H,(CH3-CH2-O-)3Si-),3.81-3.71(m,6H,four of (-CH(-CH2-)2)2),two of -CH(-CH2-)2),3.61(dd,J=7.0,9.5Hz,2H,two of -CH(-CH2-)2),3.49-3.36(m,4H,-CH2-CH2-NH-,two of -CH(-CH2-)2),1.71(quint,2H,-CH2-CH2-CH2-),1.42(s,12H,((-O-)2C(-CH3)2)2),1.23(t,J=7.0Hz,9H,(CH3-CH2-O-)3Si-),0.69-0.61(m,2H,-Si-CH2-CH2-) 13 C NMR(CDCl3,125MHz):δ181.8(C,-NH-C(=S)-NH-),90.2(C×2,((-O-)2C(-CH3)2)2),70.7(CH×2,(-CH(-CH2-)2)2),62.6(CH2×2,-CH(-CH2-)2),61.9(CH2×4,(-CH(-CH2-)2)2),58.4(CH2×3,(CH3-CH2-O-)3Si-),53.7(CH,-NH-CH(-CH2-)2),47.0(CH2,-CH2-CH2-NH-),24.7(CH3×2,two of ((-O-)2C(-CH3)2)2),22.5(CH3×2,two of ((-O-)2C(-CH3)2)2),22.3(CH2,-CH2-CH2-CH2-),18.3(CH3×3,(CH3-CH2-O-)3Si-),7.8(CH2,-Si-CH2-CH2-) HRMS(ESI-TOF): m / z calcd for C 25 H 50 N2NaO9SiS [M+Na] +605.2904 found 605.2900

[0109] Example 8 (1) Synthesis of 5,5',5'',5'''-((((2-isothiocyanatopropane-1,3-diyl)bis(oxy))bis(propane-2,1,3-triyl))tetrakis(oxy))tetrakis(2,2-dimethyl-1,3-dioxane)

[0110] [ka]

[0111] To a solution of compound 25 (100.0 mg, 0.14 mmol) in tetrahydrofuran (30 μL), triethylamine (140 μL, 1.01 mmol) and carbon disulfide (43 μL, 0.72 mmol) were added at 0°C. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was then cooled to 0°C, and tosyl chloride (32 mg, 0.17 mmol) was added. The temperature of the reaction mixture was slowly raised to room temperature and stirred for an additional 2 hours. A 10% aqueous solution of potassium hydrogen sulfate (100 mL) was then slowly added, and the aqueous phase was extracted three times with dichloromethane (100 mL). The organic phase and the extract were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The resulting filtrate was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (eluent: dichloromethane / acetone=4 / 1) to obtain the target compound 26 (900 mg, 0.12 mmol, yield: 84%) as a colorless oil. FT-IR(KBr):2993,2940,2874,2071,1456,1373,1251,1228,1199,1044,938,829,755 and 668cm -1 1H NMR(CDCl3,500MHz):δ3.99-3.91(m,9H),3.80(dd,J=10.0,4.5Hz,2H),3.77-3.70( m,10H),3.66-3.57(m,6H),3.55(dd,J=10.0,5.5Hz,4H),3.45(dquint,J=5.25,1.5 Hz,4H),1.43 and 1.40(s,24H) 13 C NMR(CDCl3,125MHz):δ134.68(C,SCN),98.12(C×4),79.18(CH×1),77.39(CH×1),77.13(CH×1),76.88(CH×1),71.11(CH×2),69.96 (CH2×1,)68.92(CH2×4),62.43(CH2×8),62.39(CH2×1),58.14(CH×1),23.8(CH3×2),23.86(CH3×2),23.33(CH3×2),23.30(CH3×2) HRMS(ESI-TOF) m / z calculation for C 34 H 59 NNaO 14 S [M+Na] + 760.3554 found 760.3563

[0112] (2) Synthesis of 1-(1,3-bis((1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)propan-2-yl)-3-(3-(triethoxysilyl)propyl)thiourea

