Improved Synthesis of 1-O-Acyl-β-d-Glucopyranose Tetraacetates.

Yu Chen,Huan Lu,Hui Dai,Xianhua Pan,Wansheng Yu,Yanyu Chen

doi:10.3390/molecules22040662

Abstract

An improved synthesis of 1-O-acyl glucosyl esters that avoids the use of expensive Ag reagents as well as the hydrolysis of unstable glucosyl bromides is reported. Notably, β-configuration products were obtained exclusively in good yields.

Highlights

IntroductionNumerous glycosyl esters have been investigated because of their biologically activity
Numerous glycosyl esters have been investigated because of their biologically activity.Numerous glycosyl esters have and beentuliposide-B investigated because of their biologically activity
We describe the improvement of this synthesis and synthesis and preparation of a series of2 O

Summary

Introduction

Numerous glycosyl esters have been investigated because of their biologically activity. Other alternative methods have been reported (Scheme 2), involving compounds. Other alternative methods have been reported (Scheme 2), involving compounds such as orthoesters [7,8], trifluoroacetates [9,10], TMSET glycosides [11], glucosyl fluorides [12,13,14,15], such as orthoesters [7,8], trifluoroacetates [9,10], TMSET glycosides [11], glucosyl fluorides [12,13,14,15], trichloroacetimidates [16], etc. The activation of the carboxylic acid group using the Mitsunobu protocol [17], DCC [18,19,20] or EDCI [21] were explored.

Results and Discussion

The reaction of glucosyl bromide

General Methods

Scaled-Up Synthesis of Compound 3

Scaled-Up Synthesis of Compound 24

Conclusions