154815-12-0

Basic information

• Product Name: (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine
• Synonyms: (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine
• CAS NO: 154815-12-0
• Molecular Weight: 303.401
• Mol File: 154815-12-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine(154815-12-0)
• EPA Substance Registry System: (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine(154815-12-0)

Safety Data

• Hazardous Substances Data: 154815-12-0(Hazardous Substances Data)

Upstream product

• 476171-46-7 7-[(4-methoxyphenyl)methoxy]-(3R,4R)-epoxy-1-heptene 
• 476171-51-4 (2S)-((1'R)-phenylmethoxy-4'-hydroxybutyl)-2,5-dihydropyrrole 
• 476171-68-3 6-[(4-methoxyphenyl)methoxy]-(2R,3R)-epoxyhexan-1-al 
• 476171-52-5 (8R,8aS)-8-benzyloxy-3,5,6,7,8,8a-hexahydroindolizine 
• 77-76-9 2,2-dimethoxy-propane 
• 162470-36-2 (-)-8-benzyloxy-swainsonine 
• 154815-09-5 (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one 
• 154321-89-8 (4aS,5R)-5-(benzyloxy)-2,4a,5,6,7,8-hexahydropyrido<1,2-b><1,2>oxazin-8-one 
• 154815-10-8 (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-(isopropylidenedioxy)propyl>piperidin-6-one 
• 154815-08-4 (2R,3R)-3-(benzyloxy)-2-<(Z)-3-(tert-butyldiphenylsilyloxy)-1-propenyl>piperidin-6-one 
• 154814-99-0 (E)-(R)-3-(benzyloxy)-1-<(p-tolylsulfonyl)oxy>-4,6-heptadiene 
• 154815-11-9 (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-hydroxy-1,2-(isopropylidenedioxy)propyl>piperidine 
• 154815-05-1 (2S,3R)-3-(benzyloxy)-2-<(Z)-3-hydroxy-1-propenyl>piperidin-6-one 
• 154815-00-6 (E)-(R)-4-(benzyloxy)-5,7-octadienonitrile 

Downstream Products

• 85624-09-5 (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol 
• 72741-87-8 swainsonine 

Relevant articles and documents

General approach to glycosidase inhibitors. Enantioselective synthesis of deoxymannojirimycin and swainsonine

(Chemical Equation Presented) Deoxymannojirimycin (2) and swainsonine (4) have been synthesized from each enantiomer of the same bicyclic carbarnate precursor 7. The key intermediate was prepared by a simple and efficient three-step synthesis involving RCM of the diene 8, which in turn is easily accessible in any configuration from enantiomerically enriched 2,3-epoxy-4-penten-1-ol 9.

Allylated monosaccharides as precursors in triple reductive amination strategies: Synthesis of castanospermine and swainsonine

The feasibility of the triple-reductive amination reaction for the synthesis of complex indolizidine frameworks is illustrated by application to the potent glycosidase inhibitors castanospermine and swainsonine. The target compounds were obtained from known carbohydrate precursors in yields of 23 and 14%, over nine and 13 steps, respectively. The iodoetherification reaction of allylated monosaccharides was shown to be a practical reaction for the synthesis of the tricarbonyl precursors for the key triple reductive amination reactions.

Asymmetric formal total synthesis of (-)-swainsonine

A new concise noncarbohydrate-based enantioselective approach to (-)-swainsonine 1 is described, utilizing the kinetic resolution of α-furfuryl amide 4 and the Sharpless AD reaction of 9a as key steps.Kinetic resolution of α-furfuryl amide 4 using the mod