161664-79-5

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 93381-69-2 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl bromide 
• 604767-74-0 di-n-butyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl) phosphate 
• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 78687-40-8 methyl 2,3,4-tri-O-benzyl-6-O-(trimethylsilyl)-α-D-glucopyranoside 
• 124684-91-9 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-α-D-mannopyranosyl fluoride 

Downstream Products

• 136824-11-8 methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 138181-82-5 methyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Rational optimization of the mannoside building block for automated electrochemical assembly of the core trisaccharide of GPI anchor oligosaccharides

We have developed a carbohydrate building block of mannosides based on DFT calculations, electrochemical analysis, and automated solution-phase synthesis. The optimized building block in hand was used to prepare the core trisaccharide of GPI anchor oligos

METHODS FOR GLYCOSYLATION

Provided herein are methods of glycosylation in the formation of disaccharides, trisaccharides, and oligosaccharides using fluoroglycosides, silyl ether glycosides and a triaryl borane catalyst.

Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation

Challenges in the assembly of glycosidic bonds in oligosaccharides and glycoconjugates pose a bottleneck in enabling the remarkable promise of advances in the glycosciences. Here, we report a strategy that applies unique features of highly electrophilic b

AuIII-halide/phenylacetylene-catalysed glycosylations using 1-o-acetylfuranoses and pyranose 1,2-orthoesters as glycosyl donors

1-O-Acetylfuranoses and pyranose 1,2-orthoesters were activated with an AuIII halide/phenylacetylene relay catalyst system, and they acted as excellent glycosyl donors. Thus, 1-O-acetyl-D-ribofuranose, 1-O-acetyl-D-lyxofuranose, and 1,2-orthoesters selectively gave the corresponding 1,2-trans glycosides, whereas 1-O-acetyl-D-arabinofuranose and 1-O-acetyl-D-xylofuranose both gave mixtures of 1,2-trans and 1,2-cis glycosides, with the 1,2-trans glycosides predominating. A new glycosylation method has been developed for 1-O-acetylfuranoses and pyranose 1,2-orthoesters, using AuIII halides and phenylacetylene as relay catalyst systems. Good anomeric selectivity was observed for 1-O-acetylfuranoses, and excellent selectivity was observed for pyranose 1,2-orthoesters. The corresponding glycosides were formed in moderate to good yields.

Synthesis of glycosyl phosphates from 1,2-orthoesters and application to in situ glycosylation reactions

A series of glycosyl phosphates were prepared in high yield by treatment of the corresponding 1,2-orthoesters with dibutyl phosphate. Glycosyl phosphates are efficient glycosylating agents even when used in crude form or when generated in situ. The immuno

The synthesis of β-mannopyranosides by intramolecular aglycon delivery: scope and limitations of the exciting methodology

The synthesis of β-mannopyrosides by intramolecular aglycon delivery is shown to proceed with complete stereoselectivity in six separate cases.This strategy has been successfully applied to the synthesis of several disaccharides, including octyl 3,6-di-O-