[0113] [ka]

[0114] Compound 26 (209 mg, 0.28 mmol) was dissolved in ethanol (0.3 mL, 237 mg, 5.14 mmol), to which 3-aminopropyltriethoxysilane (79 μL, 75 mg, 0.34 mmol) was added and stirred at room temperature for 1 hour. The resulting mixture was concentrated and then subjected to silica gel column chromatography (eluent: ethyl acetate / acetone = 8 / 1) to obtain the target compound 27 (206 mg, 0.21 mmol, yield: 76%) as a pale yellow oil. FT-IR(neat):3320,2973,2926,2877,1543,1455,1373,1340,1285,1250,1227,1198,1083,983,942,829,756,731,665cm -1 1 H NMR(CDCl3,500MHz):δ7.03-6.81(br,2H,-NH-C(=S)-NH-),4.87-4.65(br,1H,-NH-CH(-CH2-)2),4.60-3.92(m,8H,eight of ((-CH(-CH2-)2)2)2),3.87-3.69(m,10H,eight of ((-CH(-CH2-)2)2)2,two of -CH(-CH2-)2),3.81(q,J=7.0Hz,6H,(CH3-CH2-O-)3Si-),3.69-3.47(m,14H,two of -CH(-CH2-)2,(-CH(-CH2-)2)2,-CH2-CH2-NH-,(-CH(-CH2-)2)2),3.46-3.39(m,2H,two of ((-CH(-CH2-)2)2)2),3.38-3.31(m,2H,two of ((-CH(-CH2-)2)2)2),1.71-1.60(m,2H,-CH2-CH2-CH2-),1.42(s,6H,six of ((-O-)2C(-CH3)2)2)2),1.42(s,6H,six of ((-O-)2C(-CH3)2)2)2),1.40(s,12H,twelve of ((-O-)2C(-CH3)2)2)2),1.22(t,J=7.0Hz,9H,(CH3-CH2-O-)3Si-),0.66-0.60(m,2H,-Si-CH2-CH2-) 13C NMR(CDCl3,125MHz):δ182.4(C,-NH-C(=S)-NH-),98.3(C×1,one of ((-O-)2C(-CH3)2)2)2),98.1(C×3,three of ((-O-)2C(-CH3)2)2)2),79.2(CH×2,(-CH(-CH2-)2)2),71.0(CH×2,two of ((-CH(-CH2-)2)2)2),70.8(CH×2,two of ((-CH(-CH2-)2)2)2),69.4(CH2×1,one of ((-CH(-CH2-)2)2),68.6(CH2×3,three of ((-CH(-CH2-)2)2),62.8(CH2×2,-CH(-CH2-)2),62.5(CH2×3,three of ((-CH(-CH2-)2)2)2),62.4(CH2×3,three of ((-CH(-CH2-)2)2)2),62.0(CH2×2,two of ((-CH(-CH2-)2)2)2),58.3(CH2×3,(CH3-CH2-O-)3Si-),54.3(CH,-NH-CH(-CH2-)2),47.5(CH2,-CH2-CH2-NH-),23.8(CH3×4,four of ((-O-)2C(-CH3)2)2)2),23.3(CH3×4,four of (((-O-)2C(-CH3)2)2)2),22.6(CH2,-CH2-CH2-CH2-),18.3(CH3×3,(CH3-CH2-O-)3Si-),7.7(CH2,-Si-CH2-CH2-) HRMS(ESI-TOF): m / z calcd for C 43 H 82 N2NaO 17 SiS [M+Na] + 981.5001 found 981.5003

[0115] Example 9 (1) Synthesis of allyl (2-((1,3-bis((1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)propan-2-yl)amino)-2-oxoethoxy)carbamate

[0116] [ka]

