355145-91-4

Basic information

• Product Name: (2R,3S,4R)-(+)-N-(vinylacetyl)-2-vinyl-3,4-dibenzyloxypyrrolidine
• Synonyms: (2R,3S,4R)-(+)-N-(vinylacetyl)-2-vinyl-3,4-dibenzyloxypyrrolidine
• CAS NO: 355145-91-4
• Molecular Weight: 377.483
• Mol File: 355145-91-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S,4R)-(+)-N-(vinylacetyl)-2-vinyl-3,4-dibenzyloxypyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4R)-(+)-N-(vinylacetyl)-2-vinyl-3,4-dibenzyloxypyrrolidine(355145-91-4)
• EPA Substance Registry System: (2R,3S,4R)-(+)-N-(vinylacetyl)-2-vinyl-3,4-dibenzyloxypyrrolidine(355145-91-4)

Safety Data

• Hazardous Substances Data: 355145-91-4(Hazardous Substances Data)

Upstream product

• 355145-89-0 (2R,3S,4R)-(+)-N-tert-butoxycarbonyl-2-vinyl-3,4-dibenzyloxypyrrolidine 
• 1470-91-3 but-3-enoyl chloride 

Downstream Products

• 355145-94-7 (1S,2R,8aR)-(+)-1,2-dibenzyloxy-1,2,3,5,6,8a-hexahydroindolizine 
• 355145-95-8 (1S,2R,7R,8S,8aR)-(-)-1,2-dibenzyloxy-7,8-dihydroxyindolizidine 
• 355145-93-6 (1S,2R,7R,8S,8aR)-(-)-1,2-dibenzyloxy-7,8-dihydroxy-5-oxoindolizidine 
• 355145-92-5 (1S,2R,8aR)-(+)-1,2-dibenzyloxy-1,2,3,5,6,8a-hexahydro-5-oxoindolizine 

Relevant articles and documents

Stereoisomeric sugar-derived indolizines as versatile building blocks: Synthesis of enantiopure Di- and tetrahydroxyindolizidines

The synthesis of the sugar-derived (1S,2R,8aR)-1,2-di-O-isopropylidene-1,2,3,5,6,8a-hexahydro-5oxoindolizine (8) and by analogy of the corresponding stereoisomers ent-8 and ent-7, an epimer at C2 of ent-8, has been accomplished in a straightforward manner. The carbon-carbon double bond and the carbonyl functionalities on the six-membered ring make these nitrogen-containing heterocycles useful building blocks for the efficient preparation of a variety of enantiopure polyhydroxylated indolizidines of interest for their glycosidase inhibitory activity. We report here the synthesis of 2,8a-diepilentiginosine 12 from 8 and the preparation of stereoisomeric 1,2,7,8tetrahydroxyindolizidines 9-11 performed by OsO4-catalyzed double bond syn dihydroxylation of 7 and 8, followed by deoxygenation of the amide group.