203253-83-2

Upstream product

• 3396-11-0 cesium acetate 
• 203253-82-1 Acetic acid (6S,7S,8R,8aR)-8-(tert-butyl-diphenyl-silanyloxy)-3-oxo-6-(toluene-4-sulfonyloxy)-hexahydro-oxazolo[3,4-a]pyridin-7-yl ester 
• 203253-80-9 (6S,7R,8R,8aR)-6,7-Bis-benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-hexahydro-oxazolo[3,4-a]pyridin-3-one 
• 203253-81-0 (6S,7R,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-6,7-dihydroxy-hexahydro-oxazolo[3,4-a]pyridin-3-one 
• 161045-53-0 N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol 

Downstream Products

• 14199-63-4 1-deoxymannojirimycin 

Relevant academic research and scientific papers

Chemical transformation of a 1-deoxynojirimycin derivative into 1-deoxymannojirimycin and 1-deoxygalactostatin

Treatment of 2,3-di-O-benzyl-N-benzyloxycarbonyl-6-O-t-butyldiphenylsilyl-1,5-dideoxy-1,5- imino-D-glucitol (4) with sodium hydride resulted in an intramolecular cyclization concomitant with silyl migration, giving the carbamate derivative 5 in good yield. This was efficiently converted into 1-deoxymannojirimycin (2) via regioselective p-toluenesulfonylation followed by an inversion reaction at the C-2 position. On the other hand, the monochloromethylsulfonate 10 obtained from 4 underwent configurational change at the C-4 position by the action of sodium benzoate. The resulting benzoate 11 was deprotected to afford 1-deoxygalactostatin (3).