[0117] A solution of 2-((((allyloxy)carbonyl)amino)oxy)acetic acid (125.9 mg, 0.72 mmol) in acetonitrile was cooled to 0 °C and stirred for 30 min. HOBt (143.17 mg, 0.93 mmol) and EDC·HCl (179.2 mg, 0.93 mmol) were added and stirred for 30 min. The reaction mixture was gradually allowed to warm to room temperature, and compound 25 (500 mg, 0.72 mmol) and triethylamine (300 μL, 2.16 mmol) were added. The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 7 / 1) to give the target compound 28 (400 mg, 0.47 mmol, yield: 65%) as a yellow gummy oil. FT-IR(KBr): 3510,3310,2991,2939,2874,1739,1672,1535,1455,1373,1334,1228,1199,1096,1043,939,829,755,732,666cm -1 1 H NMR(CDCl3,500MHz):δ5.97-5.89(m,1H),5.37-5.26(dd,2H),4.66(d,J=5.5Hz,2H),4.41(s,2H),4.25(q,1H),4 .0-3.96(m,8H),3.79-3.69(m,12H),3.66-3.54(m,10H),3.46-3.42(m,4H),1.43(d,J=5.0Hz,12H,1.42(s,12H) 13C NMR (CDCl3, 125MHz): δ168.46(C,C=0),157.67(C,C=O),131.80(CH×1),118.72(CH2×1),98. 28(C×4)78.72(CH×1),77.23(CH×1),75.39(CH2×1),71.19(CH×2),71.07(CH×2),68.85(CH2× 2), 68.72 (CH2 x 2), 68.60 (CH2 x 2), 66.54 (CH2 x 1), 62.53 (CH2 x 2), 62.49 (CH2 x 2), 62.44 (CH2 x 2), 62.39 (CH2 x 2), 49.18 (CH x 1), 23.82 (CH3 x 2), 23.62 (CH3 x 2), 23.56 (CH3 x 2), 23.40 (CH3 x 2) HRMS(ESI-TOF) m / z calculation for C 39 H 68 N2NaO 18 [M+Na] + 875.4365 found 875.4354

[0118] (2) Synthesis of allyl (2-((5,11-bis(((1,3-dihydroxypropan-2-yl)oxy)methyl)-1,15-dihydroxy-2,14-bis(hydroxymethyl)-3,6,10,13-tetraoxapentadecan-8-yl)amino)-2-oxoethoxy)carbamate

[0119] [ka]

[0120] Compound 28 (140 mg, 0.16 mmol) was dissolved in water (2 mL), and then ion exchange resin (Amberlyst-15, 0.140 g) was added and stirred at room temperature for 5 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to give compound 29 (80 mg, 0.12 mmol, 70% yield) as a yellow gummy oil. FT-IR(KBr): 3370,2933,2881,1731,1658,1549,1465,1413,1346,1262,1119,1052cm -1 1 H NMR(CD3OD,500MHz):δ6.02-5.93(m,1H),5.38-5.24(dd,2H),4.66(d,J=5.0Hz,2H) ,4.34(s,2H),4.24(q,1H),3.79-3.71(m,13H),3.68-3.58(m,17H),3.45(quint,4H) 13 C NMR(CD3OD,125MHz):δ169.76(C,C=O),158.49(C,C=O),132.19(CH×1),117.16(CH2×1),81.73(CH×2),81.70(CH×2),7 8.91(CH×2),75.03(CH2×1),69.42(CH2×4),68.50(CH2×2),65.99(CH2×1),61.12(CH2×4),61.08(CH2×4),49.54(CH×1) HRMS(ESI-TOF) m / z calculation for C 27 H 53 N2O 18 [M+H] + 693.3293 found 693.3285

[0121] Example 10: Synthesis of 2,2'-((2-isothiocyanatopropane-1,3-diyl)bis(oxy))bis(propane-1,3-diol) [ka]

