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光学活性化合物多羟基庚酸乙酯的合成
引用本文:王进欣,何玲,尤启冬,李瀛.光学活性化合物多羟基庚酸乙酯的合成[J].化学学报,2007,65(1):32-36.
作者姓名:王进欣  何玲  尤启冬  李瀛
作者单位:中国药科大学药学院,南京,210009;兰州大学功能有机分子化学国家重点实验室,兰州,730000;中国药科大学药学院,南京,210009;兰州大学功能有机分子化学国家重点实验室,兰州,730000
摘    要:以不对称环氧化和双羟化反应为构筑手性碳的关键步骤, 首次合成了(+)-(2R,3S,4S,5S)-6-甲基-4,5-环氧-2,3-二羟基-庚酸乙酯(5)和(-)-(2R,3S,4R,5S)-6-甲基-2,3,4,5-四羟基-庚酸乙酯(11). 找到一条适宜于该类化合物合成的简便有效且立体选择性好的合成路线. 初步生物活性测试表明, 化合物5, 11对HL60细胞具有抑制活性.

关 键 词:(+)-(2R  3S  4S  5S)-6-甲基-4  5-环氧-2  3-二羟基-庚酸乙酯  (-)-(2R  4R  5S)-6-甲基-2  3  4  5-四羟基-庚酸乙酯  不对称双羟化反应  抗肿瘤活性
收稿时间:2006-3-8
修稿时间:2006-03-082006-09-01

The Synthesis of the Optically Active Ethyl Polyhydroxy Heptanoate
WANG, Jin-Xin,HE, Ling,YOU,Qi-Dong,LI, Ying.The Synthesis of the Optically Active Ethyl Polyhydroxy Heptanoate[J].Acta Chimica Sinica,2007,65(1):32-36.
Authors:WANG  Jin-Xin  HE  Ling  YOU  Qi-Dong  LI  Ying
Affiliation:a. School of Pharmacy, China Pharmaceutical University, Nanjing 210009; b. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000
Abstract:The first synthesis of ethyl ( )-(2R,3S,4S,5S)-4,5-epoxy-2,3-dihydroxy-6-methyl heptanoate (5) and ethyl (-)-(2R,3S,4R,5S)-2,3,4,5-tetrahydroxy-6-methyl heptanoate (11) was achieved and the key steps involved the construction of chiral carbon centers by the asymmetric epoxidation and dihydroxylation. This efficiently concise strategy has better stereochemistry and is adapted to the synthesis of polyhydroxyl fatty acid analogues. The primary tests of compounds 5 and 11 showed better inhibitory activities against HL60 cell line.
Keywords:ethyl ( )-(2R  3S  4S  5S)-4  5-epoxy-2  3-dihydroxy-6-methyl heptanoate  ethyl (-)-(2R  3S  4R  5S)-2  3  4  5-tetrahydroxy-6-methyl heptanoate  asymmetric dihydroxylation  antitumor activity
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