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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
UNSPSC Code:
12352204
NACRES:
NA.22
PubChem Substance ID:
24877905
MDL number:
MFCD00017555
Beilstein/REAXYS Number:
3588654
Assay:
98%

Key Documents

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Product Name

(1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine, 98%

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

SMILES string

[H][C@]12[C@@H](O)CCN1C[C@H](O)[C@@H](O)[C@@H]2O

InChI key

JDVVGAQPNNXQDW-TVNFTVLESA-N

assay

98%

optical activity

[α]20/D +80°, c = 0.9 in H2O

mp

213-217 °C (lit.)

functional group

hydroxyl

Quality Level

200

Related Categories

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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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
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.
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
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