91652-76-5

Upstream product

• 114894-82-5 benzyl 6-O-tetra-butyldiphenylsilyl-α-D-mannopyranoside 
• 100-51-6 benzyl alcohol 
• 91652-71-0 benzyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside 
• 91652-72-1 benzyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-talopyranoside 
• 91652-73-2 Trifluoro-methanesulfonic acid (3aS,4S,6R,7S,7aR)-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 114912-50-4 (3aS,4S,6R,7aR)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one 
• 3458-28-4 D-Mannose 
• 15548-45-5 (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 
• 91652-74-3 benzyl 4-azido-6-O-tert-butyldiphenylsilyl-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside 

Downstream Products

• 91652-77-6 benzyl E-4-azido-4,6,7-trideoxy-6-ene-2,3-O-isopropylidene-α-D-manno-octadialdopyranoside 
• 114894-85-8 (E)-3-((3aS,4S,7aS)-4-Benzyloxy-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-propenal 
• 72741-87-8 swainsonine 
• 85624-09-5 (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol 
• 91652-64-1 (1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane 
• 114894-86-9 (3aS,4S,5aR,9aR,9bS)-4-Benzyloxy-2,2,9-trimethyl-octahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-b]pyridine 
• 114894-83-6 benzyl 4-benzyloxycarbonylamino-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside 
• 114894-87-0 ((3aS,4S,6S,7S,7aS)-4-Benzyloxy-6-formyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-carbamic acid benzyl ester 
• 114894-84-7 benzyl 4-benzyloxycarbonylamino-4,6,7-trideoxy-6-ene-2,3-O-isopropylidene-α-D-manno-octadialdopyranoside 
• 95066-29-8 benzyl 4-amino-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside 
• 155688-49-6 benzyl 4,6-diazido-4,6-dideoxy-2,3-O-isopropylidene-D-mannopyranoside 
• 155688-50-9 benzyl 4,6-diamino-4,6-dideoxy-2,3-O-isopropylidene-D-mannopyranoside 
• 95189-02-9 1,4-dideoxy-1,4-imino-D-mannitol 

Relevant academic research and scientific papers

SYNTHESIS OF THE α-MANNOSIDASE INHIBITORS SWAINSONINE AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL FROM MANNOSE

4-azido-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside is a key intermediate in the syntheses of the α-mannosidase inhibitors, swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol, and of the α-galactosidase inhibitor 1,4-dideoxy-1,4-imino-D-lyxitol, from mannose.

ENANTIOSPECIFIC SYNTHESIS OF SWAINSONINE, (1S, 2R, 8R, 8aR)-1,2,8-TRIHYDROXYOCTAHYDROINDOLIZINE, FROM D-MANNOSE

An enantiospecific synthesis of swainsonine from D-mannose is described; the heterocyclic rings of swainsonine are constructed by two intramolecular reductive aminations caused by the catalytic hydrogenation of an azidoaldehyde with 5 equivalents of hydrogen.