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
Satoru Watanabe et al.
Antiviral research, 96(1), 32-35 (2012-08-08)
Celgosivir (6-O-butanoyl castanospermine), a pro-drug of the naturally occurring castanospermine, is an inhibitor of α-glucosidase I and II that is found to be a potent inhibitor of several enveloped viruses including all four serotypes of dengue virus. We showed previously
Vinod P Vyavahare et al.
Journal of medicinal chemistry, 50(22), 5519-5523 (2007-10-09)
Two new C-1 epimeric hydroxymethyl castanospermine congeners 2a and 2b, synthesized by stereocontrolled intramolecular double reductive amination of D-glucose derived beta-keto ester as a key step, showed impressive immuno-potentiating property. The bioactivity was mediated through up-regulation of T(H1)/T(H2) cytokine ratio.
Julien Ceccon et al.
Organic letters, 8(21), 4739-4742 (2006-10-06)
[reaction: see text] An asymmetric total synthesis of (-)-swainsonine and (+)-6-epicastanospermine is described from a common intermediate, which is obtained through diastereoselective [2 + 2] cycloaddition of dichloroketene to a chiral enol ether.
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
K S Ajish Kumar et al.
Organic & biomolecular chemistry, 6(4), 703-711 (2008-02-12)
The utility of a D-glucose-derived aziridine carboxylate was demonstrated for the synthesis of polyhydroxylated quinolizidine and indolizidine alkaloids. The chemoselective reduction of 1 followed by two-carbon homologation by the Wittig reaction afforded gamma,delta-aziridino-alpha,beta-unsaturated ester 9, which on regioselective nucleophilic aziridine
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