[0122] Compound 23 (116.0 mg, 0.32 mmol) was added to a 0.1 N hydrogen chloride-methanol solution (3.0 mL) at room temperature and stirred for 3 hours. The reaction mixture was concentrated under reduced pressure to give target compound 30 (80 mg, 0.28 mmol, yield: 89%) as a colorless oil. FT-IR(KBr): 3393,2932,2882,2097,1641,1459,1344,1122,1051,970,848,672,496cm -1 1H NMR(CD3OD,400MHz):δ4.04(quint,J=5.4Hz,1H),3.84(dd,J=10.0,4.8Hz,2H),3.80(dd,J=10.0, 6.0Hz,2H),3.66(dd,J=11.6,4.8Hz,4H),3.60(dd,J=11.6,5.6Hz,4H),3.46(quint,J=5.6Hz,2H) 13 C NMR(CD3OD,125MHz):δ135.9(N=C=S),83.4(CH),70.5(CH2),62.6(CH),59.6(CH2) HRMS(ESI-TOF) m / z calculation for C 10 H 19 NO6SNa [M+Na] + 304.0831 found 304.0803

[0123] Example 11: Synthesis of 2,2'-((2-(3-((1,3-bis((1,3-dihydroxypropan-2-yl)oxy)propan-2-yl)oxy)-2-isothiocyanatopropoxy)propane-1,3-diyl)bis(oxy))bis(propane-1,3-diol)

[0124] [ka]

[0125] Compound 26 (1.60 g, 2.18 mmol) was dissolved in 0.1 N hydrogen chloride-methanol solution (10 mL) and stirred at room temperature for 3 hours. The solvent was removed under reduced pressure to give target compound 31 (1.2 g, 2.08 mmol, yield: 96%) as a gummy oil. FT-IR (KBr): 3372,2933,2876,2106,1653,1541,1458,1401,1345,1263,1204,1119,1071,831,677cm -1 1H NMR(CD3OD,400MHz):δ4.07(quint,J=4.8Hz,1H),3.89-3.55(m,30H),3.43(quint,J=4.4Hz,4H) 13 C NMR(CD3OD,125MHz):δ135.42(C,SCN),83.12(CH×2),83.10(CH×2),80.61(CH×2),71.01(CH2×3),70.77(CH2×3),62.53(CH2×4),62.52(CH2×4),59.51(CH×1) HRMS(ESI-TOF) m / z calculation for C 22 H 43 NNaO 14 S [M+Na] + 600.2302 found 600.2306

[0126] Example 12 (1) Synthesis of propan-2-one O-(1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxime

[0127] [ka]

[0128] A solution of compound 32 (474 ​​mg, 1.0 mmol) and acetoxime (292 mg, 4.0 mmol) in 1,4-dioxane was added to crushed potassium hydroxide (112 mg, 2.0 mmol) and stirred at 60 °C for 22 hours. The reaction mixture was then poured into water (20 mL). Extraction was performed with toluene (40 mL). The organic layer was washed three times with water and once with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give a pale yellow crude oil. The crude product was then purified by silica gel column chromatography (eluent: methylene chloride / ethyl acetate = 5 / 2 → 2 / 1) to give the target compound 33 (300 mg, 0.8 mmol, yield: 80%) as an oil. FT-IR(neat):2991,2940,2873,1654,1455,1372,1332,1282,1250,1227,1199,1154,1095,1043,937,831,732cm -1 1 H NMR(CDCl3,500MHz):δ4.24(quint,J=5.0Hz,1H,=NO-CH(-CH2-)2),3.95(dd,J=4.5,12.0Hz,4H,four of (-CH(-CH2-)2)2),3.72(dd,J=7.0,12.0Hz,4H,four of (-CH(-CH2-)2)2),3.69(d,J=5.5Hz,4H,=NO-CH(-CH2-)2),3.49(tt,J=4.5,7.0Hz,2H,(-O-CH(-CH2-)2)2),1.86(s,3H,three of (CH3-)2C=N-),1.85(s,3H,three of (CH3-)2C=N-),1.44(s,6H,six of ((-O-)2C(-CH3)2)2),1.40(s,6H,six of ((-O-)2C(-CH3)2)2) 13 C NMR(CDCl3,125MHz):δ155.4(C,(CH3-)2C=N-),98.1(C×2,((-O-)2C(-CH3)2)2),80.6(CH,-O-CH(-CH2-)2),70.9(CH×2,(-O-CH(-CH2-)2)2),67.8(CH2×2,-CH(-CH2-)2),62.7(CH2×4,(-CH(-CH2-)2)2),25.0(CH3×2,two of ((-O-)2C(-CH3)2)2),22.2(CH3×2,two of ((-O-)2C(-CH3)2)2),21.8(CH3,one of (CH3-)2C=N-),15.8(CH3,one of (CH3-)2C=N-) HRMS(ESI-TOF) m / z calcd for C 18 H 33 NNaO7[M+Na] + 398.2155 found 398.2163

