Glycosylation reaction catalyst, glycosylation method and application

A glycosidation reaction and catalyst technology, which is applied in the field of sugar chemistry, can solve the problems of lack of universal synthetic methods with wide applicability, and achieve the effects of accelerated reaction rate, high practical value, and excellent reactivity

Active Publication Date: 2022-01-14
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Stereoselectivity is affected by many factors such as chimera-assisted effects of protecting groups, solvents, counter ions, temperature, etc., and there is still a lack of general synthetic methods with broad applicability

Method used

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  • Glycosylation reaction catalyst, glycosylation method and application
  • Glycosylation reaction catalyst, glycosylation method and application
  • Glycosylation reaction catalyst, glycosylation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] 1. 1A-1H, 2A, 3C, 4C, 4E, 5C, and 5F are prepared according to the following operating procedures in this embodiment 1:

[0067]

[0068] The glycosylation reaction of the acceptor as a monohydroxy compound was carried out using the standard operating procedure (1): under an inert gas environment, the acceptor (1.2 equivalents) was added to the dissolved glycosyl donor (1.0 equivalents) and dry MS (100 mg / ml) in anhydrous DCM (0.01 M) was stirred in the greenhouse. The reaction mixture was then cooled to -65°C, and platinum(IV) chloride (0,1 equiv) was added thereto. Upon completion by TLC plate, the reaction was quenched by adding Et3N, diluted with DCM, and the precipitate was filtered off through a pad of Celite. The organic layer was washed with NaHCO3 (aq.) and NaCl (aq.), dried over Na2SO4, filtered and the solvent was removed under reduced pressure distillation. The resulting residue was purified by silica gel column chromatography to obtain the correspondi...

Embodiment 2

[0075] Embodiment 2: In this embodiment 2, 1I-1K, 1L-1P are prepared according to the following operating procedure:

[0076]

[0077] The acceptor is the glycosylation reaction of 1,2-cis-diol and 1,3-diol compound, and the standard operating procedure (2) is used: under an inert gas environment, the acceptor (1.2 equivalents) is added to the dissolved Glycosyl donor (1.0 equiv) and dry MS (100 mg / ml) in anhydrous DCM (0.01 M) was stirred in the greenhouse. The reaction mixture was then cooled to -78°C, and platinum(IV) chloride (0,1 equiv) was added thereto. It was detected by TLC plate until the reaction was completed, and finally Et was added 3 The reaction was quenched with N, diluted with DCM, and the precipitate was filtered through a pad of celite. NaHCO for organic layer 3 (aq.) and NaCl (aq.), washed with NaCl 2 SO 4 Dry, filter and remove the solvent under reduced pressure distillation. The resulting residue was purified by silica gel column chromatograph...

Embodiment 3

[0083] Embodiment 3: In this embodiment 3, 1Q-1Z is prepared according to the following operating procedures:

[0084]

[0085] The acceptor is the glycosylation reaction of 1,2-trans-diol and 1,2,3-triol, which is carried out by using the reaction standard operating procedure (3): under an inert gas environment, dissolve the acceptor (1.2 equivalents) into with dry MS (100 mg / ml) in anhydrous DCM (0.01 M) with stirring in the greenhouse. The reaction mixture was then cooled to -78°C, platinum(IV) chloride (0,1 eq) was added thereto and stirred for 10 min, and finally the glycosyl donor (1,0 eq) dissolved in anhydrous DCM was slowly added to the reaction middle. Upon completion by TLC plate, the reaction was quenched by adding Et3N, diluted with DCM, and the precipitate was filtered off through a pad of Celite. NaHCO for organic layer 3 (aq.) and NaCl (aq.), washed with NaCl 2 SO 4 Dry, filter and remove the solvent under reduced pressure distillation. The resulting...

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Abstract

The invention belongs to the technical field of sugar chemistry, and relates to a glycosylation reaction catalyst, a glycosylation method and application. The glycosylation method takes platinum chloride (IV) as a catalyst and is simple to operate, wide in substrate application range and high in reaction regioselectivity and stereoselectivity, and application of the method in glycosylation reaction is disclosed. According to the method, alpha-configuration O-glycosyl trichloroacetimidate is used as a donor, platinum (IV) chloride is used as a catalyst of an acid-base catalysis way, and a product mainly having a beta-configuration is obtained. In the method, a catalyst and a glycosyl acceptor are firstly combined to form a catalyst-acceptor adduct, so that proton acidity and oxygen affinity are increased, donor activation is enhanced, and acceptor transfer is carried out. According to the invention, the ligand binding capacity of platinum (IV) chloride and the characteristic that a diol receptor can be used as a bidentate ligand thereof are fully utilized, so that the method is not only suitable for construction of high-stereoselectivity glycosidic bonds of monohydroxyl receptors, but also can realize glycosidic bond construction with high regioselectivity and stereoselectivity of receptors of 1,3-diol, 1,2-cis-diol, 1,2-trans-diol, and 1,2,3-triol structures.

Description

technical field [0001] The invention belongs to the technical field of sugar chemistry, and relates to a glycosidation reaction catalyst, a glycosidation method and an application. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] As one of the three basic living substances, carbohydrates play an irreplaceable important role in life activities. In view of the important biological activity research value and pharmaceutical application value of sugar substances, it is of great significance to synthesize sugar substances with uniform and clear structure. [0004] The glycosidation reaction is the most critical reaction in the synthesis of carbohydrate compounds, and the most ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J27/13C07H1/00C07H1/06C07H15/18C07J71/00
CPCB01J27/13C07H1/00C07H1/06C07H15/18C07J71/0005Y02P20/55
Inventor 李天路彭鹏庄昊儒李彤杨跃
Owner SHANDONG UNIV
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