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Merck
CN

532673

(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

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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

Related Categories

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
MKCX5779
MKCQ1175
MKCK9872
MKCJ4924
MKBX4256V

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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
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
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
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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