Glucosamine donor and application thereof

Abstract

The invention discloses a glucosamine donor and application thereof. According to the glucosamine donor, N, N-dimethylformamide is introduced into a C-2 position nitrogen atom for performing N, N-diacetyl protection; an electron-rich activated (armed) protecting group is introduced to at least one position of glucosamine C-3, C-4 and C-6, wherein the N, N-diacetyl has an ortho-group participationeffect, can generate a single beta-selective glycosylation product, and can be removed from acyl groups at other positions by a one-kettle method under mild conditions such as methanol / sodium methoxide and the like so that the synthesis efficiency is improved. The iso-head leaving group of the glucosamine donor can be halogen, glucosinolate, imine ester, pentene alkoxy, hydroxyl and the like, andcan react with different receptors to construct a beta-glucosidic bond so that the reaction efficiency is high.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a class of glucosamine donor and its application in generating β-glucosidic bonds. Background technique [0002] As an important part of natural glycoconjugates, amino sugars are widely found in microorganisms, animals, plants, and humans in the form of polysaccharides, oligosaccharides, glycoproteins, glycolipids, and cell membrane structural components, and play important roles in molecular recognition, signal transduction, cell Differentiation, genetic development, transplant rejection, blood group differentiation, target recognition and other biological processes play an important role. Among the naturally occurring amino sugars, glucosamine is one of the most abundant monosaccharides. Most of these glycoconjugates are linked by β-glycosidic bonds and exist in the form of N-acetyl derivatives. Likewise, they also all have important biological functions. For exam...

AI Technical Summary

Problems solved by technology

However, acetyl-protected glucosamine tends to generate poorly active oxazophos intermediates in the glycosylation reaction, and other amino-protecting groups, such as LNT tetrasaccharides containing phthalimide groups, require high temperature removal of phthalimide The formimide group, which leads to the instability of the sialoglycosidic bond at high temperature, the dimethylmaleimide (dimethylmaleoyl) strategy and the trichloroacetyl strategy have similar problems, and need to reintroduce N- Acetyl group, which reduces the yield of a large amount of synthetic aminoglycosides

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