64694-23-1

Upstream product

• 162118-38-9 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 
• 67576-77-6 1-O-methyl 2,3,4-tri-O-benzyl-L-fucopyranoside 
• 33639-75-7 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranose 

Downstream Products

• 143416-56-2 1-O-(4-pentenyl) 2,3,4-tri-O-benzyl-α-L-fucopyranoside 
• 1323140-37-9 methyl 3-O-benzyl-2-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 
• 1323140-39-1 methyl 3-O-benzyl-6-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 
• 1352718-49-0 methyl 2,3-di-O-methyl-6-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 
• 1352718-48-9 methyl 2,3-di-O-methyl-4-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 
• 1379442-50-8 methyl 3-O-benzyl-6-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-β-D-glucopyranoside 
• 1379442-52-0 methyl 3-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-glucopyranoside 
• 1379442-45-1 methyl 2-O-benzyl-4-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 
• 1379442-48-4 methyl 2-O-benzyl-6-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions

A general method has been developed for the formation of glycosyl chlorides and bromides from picolinic esters under mild and neutral conditions. Benchtop stable picolinic esters are activated by a copper(II) halide species to afford the corresponding products in high yields with a traceless leaving group. Rare β glycosyl chlorides are accessible via this route through neighboring group participation. Additionally, glycosyl chlorides with labile protecting groups previously not easily accessible can be prepared.

Solvent-free synthesis of glycosyl chlorides based on the triphenyl phosphine/hexachloroacetone system

Glycosyl chlorides, useful as glycosyl donors in glycoside synthesis and precursors in organic synthesis, can be easily prepared under solvent-free conditions by exposing a sugar hemiacetal to an equimolar mixture of PPh3 and hexachloroacetone

Defining oxyanion reactivities in base-promoted glycosylations

Saccharide oxyanions obtained by base treatment could be employed in glycosylation to give oligosaccharides with high stereo- and regioselectivities.

New method for regioselective glycosylation employing saccharide oxyanions

As an alternative concept for glycosylation, the prior activation of acceptor hydroxy groups for selective glycosidic bond formation, was investigated to give complex oligosaccharides. Oxyanions obtained from partially protected saccharides were glycosylated by employing glycopyranosyl halides, and the regiochemical results were studied. Initially, partially methylated methyl-α-D-glucopyranosides were used as a model system to study the underlying mechanistic principles of base-promoted glycosylation. High regioselectivities and stereospecific glycosidic bond formations were achieved, and the scope of the methodology was extended with different perbenzylated glycosyl donors.

Design and Synthesis of Peptide Mimetics of GDP-Fucose: Targeting Inhibitors of Fucosyltransferases

Novel peptide mimetics of GDP-fucose were designed and synthesized targeting inhibitors of the fucosyltransferases that transfer L-fucose from GDP-fucose to oligosaccharides, on the basis of the background that nikkomycin Z, a peptide mimetic of UDP-N-acetylglucosamine, shows potent inhibitory activity toward an N-acetylglucosamine transfer enzyme. The synthetic routes of the GDP-fucose mimetics take advantage of an enzymatic aldol reaction catalyzed by L-threonine aldolase to prepare the guanine carrying β-hydroxy-α- L-amino acid, a key synthetic intermediate.

A convenient preparation of glycosyl chlorides from aryl/alkyl thioglycosides

(equation presented) Because of the vast structural diversity encountered in the field of glycobiology, versatile methods for orthogonal oligosaccharide assembly are always of interest. Reported herein is the preparation of glycosyl chloride donors obtained by reaction of the corresponding thioglycoside precursors with chlorosulfonium chloride reagent 4. The crude chlorides thus obtained can be used directly in subsequent glycosylation reactions, and examples of the generality of this approach are provided.

Synthesis of glycosyl chlorides with acid-labile protecting groups

Glycosyl chlorides with acid-labile protecting groups were prepared from their corresponding alcohols under basic conditions in good yields. The synthesis of a 1,6-C-linked disaccharide was carried out via reaction of a glycosyl chloride with an aldehyde