329365-86-8

Basic information

• Product Name: ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide
• Synonyms: ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide
• CAS NO: 329365-86-8
• Molecular Weight: 616.843
• Mol File: 329365-86-8.mol

Chemical Properties

• CAS DataBase Reference: ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide(329365-86-8)
• EPA Substance Registry System: ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide(329365-86-8)

Safety Data

• Hazardous Substances Data: 329365-86-8(Hazardous Substances Data)

Upstream product

• 2043-76-7 S-ethyl methanethiosulfonate 
• 72174-24-4 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol 
• 75-08-1 ethanethiol 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 677031-68-4 S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranoyl) phenylthiosulfonate 
• 329365-81-3 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl methanethiosulfonate 

Downstream Products

• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 77870-91-8 (S)-2-((benzyloxycarbonyl)amino)-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)propanoate 
• 77870-90-7 (S)-2-((benzyloxycarbonyl)amino)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propanoate 
• 72174-24-4 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol 
• 64694-21-9 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 64694-22-0 1,2:5,6-di-O-isopropylidene-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1-3)-α-D-glucofuranose 
• 64842-82-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-[1:2,3:4]-di-O-isopropylidene-α-D-galactopyranoside 
• 41671-29-8 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 

Relevant articles and documents

REAGENTS AND METHODS FOR THE FORMATION OF DISULFIDE BONDS AND THE GLYCOSYLATION OF PROTEINS

Methods and reagents for the formation of disulfide bonds, particularly in proteins, peptides and amino acids. The methods and reagents are particularly useful for the controlled glycosylation of proteins, peptides and amino acids. The methods utilise thiosulfonate or selenenylsulfide compounds as reagents or intermediates. Some proteins and peptides comprising selenenylsulfide groups also form part of the invention.

Glycosyl disulfides: Novel glycosylating reagents with flexible aglycon alteration

Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28 simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent-active reactivity tuning strategies.

Glycosyl phenylthiosulfonates (glyco-PTS): novel reagents for glycoprotein synthesis.

Controlled site-selective glycosylation can be achieved by combining site-directed cysteine mutagenesis with chemical modification of the introduced thiol; a new class of more efficient chemoselective reagents, glycosyl phenylthiosulfonates, allow rapid glycosylations of representative simple thiols, peptides and proteins.

Glycosyldisulfides: A new class of solution and solid phase glycosyl donors

Mixed glycosyl disulfides are not only glycomimetics but also glycosyl donors that may be readily constructed in either armed ether-protected or disarmed ester-protected and in soluble or solid-supported forms from corresponding glycosyl methanethiosulfonates and used in the glycosylation of a variety of representative acceptors.