74372-92-2

Upstream product

• 74372-91-1 2,3,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride 
• 194807-96-0 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride 
• 158852-31-4 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 40246-26-2 3,4,6-tri-O-benzyl-α-D-glucopyranose 
• 20672-66-6 3,4,6-tri-O-benzyl-D-mannopyranose 
• 1011723-04-8 glucal epoxide 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 

Downstream Products

• 149625-91-2 2'-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride 
• 1169827-74-0 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-β-D-glucopyranosylfluoride 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 

Relevant academic research and scientific papers

Synthesis of Mannosidase-Stable Man3and Man4Glycans Containing S-linked Manα1→2Man Termini

Oligomannose glycans are of interest as HIV vaccine components, but they are subject to mannosidase degradation in vivo. Herein, we report the synthesis of oligosaccharides containing a thio linkage at the nonreducing end. A thio-linked dimannose donor participates in highly stereoselective glycosylations to afford trimannose and tetramannose fragments. Saturation transfer difference nuclear magnetic resonance (STD NMR) studies show that these glycans are recognized by HIV antibody 2G12, and we confirm that the reducing terminal S-linkage confers complete stability against x. manihotis mannosidase.

Allyl protecting group mediated intramolecular aglycon delivery (IAD) of glycosyl fluorides

Stereospecific 1,2-cis-glycosylation of 2-O-allyl protected glucosyl and mannosyl fluorides can be achieved via a sequence of allyl isomerization, N-iodosuccinimide mediated tethering, and intramolecular aglycon delivery (IAD). Fluoride is advantageous as

Stereospecific synthesis of 1,2-cis glycosides by allyl-mediated intramolecular aglycon delivery. 2.The use of glycosyl fluorides.

[reaction: see text] Stereospecific 1,2-cis glycosylation of 2-O-allyl-protected glucosyl and mannosyl fluorides via a sequence of allyl isomerization, N-iodosuccinimide-mediated tethering, and intramolecular aglycon delivery (IAD) is reported. The use of

First synthesis of a digitalis saponin. Demonstration of the scope and limitations of a convergent scheme for branched oligosaccharide synthesis by the logic of glycal assembly

The synthesis of complex glycosides, with branching at C2, is demonstrated. The key element involves the use of a 1,2-oxirane donor. Upon glycosylation, a C2 hydroxyl is exposed to serve as the acceptor in the next glycosylation. Bra

CHEMICAL SYNTHESIS OF A (12)-D-GLUCOPYRANAN

1,2-Anhydro-3,4,6-tri-O-benzyl-α-D-glucopyranose was polymerized with a number of Lewis acids.Phosphorus pentafluoride at -60 deg C caused polymerization to a product rich in β linkages.Other Lewis acids at higher temperatures gave perbenzylated polysaccharides of lower molecular weight with less stereoselectivity.Debenzylation of the most-regular derivative gave a polysaccharide whose specific rotation was +14.7 degree and whose (13)C-n.m.r. spectrum had six absorptions corresponding to those of natural (12)-β-D-glucopyranans and additional minor peaks presumably due to some α-anomeric configurations.It was estimated to have ca. 90percent of β linkages.