ASSIGNMENT OF RELATIVE AND ABSOLUTE-CONFIGURATION OF ACYCLIC POLYOLS AND AMINOPOLYOLS BY CIRCULAR-DICHROISM - TRENDS FOLLOW FISCHER SUGAR FAMILY TREE

被引:21
作者
ZHOU, P [1 ]
BEROVA, N [1 ]
WIESLER, WT [1 ]
NAKANISHI, K [1 ]
机构
[1] COLUMBIA UNIV,DEPT CHEM,NEW YORK,NY 10027
关键词
1,2-POLYOLS; 1-AMINOPOLYOLS; ABSOLUTE CONFIGURATION; CD; EXCITON CHIRALITY METHOD;
D O I
10.1016/0040-4020(93)80020-T
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reference CD curves (measured in methylcyclohexane) of a homologous series of 1,2-polyols up to pentols derivatized as anthroates at 1-OH and p-methoxycinnamates at the remaining hydroxyl groups show a systematic trend that greatly simplifies assignments of relative and absolute configurations. The same trend also holds for the corresponding 1-aminopolyols, but not for 2-aminopolyols.
引用
收藏
页码:9343 / 9352
页数:10
相关论文
共 17 条
[1]   BACTERIAL STEROL SURROGATES - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF BACTERIOHOPANETETROL SIDE-CHAIN BY HEMISYNTHESIS OF ITS DIASTEREOISOMERS [J].
BISSERET, P ;
ROHMER, M .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2958-2964
[2]  
HARADA N, 1987, 2ND P FECS INT C CIR, P209
[3]  
HARADA N, 1983, CIRCULAR DICHROIC SP, P156
[4]   TRITERPANES IN OPTICALLY ACTIVE PETROLEUM DISTILLATES [J].
HILLS, IR ;
WHITEHEA.EV .
NATURE, 1966, 209 (5027) :977-&
[5]   A CONVENIENT ROUTE TO AN ACETYLENIC-C35 HOPANOID AND THE ABSOLUTE-CONFIGURATION OF THE SIDE-CHAIN OF AMINOBACTERIOHOPANETRIOL [J].
NEUNLIST, S ;
ROHMER, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (12) :830-832
[6]   HOPANOIDS .1. GEOHAPANOIDS - THE MOST ABUNDANT NATURAL-PRODUCTS ON EARTH [J].
OURISSON, G ;
ALBRECHT, P .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (09) :398-402
[7]   HOPANOIDS - PALAEOCHEMISTRY AND BIOCHEMISTRY OF A GROUP OF NATURAL-PRODUCTS [J].
OURISSON, G ;
ALBRECHT, P ;
ROHMER, M .
PURE AND APPLIED CHEMISTRY, 1979, 51 (04) :709-729
[8]   BIGGER AND BETTER HOPANOIDS [J].
OURISSON, G .
NATURE, 1987, 326 (6109) :126-127
[9]   HOPANOIDS .2. BIOHOPANOIDS - A NOVEL CLASS OF BACTERIAL LIPIDS [J].
OURISSON, G ;
ROHMER, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (09) :403-408
[10]  
WIESLER WT, 1989, CROAT CHEM ACTA, V62, P211