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532673

Sigma-Aldrich

(1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine

98%

Synonym(s):

(1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyoctahydroindolizidine, (1S,6S,7R,8R,8aR)-Octahydro-1,6,7,8-indolizinetetrol, 1,6,7,8-Tetrahydroxyoctahydroindolizine, Castanospermine

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About This Item

Empirical Formula (Hill Notation):
C8H15NO4
CAS Number:
79831-76-8
Molecular Weight:
189.21
Beilstein:
3588654
MDL number:
MFCD00017555
UNSPSC Code:
12352204
PubChem Substance ID:
24877905
NACRES:
NA.22

Quality Level

200

Assay

98%

optical activity

[α]20/D +80°, c = 0.9 in H2O

mp

213-217 °C (lit.)

SMILES string

[H][C@]12[C@@H](O)CCN1C[C@H](O)[C@@H](O)[C@@H]2O

InChI

1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1

InChI key

JDVVGAQPNNXQDW-TVNFTVLESA-N

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ1175
MKCK9872
MKCJ4924
MKBX4256V
MKBS8917V

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K S Ajish Kumar et al.
Organic & biomolecular chemistry, 6(4), 703-711 (2008-02-12)
The utility of a D-glucose-derived aziridine carboxylate was demonstrated for the synthesis of polyhydroxylated quinolizidine and indolizidine alkaloids. The chemoselective reduction of 1 followed by two-carbon homologation by the Wittig reaction afforded gamma,delta-aziridino-alpha,beta-unsaturated ester 9, which on regioselective nucleophilic aziridine
Julien Ceccon et al.
Organic letters, 8(21), 4739-4742 (2006-10-06)
[reaction: see text] An asymmetric total synthesis of (-)-swainsonine and (+)-6-epicastanospermine is described from a common intermediate, which is obtained through diastereoselective [2 + 2] cycloaddition of dichloroketene to a chiral enol ether.
Satoru Watanabe et al.
Antiviral research, 96(1), 32-35 (2012-08-08)
Celgosivir (6-O-butanoyl castanospermine), a pro-drug of the naturally occurring castanospermine, is an inhibitor of α-glucosidase I and II that is found to be a potent inhibitor of several enveloped viruses including all four serotypes of dengue virus. We showed previously
Vinod P Vyavahare et al.
Journal of medicinal chemistry, 50(22), 5519-5523 (2007-10-09)
Two new C-1 epimeric hydroxymethyl castanospermine congeners 2a and 2b, synthesized by stereocontrolled intramolecular double reductive amination of D-glucose derived beta-keto ester as a key step, showed impressive immuno-potentiating property. The bioactivity was mediated through up-regulation of T(H1)/T(H2) cytokine ratio.
Gang Liu et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(19), 5755-5768 (2010-04-10)
The asymmetric total synthesis of natural azasugars (+)-castanospermine, (+)-7-deoxy-6-epi-castanospermine, and synthetic (+)-1-epi-castanospermine has been accomplished in nine to ten steps from a common chiral building block (S)-8. The method features a powerful chiral relay strategy consisting of a highly diastereoselective
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