Solid-phase synthesis of enantio-controlled lactic acid oligomers

被引：1

作者：

Kim, Seong-Ho ^{[1
,3
]}

Sim, Yong-Kyun ^{[1
]}

Kim, Bum-Tae ^{[1
]}

Kim, Yong Hwan ^{[2
]}

Kim, Yeong-Joon ^{[3
]}

Park, Seongsoon ^{[4
]}

Lee, Hyuk ^{[1
]}

机构：

[1] Korea Res Inst Chem Technol, Med Chem Res Ctr, Taejon 305600, South Korea

[2] Kwangwoon Univ, Dept Chem Engn, Seoul 139701, South Korea

[3] Chungnam Natl Univ, Dept Chem, Taejon 305764, South Korea

[4] Sungshin Womens Univ, Dept Chem, Ctr NanoBio Appl Technol, Inst Basic Sci, Seoul 136742, South Korea

来源：

TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 14-15期

关键词：

POLYMERS; POLYMERIZATION; DEPSIPEPTIDES; COPOLYMERS; DEPSIDES; DELIVERY; SYSTEMS; ESTERS;

D O I：

10.1016/j.tetasy.2011.08.021

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A synthetic method for lactic acid oligomers via solid-phase synthesis under mild reaction conditions with up to 99% yield is presented. The fine control of the chirality on each lactic acid unit of the oligomers was easily achieved by the substitution of (R)-THP-protected lactic acid (R)-2 by (S)-2 without alternating the procedure. The overall synthesis of the trimer and tetramer was completed in one and two days, respectively. Intramolecular cyclizations of enantio-controlled lactic acids were also attempted through the Yamaguchi macrolactonization or the Mitsunobu reaction. However, we were unable to isolate single cyclic oligomers but always obtained a mixture of cyclic oligomers. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1499 / 1504

页数：6

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