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532673

Sigma-Aldrich

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

98%

Sinônimo(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

Fórmula empírica (Notação de Hill):
C8H15NO4
Número CAS:
79831-76-8
Peso molecular:
189.21
Beilstein:
3588654
Número MDL:
MFCD00017555
Código UNSPSC:
12352204
ID de substância PubChem:
24877905
NACRES:
NA.22

Ensaio

98%

atividade óptica

[α]20/D +80°, c = 0.9 in H2O

pf

213-217 °C (lit.)

cadeia de caracteres SMILES

[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

chave InChI

JDVVGAQPNNXQDW-TVNFTVLESA-N

Categorias relacionadas

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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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.
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
Laurent Chabaud et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(9), 2744-2756 (2008-01-24)
The carboazidation of chiral allylsilanes has been investigated by varying the nature of the substituents at the silicon center and on the carbon framework. The influence of temperature and the nature of the sulfonyl azide, as well as the stereochemistry
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.
Thomas Jensen et al.
The Journal of organic chemistry, 74(22), 8886-8889 (2009-10-28)
A nine-step synthesis of (+)-castanospermine has been accomplished in 22% overall yield from methyl alpha-D-glucopyranoside. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 6-iodoglucopyranoside, ring-closing olefin metathesis, and strain-release transannular cyclization to afford the indolizidine skeleton of the
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