277756-84-0

Upstream product

• 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 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 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 
• 166516-67-2 phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside 

Downstream Products

• 277756-86-2 phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 
• 535961-73-0 phenyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 
• 154920-28-2 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate 
• 277756-87-3 phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 277756-89-5 phenyl 2-azido-3,6-di-O-benzyl-4-O-(tert-butyldimethylsilyl)-2-deoxy-1-thio-β-D-glucopyranoside 
• 819798-49-7 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside 
• 1280531-30-7 C₂₂H₂₃N₃O₆S 
• 1280531-31-8 C₂₁H₂₁NO₅S 
• 1280531-32-9 C₂₁H₂₃NO₅S 
• 1280531-33-0 C₂₃H₂₅NO₆S 
• 1280531-34-1 C₂₅H₂₇NO₇S 
• 1280531-41-0 C₂₅H₂₇NO₇S 
• 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 

Relevant academic research and scientific papers

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.

Scalable Synthesis of Anomerically Pure Orthogonal-Protected GlcN3 and GalN3 from d -Glucosamine

An improved and scalable synthesis of orthogonally protected d-glucosamine and d-galactosamine building blocks from inexpensive d-glucosamine has been developed. The key reaction is an inversion/migration step providing access to a fully orthogonal protec

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

Agonistic and antagonistic properties of a Rhizobium sin-1 lipid A modified by an ether-linked lipid

LPS from Rhizobium sin-1 (R. sin-1) can antagonize the production of tumor necrosis factor alpha (TNF-α) by E. coli LPS in human monocytic cells. Therefore these compounds provide interesting leads for the development of therapeutics for the prevention or