138875-24-8

Upstream product

• 1385089-78-0 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-idopyranoside 
• 1385089-80-4 methyl 2,3-di-O-benzyl-β-D-idopyranoside 
• 128184-62-3 (2R,3S,4R,5R)-3,4,5-Tris-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran 

Downstream Products

• 126661-83-4 cyclophellitol 
• 138794-98-6 Methanesulfonic acid (1S,2R,3R,4R,5R,6S)-3-(diethyl-isopropyl-silanyloxy)-2-(diethyl-isopropyl-silanyloxymethyl)-4,5,6-trihydroxy-cyclohexyl ester 
• 128184-67-8 (2S,3R,4S,5R,6R)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone 
• 128184-66-7 (1R,2R,3S,4S,5R)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene 
• 138794-97-5 (2S,3R,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanone 
• 128184-69-0 (1S,2R,3R,4R,5R,6S)-1,2,3-tribenzyloxy-6-methanesulfonyloxy-4-<(1-methylethyl)diethylsilyl>oxy-5-<<(1-methylethyl)diethylsilyl>oxy>methylcyclohexane 
• 128184-68-9 (1S,2R,3S,4R,5R,6S)-2,3,4-tribenzyloxy-5-<(1-methylethyl)diethylsilyl>oxy-6-<<(1-methylethyl)diethylsilyl>oxymethyl>cyclohexanol 
• 128184-68-9 (1R,2R,3S,4R,5R,6S)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanol 
• 139402-99-6 (1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate 
• 103597-18-8 methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-α-D-glycero-D-gluco-octopyranoside 
• 103597-22-4 methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-β-L-glycero-D-gluco-octopyranoside 
• 126836-22-4 (2R,4aR,6S,7R,8aR)-7-[(S)-Hydroxy-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methyl]-6-methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one 
• 128184-64-5 methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside 
• 128184-65-6 (2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal oxime 

Relevant academic research and scientific papers

Total syntheses of glucosidase inhibitors, cyclophellitols

A β-D-glucosidase inhibitor, cyclophellitol heptane-2,3,4-triol, 1> and its epoxide diastereomer, 1,6-epicyclophellitol (2) have been synthesized by using an intramolecular -cycloaddition of a n

Studies on the 6-homologation of β-D-idopyranosides

β-D-Idopyranosides are interesting sugars because of their unusual conformational flexibility in the pyranosyl ring, and also their β-1,2-cis-anomeric configuration. Here we report our studies of the regioselective opening of 4,6-O-benzylidene-protected β-D-idopyranosides under reducing conditions, and the subsequent 6-homologation via Swern oxidation and Wittig olefination to afford a 6,7-dideoxy-β-D-ido-hept-6-enopyranoside. This olefination product was found to adopt predominantly 1C4 conformation in solution by NMR experiments, which places the vinyl group at a more sterically hindered axial position and creates difficulty in subsequent hydroborations.

Enantiospecific total synthesis of a β-glucosidase inhibitor, cyclophellitol

Cyclophellitol has been synthesized from L-glucose through an intramolecular cycloaddition of a nitrile oxide derived from an oxime.