275812-74-3

Upstream product

• 275812-72-1 1-deoxy-3,4:5,6-di-O-isopropylidene-2-O-methanesulfonyl-1-(N-p-toluenesulfonyl)amino-D-glucitol 

Downstream Products

• 275812-82-3 N-[(R)-2-tert-Butoxy-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-4-methyl-benzenesulfonamide 
• 275812-90-3 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-C-phenyl-2-(N-p-toluenesulfonyl)amino-D-mannitol 
• 275813-02-0 N-{(R)-1-[(4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide 
• 275812-99-2 Acetic acid (R)-2-[(4R,5R)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(toluene-4-sulfonylamino)-ethyl ester 
• 275812-96-9 N-{(R)-2-Azido-1-[(4R,5R)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-4-methyl-benzenesulfonamide 

Relevant academic research and scientific papers

Synthesis of 1-deoxymannojirimycin analogues using N-tosyl and N-nosyl activated aziridines derived from 1-amino-1-deoxyglucitol

3,4;5,6-Diisopropylidene protected 1-amino-1-deoxy-D-glucitol was transformed into N-tosyl and N-nosyl activated aziridine intermediates, which underwent ring opening by reaction with various nucleophiles. The 5,6-diols resulting from selective hydrolysis of the terminal acetal group were subjected to (2-N→6-OH) cyclisation using two different methods for activation of 6-OH. Final deprotection of the N-nosyl and 3,4-acetal group proceeded smoothly to afford 6-substituted analogues of 1-deoxymannojirimycin.

Use of the N-tosyl-activated aziridine 1,2-dideoxy-1,2-iminomannitol as a synthon for 1-deoxymannojirimycin analogues

1-Amino-1-deoxy-D-glucitol was converted into the selectively protected title compound 4, an N-tosyl-activated aziridine that readily underwent ring opening with various nucleophiles. Further deprotection of the 5,6-diol moiety followed by ring closure under Mitsunobu conditions afforded the corresponding 6-substituted analogues of 1-deoxymannojirimycin. (C) 2000 Elsevier Science Ltd.