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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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Diastereoselective nitrenium ion-mediated cyclofunctionalization: total synthesis of (+)-castanospermine.

Edward G Bowen et al.

Organic letters, 12(22), 5330-5333 (2010-10-23)

The asymmetric total synthesis of the α-glucosidase inhibitor (+)-castanospermine is reported. The central theme in our approach to this polyhydroxylated alkaloid is the simultaneous generation of the piperidine ring and the C-1/8a erythro stereodiad through the diastereoselective, oxamidation of an

Inhibition of the exo-beta-D-glucosaminidase CsxA by a glucosamine-configured castanospermine and an amino-australine analogue.

Benjamin Pluvinage et al.

Organic & biomolecular chemistry, 7(20), 4169-4172 (2009-10-02)

The synthesis of amino-derivatives of castanospermine and australine and their characterisation as inhibitors of the exo-beta-D-glucosaminidase CsxA through enzyme kinetics and X-ray structural analysis is described.

Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation.

Julien Ceccon et al.

Organic & biomolecular chemistry, 7(10), 2029-2031 (2009-05-08)

An asymmetric synthesis of (+)-castanospermine is presented in which enol ether metathesis-hydroboration/oxidation is used for stereoselective installation of the trans-trans hydroxyl groups on the piperidine ring of the alkaloid.

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Global Trade Item Number

SKU	GTIN
532673-100MG	04061832986357