73445-29-1Relevant academic research and scientific papers
A Streamlined Regenerative Glycosylation Reaction: Direct, Acid-Free Activation of Thioglycosides
Escopy, Samira,Singh, Yashapal,Stine, Keith J.,Demchenko, Alexei V.
, p. 354 - 361 (2020/12/02)
Our group has previously reported that 3,3-difluoroxindole (HOFox) is able to mediate glycosylations via intermediacy of OFox imidates. Thioglycoside precursors were first converted into the corresponding glycosyl bromides that were then converted into the OFox imidates in the presence of Ag2O followed by the activation with catalytic Lewis acid in a regenerative fashion. Reported herein is a direct conversion of thioglycosides via the regenerative approach that bypasses the intermediacy of bromides and eliminates the need for heavy-metal-based promoters. The direct regenerative activation of thioglycosides is achieved under neutral reaction conditions using only 1 equiv. NIS and catalytic HOFox without the acidic additives.
THE USE OF 2-O-ACYL-1-O-SULFONYL-D-GALACTOPYRANOSE DERIVATIVES IN β-D-GALACTOPYRANOSIDE SYNTHESIS
Vernay, Fredrick h.,Rachaman, Eliezer S.,Eby, Ronald,Schuerch, Conrad
, p. 267 - 274 (2007/10/02)
Several 1-O-sulfonyl derivatives of D-galactopyranose having a participating benzoyl or p-methoxybenzoyl group at O-2 were synthesized from the corresponding D-galactopyranosyl chloride derivatives by use of silver p-toluenesulfonate or trifluoroethanesulfonate in acetonitrile.The reaction of the 1-O-sulfonyl-D-galactopyranose derivatives with several alcohols in various solvents at different times and temperatures served as reactions to determine the best conditions for synthesizing stereoselectively β-D-galactopyranosides in high yields.This method was used to prepare, in good yield, several β-D-galactopyranosyl-containing disaccharides.