[0129] (2) Synthesis of 2,2'-((2-(aminooxy)propane-1,3-diyl)bis(oxy))bis(propane-1,3-diol)

[0130] [ka] Compound 33 (375 mg, 1.0 mmol) was added with 1N hydrochloric acid (2 mL) and stirred at room temperature for 2 hours. The resulting reaction mixture was concentrated, followed by the addition of 1N hydrochloric acid (2 mL). The reaction vessel was placed in a water bath at 80 °C and concentrated under reduced pressure for 1.5 hours. This procedure was repeated four times. The resulting crude product was purified by column chromatography using a basic ion exchange resin ("Amberlite IRA910CT CL" manufactured by Organo Corporation) (eluent: ion-exchanged water only), followed by column chromatography using an acidic ion exchange resin ("Amberlite 200CT Na" manufactured by Organo Corporation) (eluent: ion-exchanged water only → 28% aqueous ammonia) to obtain a cloudy oil. The resulting oil was dissolved in methanol, the white cloudiness was removed using a syringe filter, and the resulting filtrate was concentrated to obtain the target compound 34 (220 mg, 0.86 mmol, yield: 86%) as an oil. FT-IR(KBr):3387,2946,2882,1646,1465,1412,1353,1220,1114,1055,996,975,911,831,677,571cm -1 1 H NMR(CD3OD,500MHz):δ3.89(quint,J=4.5Hz,1H),3.81-3.73(m,4H),3.67(dd,J=11.5 and 4.5Hz,4H),3.60(dd,J=12.0 and 6.0Hz,4H),3.45(quint,J=5.0Hz,2H) 13 C NMR(CD3OD,125MHz):δ82.55(CH),81.79(CH),68.78(CH2),61.14(CH2),61.05(CH2) HRMS(ESI-TOF) m / z calcd for C9H 21 NNaO7[M+Na] +278.1216 found 278.1238

[0131] Example 13: Synthesis of propan-2-one O-(1,3-bis((1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-yl)oxy)propan-2-yl)oxime

[0132] [ka]

