150271-24-2

Upstream product

• 50-00-0 formaldehyd 
• 150271-21-9 2-Amino-4,6-O-(R-benzylidene)-N-butyl-1,2,5-trideoxy-1,5-imino-D-glucitol 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 160711-08-0 2,3-Anhydro-4,6-O-(R-benzylidene)-1,5-dideoxy-1,5-imino-D-mannitol 
• 150271-17-3 2-Azido-4,6-O-(R-benzylidene)-1,2,5-trideoxy-1,5-imino-D-glucitol 
• 150271-18-4 2-Azido-4,6-O-(R-benzylidene)-N-butyl-1,2,5-trideoxy-1,5-imino-D-glucitol 
• 150338-26-4 2,3-Anhydro-4,6-O-(R-benzylidene)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol 
• 138381-83-6 4,6-O-(R-Benzylidene)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 138381-86-9 4,6-O-(R-Benzylidene)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2-O-(p-toluenesulfonyl)-D-glucitol 
• 150271-15-1 2-Azido-4,6-O-(R-benzylidene)-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-D-glucitol 

Relevant academic research and scientific papers

NUCLEOPHILIC OPENING OF N-CARBOALKOXY-2,3-ANHYDRO-1-DEOXYMANNOJIRIMYCIN. A USEFUL METHOD FOR THE SYNTHESES OF 2-, 3- AND 2,3-DISUBSTITUTED 1-DEOXYNOJIRIMYCIN ANALOGS

A useful methodology for the synthesis of a number of 2-, 3- and 2,3-disubstituted deoxynojirimycin analogs is reported.It has been found that the epoxides in stereoselectively synthesized N-carboalkoxy-2,3-anhydro-1-deoxymannojirimycins (4 and 5) react with N-, S- and F-nucleophiles to give a mixture of gluco and altro products.The 3-azido altro compound (12b) yields the desired gluco derivative (40) by oxidation, in situ epimerization at C-3, followed by stereoselective reduction of the carbonyl group.The azido intermediate (12a) affords the 2,3-diazido gluco compound (51) by double inversion at C-3.Attempts have been made to understand the factors contributing to the opening of epoxides (4, 5 and 9) by different nucleophiles.