277756-84-0

Basic information

• Product Name: phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside
• Synonyms: phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside
• CAS NO: 277756-84-0
• Molecular Weight: 385.444
• Mol File: 277756-84-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside(277756-84-0)
• EPA Substance Registry System: phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside(277756-84-0)

Safety Data

• Hazardous Substances Data: 277756-84-0(Hazardous Substances Data)

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 166516-67-2 phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside 
• 1394857-30-7 phenyl 4,6-O-benzylidene-1-thio-β-D-glucosaminopyranoside 
• 183875-02-7 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside 
• 202462-37-1 phenyl 2-azido-2-deoxy-1-thio-α/β-D-glucopyranoside 
• 183875-22-1 phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside 
• 183875-35-6 phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-azido-1-thiol-α-D-glucopyranoside 
• 171032-74-9 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose 
• 56644-75-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose 
• 169557-87-3 phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 371123-22-7 phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 
• 108-98-5 thiophenol 

Downstream Products

• 915154-77-7 C₄₆H₅₁N₃O₁₄ 
• 1394857-47-6 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate 
• 1394857-34-1 phenyl 2-azido-2-deoxy-3,6-di-O-benzyl-4-O-trichloroacetyl-1-thio-β-D-glucopyranoside 
• 1394857-41-0 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-trichloroacetyl-1-O-trichloroacetimidate-α/β-D-glucopyranoside 
• 1394857-42-1 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-trichloroacetyl-1-O-trichloroacetimidate-β-D-glucopyranoside 
• 1394857-60-3 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-trichloroacetyl-1-O-trichloroacetimidate-α-D-glucopyranoside 
• 1394857-50-1 methyl (phenyl 4-O-(2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside)-uronate 
• 1394857-51-2 methyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1→4)-(phenyl 3-O-benzyl-2-O-benzoyl-1-thio-β-L-idopyranoside)uronate 
• 1394857-52-3 methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside]uronate 
• 1394857-53-4 methyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl-(1→4)-(phenyl-2-O-benzoyl-3-O-benzyl-1-thio-β-L-idopyranoside)uronate 
• 1394857-57-8 methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-ido-pyranoside]uronate 

Relevant articles and documents

Synthesis of Rare Deoxy Amino Sugar Building Blocks Enabled the Total Synthesis of a Polysaccharide Repeating Unit Analogue from the LPS of Psychrobacter cryohalolentis K5T

Lipopolysaccharides (LPSs) play key roles in humoral immunity. Recently, the LPS structure of the Psychrobacter cryohalolentis K5T strain was reported. Due to the presence of unnatural amino sugars and branched linkages, its structure is unique. Herein we report the total synthesis of an LPS analogue of P. cryohalolentis K5T. After overcoming the issues like ring conformation changes and elimination of triflate, we were able to develop a strategy for the synthesis of the newly reported 2,3,4-triacetamido-2,3,4-trideoxy-l-arabinose derivative. Coupling of different donors with suitable acceptors from the nonreducing end to the reducing end and further functional group modifications delivered the protected LPS hexasaccharide repeating unit. After functional group modifications, we were unable to oxidize the hindered primary hydroxyl group to synthesize the target molecule. Alternatively, removal of the permanent protecting groups afforded the LPS hexasaccharide repeating unit analogue of Psychrobacter cryohalolentis K5T.

Synthesis and scalable conversion of L-iduronamides to heparin-related Di- and tetrasaccharides

A diastereomerically pure cyanohydrin, preparable on kilogram scale, is efficiently converted in one step into a novel L-iduronamide. A new regioselective acylation of this iduronamide and a new mild amide hydrolysis method mediated by amyl nitrite enable