1048680-82-5

Upstream product

• 1048680-81-4 3-azido-3-deoxy-β-D-allofuranose 
• 108-24-7 acetic anhydride 
• 300572-82-1 3-azido-3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-allofuranose 
• 21870-78-0 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 

Relevant academic research and scientific papers

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.

Stereocontrolled facile synthesis and biological evaluation of (3 S) and (3 R)-3-Amino (and Azido)-3-deoxy pyranonucleosides

This article describes the synthesis of (3 S) and (3 R)-3-amino-3-deoxy pyranonucleosides and their precursors (3 S) and (3 R)-3-azido-3-deoxy pyranonucleosides. Azidation of 1,2:5,6-di-O-isopropylidene-3-O-toluenesulfonyl- α-D-allofuranose followed by hy

Unexpected formation of complex bridged tetrazoles via intramolecular 1,3-dipolar cycloaddition of 1,2-O-cyanoalkylidene derivatives of 3-azido-3-deoxy-d-allose

An unexpected and interesting intramolecular side reaction occurred during the attempted synthesis of glycosyl cyanides upon treatment of 1-O-acetyl-3-azido-3-deoxyallose derivatives with TMSCN and different Lewis acids. Exo-1,2-O-cyanoalkylidene derivatives formed by neighboring group participation and attack of cyanide underwent, after Lewis-acid mediated isomerization to the endo-isomer, intramolecular azide-cyanide cycloaddition leading to the formation of tetrazoles embedded in bridged tetracyclic ring systems. The efficiency of cycloaddition is dependent on the ring structure of the sugar (pyranose or furanose). Of the studied molecules, 3-azido-1,2-O-cyanoethylidene-3-deoxy-allopyranose provides the most suitable scaffold for intramolecular [2+3] cycloaddition under exceptionally mild conditions. Our results highlight the capability of carbohydrates to act as scaffolds for the precise positioning of functional groups productive for a specific chemical reaction.

DERIVATIVES OF MONOSACCHARIDES FOR DRUG DISCOVERY

New compounds and methods for the preparation of combinatorial libraries of potentially biologically active compounds are based on monosaccharides of formula (I) being a derivative of a furanose or pyranose form of a monosaccharide.