通过温和裂解亚甲基缩醛实现 1,2-和 1,3-二醇的新型区域控制保护。

Novel regiocontrolled protection of 1,2- and 1,3-diols via mild cleavage of methylene acetals.

机构信息

Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka Suita, Osaka 565-0871, Japan.

出版信息

Org Lett. 2009 Nov 19;11(22):5138-41. doi: 10.1021/ol902088b.

DOI:10.1021/ol902088b

PMID:19821584

Abstract

The regiocontrolled protection of unsymmetrical 1,2- and 1,3-diols has been developed. Different types of protected diols are available from the methylene acetal in a one-pot procedure. Highly regioselective protection of diols with a silyl group at the less hindered hydroxy group as well as with a MOM group at the more hindered one were achieved. The reaction conditions are mild without affecting other functional groups including acid-labile function.

摘要

已开发出非对称 1,2-和 1,3-二醇的区域控制保护方法。可通过亚甲基缩醛在一锅法中获得不同类型的保护二醇。可高区域选择性地保护位阻较小的羟基带有硅基基团、位阻较大的羟基带有甲氧基甲醚基团的二醇。反应条件温和，不会影响包括酸不稳定官能团在内的其他官能团。