[0133] A solution of compound 35 (348 mg, 0.41 mmol) and acetoxime (120 mg, 1.64 mmol) in 1,4-dioxane (0.82 mL) was added with crushed potassium hydroxide (46 mg, 0.82 mmol) and stirred at 60 °C for 24 h. The resulting reaction mixture was poured into water (20 mL). The mixture was extracted with dichloromethane (30 mL), and the extract was washed twice with water (10 mL) and once with saturated brine (10 mL). The extract was dried over anhydrous magnesium sulfate and concentrated to give a pale yellow oily crude product. The crude product was subjected to silica gel column chromatography (eluent: methylene chloride / acetone = 3 / 1) to give the target compound 36 (190 mg, 0.25 mmol, yield: 61%) as a pale yellow oily product. FT-IR(neat):2991,2939,2916,2873,2245,1654,1455,1372,1333,1283,1250,1227,1199,1153,1089,1043,997,938,920,831,732,647cm -1 1H NMR(CDCl3,500MHz):δ4.24(quint,J=5.0Hz,1H,=NO-CH(-CH2-)2),3.96(dd,J=4.0,4.0Hz,4H,four of (-CH(-CH2-)2)2),3.94(dd,J=4.0,4.0Hz,4H,four of (-CH(-CH2-)2)2),3.84-3.65(m,12H,(-CH(-CH2-)2)2,four of (-CH(-CH2-)2)2),3.63-3.50(m,10H,(-O-CH(-CH2-)2)2,four of (-CH(-CH2-)2)2,=NO-CH(-CH2-)2),3.50-3.42(m,4H,((-O-CH(-CH2-)2)2)2),1.86(s,3H,three of (CH3-)2C=N-),1.85(s,3H,three of (CH3-)2C=N-),1.43(s,12H,twelve of (((-O-)2C(-CH3)2)2)2),1.39(s,12H,twelve of (((-O-)2C(-CH3)2)2)2) 13 C NMR(CDCl3,125MHz):δ155.0(C,(CH3-)2C=N-),98.1(C×4,(((-O-)2C(-CH3)2)2)2),80.9(CH,-O-CH(-CH2-)2),78.8(CH×2,(-O-CH(-CH2-)2)2),70.9(CH×2,two of ((-O-CH(-CH2-)2)2)2),70.9(CH×2,two of ((-O-CH(-CH2-)2)2)2),69.3(CH2×2,-CH(-CH2-)2),68.5(CH2×2,two of (-CH(-CH2-)2)2),68.5(CH2×2,two of (-CH(-CH2-)2)2),62.6(CH2×4,four of ((-CH(-CH2-)2)2)2),62.6(CH2×4,four of ((-CH(-CH2-)2)2)2),24.6(CH3×4,four of (((-O-)2C(-CH3)2)2)2),22.2(CH3×4,four of (((-O-)2C(-CH3)2)2)2),21.8(CH3,one of (CH3-)2C=N-),15.8(CH3,one of (CH3-)2C=N-) HRMS(ESI-TOF): m / z calcd for C 36 H 65 NNaO 15 [M+Na] + 774.4252 found 774.4254

[0134] Example 14: Synthesis of 2,2',2'',2'''-((((2-(aminooxy)propane-1,3-diyl)bis(oxy))bis(propane-2,1,3-triyl))tetrakis(oxy))tetrakis(propane-1,3-diol)

[0135] [ka]

[0136] Compound 36 (190 mg, 0.25 mmol) was added with 1N hydrochloric acid (1 mL) and stirred at room temperature for 2 hours. The reaction mixture was concentrated, followed by the addition of 1N hydrochloric acid (1 mL), and the mixture was concentrated under reduced pressure at 50°C for 1.5 hours. This procedure was repeated four times. The resulting crude product was subjected to column chromatography (eluent: ion-exchanged water only) using a basic ion-exchange resin (Amberlite IRA910CT CL, Organo Corporation). It was then subjected to column chromatography (eluent: ion-exchanged water → 28% aqueous ammonia) using an acidic ion-exchange resin (Amberlite 200CT Na, Organo Corporation) to obtain a white, cloudy oil. The resulting oil was dissolved in methanol, and the cloudy white color was removed using a syringe filter. The resulting filtrate was concentrated to obtain the target compound 37 (90 mg, 0.16 mmol, yield: 64%) as an oil. FT-IR (neat):3370,2930,2879,1596,1461,1410,1348,1306,1245,1120,1068,973,908,845cm -1 1H NMR(CD3OD,500MHz):δ3.88-3.82(m,1H,H2NO-CH(-CH2-)2),3.82-3.67(m,14H,H2NO- CH(-CH2-)2),-CH(-CH2-)2)2),(-CH(-CH2-)2)2),3.64(dd,J=5.5,11.5Hz,8H,eight of ((-CH(-CH2-)2)2)2),3.57(dd,J=5.5,11.5Hz,8H,eight of ((-CH(-CH2-)2)2)2),3.43(quint,J=5.0Hz,4H,((-CH(-CH2-)2)2)2) 13 C NMR(CD3OD,125MHz):δ82.3(CH,H2NO-CH(-CH2-)2),81.7(CH×4,((-CH(-CH2-)2)2)2),79.0(CH×2,( -CH(-CH2-)2)2),69.3(CH2×4,(-CH(-CH2-)2)2),68.8(CH2×2,H2NO-CH(-CH2-)2),61.1(CH2×4,four of ((-CH(-CH2-)2)2)2),61.0(CH2×4,four of ((-CH(-CH2-)2)2)2) HRMS(ESI-TOF): m / z calcd for C 21 H 45 NNaO 15 [M+Na] + 574.2687 found 574.2672

