130609-19-7

Upstream product

• 130539-17-2 4-O-benzoyl-2,3-di-O-benzyl-N,6-O-carbonyl-1,5-dideoxy-1,5-imino-D-galactitol 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 100-39-0 benzyl bromide 
• 130539-15-0 2,3-di-O-benzyl-N,6-O-carbonyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 130609-18-6 N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol 
• 130539-13-8 2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol 
• 130539-14-9 2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 130539-16-1 2,3-di-O-benzyl-N,6-O-carbonyl-1,5-dideoxy-1,5-imino-4-O-methanesulfonyl-D-glucitol 
• 203253-85-4 (2R,3R,4R,5S)-4,5-Bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-chloromethanesulfonyloxy-piperidine-1-carboxylic acid benzyl ester 
• 203253-86-5 (2R,3S,4R,5S)-3-Benzoyloxy-4,5-bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidine-1-carboxylic acid benzyl ester 
• 203253-84-3 (2R,3R,4R,5S)-4,5-Bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-methanesulfonyloxy-piperidine-1-carboxylic acid benzyl ester 
• 161045-53-0 N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol 
• 203253-87-6 4-O-benzoyl-2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-galactitol 

Downstream Products

• 130539-18-3 2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-D-galactitol 

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).