532673
栗精胺
98%
别名:
(1S,6S,7R,8R,8aR)-1,6,7,8-四羟基八氢吲哚里西定, (1S,6S,7R,8R,8aR)-八氢-1,6,7,8-吲嗪四醇, 1,6,7,8-四羟基八氢吲嗪, 栗树精胺
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关于此项目
经验公式（希尔记法）:
C8H15NO4
化学文摘社编号:
分子量:
189.21
UNSPSC Code:
12352204
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3588654
Assay:
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
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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.
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
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