[0137] Example 15: Anti-fogging test Compound 6 (599 mg) produced in Example 2(2) was dissolved in a mixed solvent (10 mL) of ethanol:water=50:50 to obtain a coating agent. Ordinary soft glass (thickness: 5 mm) without surface treatment or coating was cut into 10.5 cm x 4.5 cm pieces, washed three times with 1N hydrochloric acid and once with distilled water, and then wiped dry with a clean cloth. The coating agent (0.1 mL) was applied to a circular area of ​​approximately 2 cm in diameter in the center of the glass sample, and the sample was left to stand at room temperature for 30 minutes. The sample was then heated from the back side at approximately 100°C for 30 minutes using a heatable organic synthesis stirrer (Thermo Mighty Stirrer HHE-19G-U, manufactured by Koike Precision Machinery Co., Ltd.). The coated area was visually inspected, but no boundary between the coated and uncoated areas could be recognized. Furthermore, when the coated area was checked with a finger, no change in thickness was felt, and the area was evenly flat. To evaluate the anti-fogging properties, the glass sample was held coated side down over a steaming pot. The results are shown in Figure 1.

[0138] As shown in Figure 1, the area of ​​the glass sample that came into contact with the steam became cloudy and blocked visibility, but the circular area to which the coating agent of the present invention was applied remained clear, allowing the pattern on the paper behind it to be clearly seen. These results demonstrate that the coating agent of the present invention has excellent anti-fogging properties.

Claims

1. A coating agent for imparting anti-fogging and anti-fouling properties to a substrate, comprising a branched glycerol derivative represented by the following formula (I) as an active ingredient: 【Chemistry 1】 [In the formula, R 1 ~R 3 each independently represents a hydrocarbon group having 1 to 6 carbon atoms, R 4 and R 5 are independently H, C 1-6 Alkoxy-methyl group, C 2-6 Alkenyl group, tri(C 1-6 (Ar) alkyl) silyl group, or (Ar) p -methyl group (wherein Ar is optionally substituted C 6-10 aryl group, and p is an integer of 1 or more and 3 or less; 4 and R 5 are combined to form C 1-6 may form an alkanediyl group, X represents an (n+1)-valent linker group; n represents an integer of 2 or more and 6 or less, When n is an integer of 2 or more, a plurality of R 4 and R 5 may be the same or different.]

2. 2. The coating agent according to claim 1, wherein the substrate is made of glass.

3. The coating agent according to claim 2, further comprising water.

4. The coating agent according to claim 2 or 3, further comprising an acid catalyst.

5. 4. The coating agent according to claim 3, wherein the concentration of the branched glycerol derivative represented by formula (I) is 0.01 mol / L or more and 1 mol / L or less.

6. The coating agent according to any one of claims 2 to 5, further comprising a surfactant.

7. 1. A method for coating a surface of a substrate to impart anti-fog and anti-fouling properties, comprising: A method comprising the step of treating the surface of a substrate with the coating agent according to any one of claims 1 to 6.

8. The method according to claim 7, wherein the surface of the substrate is treated by immersing the substrate in the liquid coating agent, or by applying or spraying the liquid coating agent onto the surface of the substrate.

9. 9. The method according to claim 7 or 8, wherein the substrate is made of glass.

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