155417-78-0

Basic information

• Product Name: 3-Azido-3-deoxy-D-galactopyranose 1,2,4,6-tetraacetate
• Synonyms: 3-Azido-3-deoxy-D-galactopyranose 1,2,4,6-tetraacetate
• CAS NO: 155417-78-0
• Molecular Formula: C14H19N3O9
• Molecular Weight: 373.32
• Mol File: 155417-78-0.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: 3-Azido-3-deoxy-D-galactopyranose 1,2,4,6-tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Azido-3-deoxy-D-galactopyranose 1,2,4,6-tetraacetate(155417-78-0)
• EPA Substance Registry System: 3-Azido-3-deoxy-D-galactopyranose 1,2,4,6-tetraacetate(155417-78-0)

Safety Data

• Hazardous Substances Data: 155417-78-0(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 1083060-59-6 methyl 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-α-D-mannopyranoside 
• 1048680-81-4 3-azido-3-deoxy-β-D-allofuranose 
• 300572-82-1 3-azido-3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-allofuranose 
• 104875-44-7 3-azido-3-deoxy-D-glucopyranose 
• 13964-23-3 3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose 
• 27581-57-3 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 566164-19-0 1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose 
• 620630-83-3 1,2:5,6-di-O-cyclohexylidene-α-D-allofuranose 
• 21870-78-0 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 14133-35-8 methyl 3-amino-3-deoxy-α-D-mannopyranoside hydrochloride 
• 64952-23-4 3-hydroxy-2-(1-methoxy-2-oxoethoxy)propanal 
• 37073-79-3 Methyl-3-nitro-3-desoxy-α-D-mannopyranosid 

Relevant articles and documents

Synthesis of a cyclic tetramer of 3-amino-3-deoxyallose with axially oriented amino groups

A linear tetramer of β-(1 → 6)-linked 3-azido-3-deoxy-D-allose containing glycosyl donor and glycosyl acceptor functions in the terminal monosaccharide units was prepared starting from 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose. Cyclization of the linear tetramer under glycosylation conditions afforded the corresponding cyclic tetrasaccharide in 77% yield; its deprotection and reduction of the azido groups resulted in the formation of the cyclic tetramer of 3-amino-3-deoxy-D-allose with axial amino groups, a potential scaffold for the synthesis of tetravalent functional clusters.

Efficient synthesis of a galectin inhibitor clinical candidate (TD139) using a Payne rearrangement/azidation reaction cascade

Selective galectin inhibitors are valuable research tools and could also be used as drug candidates. In that context, TD139, a thiodigalactoside galectin-3 inhibitor, is currently being evaluated clinically for the treatment of idiopathic pulmonary fibrosis. Herein, we describe a new strategy for the preparation of TD139. Starting from inexpensive levoglucosan, we used a rarely employed reaction cascade: Payne rearrangement/azidation process leading to 3-azido-galactopyranose. The latter intermediate was efficiently converted into TD139 in a few simple and practical steps.

Cluster glycosides and heteroglycoclusters presented in alternative arrangements

Multivalent carbohydrates, or glycoclusters, are useful tools to study glycan-lectin and glycan-enzyme recognition processes and have wide potential therapeutic applicability. Herein, we report the synthesis of novel glycoclusters presenting glucopyranose