98362-11-9

Basic information

• Product Name: (6R,7R,8R,8aR)-6,7,8-trihydroxyindolizidine
• CAS NO: 98362-11-9
• Molecular Weight: 173.212
• Mol File: 98362-11-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (6R,7R,8R,8aR)-6,7,8-trihydroxyindolizidine(CAS DataBase Reference)
• NIST Chemistry Reference: (6R,7R,8R,8aR)-6,7,8-trihydroxyindolizidine(98362-11-9)
• EPA Substance Registry System: (6R,7R,8R,8aR)-6,7,8-trihydroxyindolizidine(98362-11-9)

Safety Data

• Hazardous Substances Data: 98362-11-9(Hazardous Substances Data)

Upstream product

• 1228764-33-7 (6R,7R,8R,8aS)-6,7,8-tris(benzyloxy)-3,5,6,7,8,8a-hexahydroindolizine 
• 198493-30-0 tert-butyl (2S)-2-(2-oxoethyl)pyrrolidine-1-carboxylate 
• 1379528-14-9 (S,Z)-tert-butyl 2-(2-(tert-butyldimethylsilyloxy)vinyl)pyrrolidine-1-carboxylate 
• 1379528-16-1 (6S,7S,8R,8aR)-5-oxooctahydroindolizine-6,7,8-triyl triacetate 
• 1379528-15-0 (6S,7S,8R,8aR)-6,7,8-trihydroxyhexahydroindolizin-5(1H)-one 
• 1379528-08-1 (3S,4S,E)-3,4-bis(tert-butyldimethylsilyloxy)-3,4,8,9-tetrahydro-1H-azonin-2(7H)-one 
• 1379528-10-5 (S,Z)-2-(tert-butyldimethylsilyloxy)-1-(2-(2-(tertbutyldimethylsilyloxy)vinyl)pyrrolidin-1-yl)ethanone 
• 130464-32-3 (6R,7R,8R,8aR)-6,7,8-triacetoxyindolizidine 
• 1379528-13-8 (6S,7S,8R,8aS)-5-oxooctahydroindolizine-6,7,8-triyl triacetate 
• 1379528-12-7 (6S,7S,8R,8aS)-6,7,8-trihydroxyhexahydroindolizin-5-(1H)-one 
• 1379528-07-0 (3S,4S,Z)-3,4-bis(tert-butyldimethylsilyloxy)-3,4,8,9-tetrahydro-1H-azonin-2(7H)-one 
• 1379528-09-2 (S,E)-2-(tert-butyldimethylsilyloxy)-1-(2-(2-(tertbutyldimethylsilyloxy)vinyl)pyrrolidin-1-yl)ethanone 
• 1379528-11-6 (S,E)-tert-butyl 2-(2-(tert-butyldimethylsilyloxy)vinyl)pyrrolidine-1-carboxylate 
• 594840-59-2 2-[1-(tert-butyl-dimethyl-silanyloxy)-3-ethoxycarbonyl-allyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one (β-lactam), involving a cascade sequence of reactions as a key step

A divergent, short, and novel total synthesis of 1,6,8a-tri-epi- castanospermine (7) and 1-deoxy-6,8a-di-epi-castanospermine (8) has been developed via a common precursor, 15, obtained from d-mannitol derived β-lactam. The key step involves a one pot cascade sequence of trimethyl sulfoxonium ylide based cyclization of epoxy sulfonamide 14via epoxide ring opening, one carbon homologation followed by intramolecular cyclization. This journal is the Partner Organisations 2014.

A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides

A facile, versatile and stereoselective synthesis of bicyclic polyhydroxylated alkaloids as castanospermine analogues is described. The synthetic route started from methyl pyranosides. The key steps involved a high-yielding expeditious one-pot tandem reaction from alkenes to N-substituted δ-lactams. The δ-lactams were stereoselectively vinylated to give the dienes, which were followed by the ring-closing metathesis to produce the cyclized products. The functional group transformations of the resulting bicyclic compounds furnished diverse polyhydroxylated alkaloids in good yields. The Royal Society of Chemistry 2010.

Synthesis of 1-deoxy-6-epicastanospermine and 1-deoxy-6,8a-diepicastanospermine.

Extension of the carbon spine of 2,3;4,5-di-O-isopropylidene-beta-D-fructopyranoside by oxidation at C-1 followed by a Wittig reaction using the phosphorane Ph3P = CHCO2Et gave an oct-4-ulose derivative, which was then transformed into the key intermediat