171925-21-6

Basic information

• Product Name: 1,2,7,8-Indolizinetetrol, octahydro-, tetraacetate (ester), 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-
• Synonyms: 1,2,7,8-Indolizinetetrol, octahydro-, tetraacetate (ester), 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-
• CAS NO: 171925-21-6
• Molecular Formula: C16H23 N O8
• Molecular Weight: 0
• Mol File: 171925-21-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2,7,8-Indolizinetetrol, octahydro-, tetraacetate (ester), 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,7,8-Indolizinetetrol, octahydro-, tetraacetate (ester), 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-(171925-21-6)
• EPA Substance Registry System: 1,2,7,8-Indolizinetetrol, octahydro-, tetraacetate (ester), 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-(171925-21-6)

Safety Data

• Hazardous Substances Data: 171925-21-6(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 79831-76-8 (1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine 
• 171925-18-1 1,6,7-tri-O-benzoylcastanospermine 
• 171925-20-5 1,2,7-tri-O-benzoyl-1(R),2(S),7(S),8(R),8a(R)-tetrahydroxyoctahydroindolizidine 
• 171925-19-2 1,2,7-tri-O-benzyl-1(R),2(S),7(S),8(R),8a(R)-tetrahydroxyoctahydroindolizidine 
• 401789-09-1 (1S,2S,7R,8R,8aS)-1,2,7,8-tetrahydroxyindolizidine 
• 114364-61-3 ethyl 2,3,6-trideoxy-3,6-imino-4,5-O-isopropylidene-D-arabino-hexanoate 
• 545427-24-5 4-(1,2-dihydroxy-3-methoxycarbonyl-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester 
• 545427-22-3 methyl (E)-N-(tert-butoxycarbonyl)-2,3,4,5,8-pentadeoxy-5,8-imino-6,7-O-isopropylidene-D-arabino-oct-3-enonate 
• 545427-20-1 ethyl N-(tert-butoxycarbonyl)-2,3,6-trideoxy-3,6-imino-4,5-O-isopropylidene-D-arabino-2-hexonate 
• 545427-21-2 N-(tert-butoxycarbonyl)-2,3,6-trideoxy-3,6-imino-4,5-O-isopropylidene-D-arabino-2-hexose 
• 545427-27-8 (1S,2R,7R,8R,8aR)-1,2,7,8-tetraacetoxyindolizin-5-one 
• 149913-61-1 (1S,2R,7S,8S,8aR)-1,2,7,8-tetraacetoxyindolizin-5-one 
• 401789-06-8 (1S,2S,7R,8R,8aS)-1,2-bis-tert-butoxy-7-hydroxy-8-methoxycarbonyl-indolizidine 

Relevant articles and documents

Synthesis of polyhydroxyindolizidines from 5,6-dihydro-2H-pyran-2-one

(1aR,5aR,5bS,6S,7S)-6,7-Di-tert-butoxy-5-oxo-pyrrolidino[1,2-b]isoxazolidino [4,5-c]tetrahydropyran (8) prepared by (1,3)-dipolar cycloaddition of the cyclic nitrone 6 derived from tartaric acid to 5,6-dihydro-2H-pyran-2-one (7) was transformed into indolizidine 11 via a sequence of reactions involving methanolysis of the lactone ring, intramolecular alkylation of the nitrogen atom promoted by a carbontetrabromide-triphenylphosphine mixture and hydrogenolysis of the N-O bond. Decarboxylation of 11 provided known 7-hydroxylentiginosine derivative 14, whereas oxidative decarboxylation gave indolizidine 15 structurally related to castanospermine.

The Chemistry of Castanospermine, Part IV1: Synthetic Modifications at C-8

New methods for the selective functionalisation of castanospermine has enabled the synthesis of analogues and derivatives selectively modified at C-8.