(6S)-Methyl-L-swainsonine [(1R, 2S, 6S, 8S, 8aS)-6-methyloctahydroindolizine-1,2,8-triol]

被引：2

作者：

Hakansson, Anders E.

Horne, Graeme

Fleet, George W. J.

Watkin, David J.

机构：

[1] Univ Oxford, Chem Res Lab, Dept Organ Chem, Oxford OX1 3TA, England

[2] Univ Oxford, Chem Res Lab, Dept Chem Crystallog, Oxford OX1 3TA, England

来源：

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS | 2007年 / 63卷

关键词：

D O I：

10.1107/S1600536806052111

中图分类号：

O7 [晶体学];

学科分类号：

0702 ; 070205 ; 0703 ; 080501 ;

摘要：

(6S)-Methyl-L-swainsonine, C9H17NO3, together with the 6R-epimer, was formed in a synthetic sequence in which there was an ambiguity in configuration at position C-6. This ambiguity was resolved by establishing the relative stereochemistry of the title compound by X-ray crystallographic analysis. The absolute configuration was determined by the use of D-glycero-D-gulo-heptono-1,4-lactone as the starting material.

引用

页码：O210 / O212

页数：3

共 50 条

[1] FACILE SYNTHESES OF CYCLOPHELLITOL AND ITS (1R,6S)-DIASTEREOISOMERS, (1R,2S,6S)-DIASTEREOISOMERS, (2S)-DIASTEREOISOMERS FROM (-)-QUINIC ACID
SHING, TKM
TAI, VWF
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (12) : 995 - 997
[2] (-)-QUINIC ACID IN ORGANIC-SYNTHESIS .4. SYNTHESES OF CYCLOPHELLITOL AND ITS (1R,6S)-DIASTEREOISOMER, (2S)-DIASTEREOISOMER, (1R,2S,6S)-DIASTEREOISOMER
SHING, TKM
TAI, VWF
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (14): : 2017 - 2025
[3] Synthesis of protected (2S,6S,8S)-indolizin-9 one amino acid
Shimizu, M
Nemoto, H
Kakuda, H
Takahata, H
HETEROCYCLES, 2003, 59 (01) : 245 - 255
[4] (6S,7S,8R,8aS)-6-Ethylperhydroindolizine-7,8-diol
Svorc, Lubomir
Vrabel, Viktor
Zuziova, Jozefina
Marchalin, Stefan
Kozisek, Jozef
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1666 - U243
[5] SYNTHESIS OF OPTICALLY-ACTIVE METHYL (-)-(2R,3R,6S,8S)-NONACTATE
GOMBOS, J
HASLINGER, E
ZAK, H
SCHMIDT, U
MONATSHEFTE FUR CHEMIE, 1975, 106 (01): : 219 - 222
[6] (4R,6S,7S,8S,8aS)-6-Ethyl-7,8-dihydroxy-4-methyl-1,2,3,5,6,7,8,8a-octahydroindolizin-4-ium iodide
Vrabel, Viktor
Sivy, Julius
Svorc, Lubomir
Safar, Peter
Zuziova, Jozefina
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O3520 - U365
[7] SYNTHESIS OF (+)-(2S,6S)-TRANS-ALPHA-IRONE AND OF (-)-(2S,6S)-TRANS-GAMMA-IRONE
HELMLINGER, D
FRATER, G
HELVETICA CHIMICA ACTA, 1989, 72 (07) : 1515 - 1521
[8] (6S, 7S, 8S, 8aS)-6-Ethyl-3-oxo1,2,3,5,6,7,8,8a- octahydroindolizine7,8- diyl diacetate
Vrabel, Viktor
Svorc, Lubomir
Safar, Peter
Marchalin, Stefan
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68 : O662 - U1820
[9] (6S,7S,8S,8aS)-6-Ethyl-7,8-dihydroxy-1,5,6,7,8,8a-hexahydroindolizin-3(2H)-one monohydrate
Vrabel, Viktor
Svorc, Lubomir
Safar, Peter
Zuziova, Jozefina
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O3112 - U2631
[10] A facile synthesis of (6S,1′S)-(+)-hernandulcin and (6S,1′R)-(+)-epihernandulcin
Kim, JH
Lim, HJ
Cheon, SH
TETRAHEDRON, 2003, 59 (38) : 7501 - 7507

← 1 2 3 4 5 →