121195-24-2

Upstream product

• 65371-16-6 3,5-di-O-acetyl-6-deoxy-1,2-O-isopropylidene-6-azido-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 26275-20-7 6-deoxy-1,2-O-isopropylidene-6-(4'-methylbenzene)sulfonyloxy-D-glucofuranose 
• 23313-05-5 6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose 

Downstream Products

• 528566-59-8 6-nitro-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 528566-63-4 (1S,4S,5S,6R,7R)-6,7-bis(benzyloxy)-5-nitro-2-oxabicyclo[2.2.1]heptan-3-one 
• 528566-62-3 3,5-di-O-benzyl-6-deoxy-6-nitro-D-glucono-1,4-lactone 
• 528566-66-7 methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-α-D-glucofuranoside 
• 528566-71-4 methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-β-D-glucofuranoside 
• 528566-64-5 [((1S,4S,5S,6R,7R)-6,7-Bis-benzyloxy-3-oxo-2-oxa-bicyclo[2.2.1]hept-5-ylcarbamoyl)-methyl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis of tetrazole fused azepanes and quantum chemical topology study on the mechanism of the intramolecular cycloaddition reaction

The synthesis of novel tetrazolo azepanes from azido nitriles by 1,3 intramolecular dipolar cycloaddition starting from monosaccharide derivatives is described. A quantum chemical topological study on the intramolecular cyclization process has been conducted rendering a pseudo-concerted mechanism. Conformational study was done for the final products which showed a preferential twist boat conformation, theoretically suitable for mannosidase inhibition. However, the tetrazoles showed no significant inhibition of glycosidases.

A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S,3R,4R,5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE

Deoxymannojirimycin may be prepared in moderate amounts in an overall yield of 35percent in ten steps from diacetone glucose; the key step is formation of the piperidine ring by intramolecular nucleophilic displacement of a triflate at C-2 of a methyl glucofuranoside by a nitrogen function at C-6, irrespective of the anomeric configuration of the sugar.A synthesis of (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid is reported.