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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

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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Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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.
Matilde Aguilar-Moncayo et al.
Organic & biomolecular chemistry, 7(13), 2738-2747 (2009-06-18)
Synthesis of a panel of iso(thio)urea-type ring-modified castanospermine analogues bearing a freely mutarotating pseudoanomeric hydroxyl group results in tight-binding beta-glucosidase inhibitors with unusual binding signatures; the presence of an N-octyl substituent imparts a remarkable anomeric selectivity, promoting strong binding of
Tomohisa Kato et al.
Analytical biochemistry, 405(1), 103-108 (2010-06-24)
Saccharide primers, such as dodecyl beta-lactoside (Lac-C12), are unique artificial precursors of glycolipid synthesis. In culture media supplemented with saccharide primers, they are taken up by the cells in the culture media and glycosylated by cellular glycosyltransferases in the Golgi
Elena M Sánchez-Fernández et al.
Chemical communications (Cambridge, England), 46(29), 5328-5330 (2010-06-17)
sp(2)-Iminosugar-type castanospermine analogues bearing an alpha-configured N-, S-, or C-linked pseudoanomeric group have been designed as selective inhibitors of the neutral alpha-glucosidases involved in N-glycoprotein processing; evaluation in breast cancer cell growth indicated a significant antiproliferative potential that was dependent
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