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532673

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

Name: (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine
Brand: ALDRICH

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

UNSPSC Code:

12352204

NACRES:

NA.22

PubChem Substance ID:

24877905

MDL number:

MFCD00017555

Beilstein/REAXYS Number:

3588654

Assay:

98%

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Properties

Quality Level

200

assay

98%

optical activity

[α]20/D +80°, c = 0.9 in H₂O

mp

213-217 °C (lit.)

functional group

hydroxyl

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

Description

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Efficient synthesis of (+)-1,8,8a-tri-epi-swainsonine, (+)-1,2-di-epi-lentiginosine, (+)-9a-epi-homocastanospermine and (-)-9-deoxy-9a-epi-homocastanospermine from a D-glucose-derived aziridine carboxylate, and study of their glycosidase inhibitory activities.

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

Asymmetric [2 + 2] cycloaddition: total synthesis of (-)-swainsonine and (+)-6-epicastanospermine.

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.

Synthesis of 1-deoxy-1-hydroxymethyl- and 1-deoxy-1-epi-hydroxymethyl castanospermine as new potential immunomodulating agents.

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.

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Global Trade Item Number

SKU	GTIN
532673-100MG	04061832986357