A new method for the protection of carboxylic acids with a triisopropylsiloxymethyl group

Hikaru Yoshimura; Kohei Eto; Keisuke Takahashi; Jun Ishihara; Susumi Hatakeyama

doi:10.1248/cpb.c12-00490

A new method for the protection of carboxylic acids with a triisopropylsiloxymethyl group

Chem Pharm Bull (Tokyo). 2012;60(10):1334-9. doi: 10.1248/cpb.c12-00490.

Authors

Hikaru Yoshimura¹, Kohei Eto, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama

Affiliation

¹ Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.

PMID: 23036974
DOI: 10.1248/cpb.c12-00490

Abstract

An effective method for the protection of carboxylic acids with a triisopropylsiloxymethyl (TIPSOCH(2)) group is described. The reactions of various carboxylic acids with C(12)H(25)SCH(2)OTIPS in the presence of CuBr(2), Et(3)N, and molecular sieves 4A afford the corresponding triisopropylsiloxymethyl esters in good yields.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry
Amino Acids / chemistry
Carboxylic Acids / chemistry*
Esters / chemistry
Organosilicon Compounds / chemistry*

Substances

Alcohols
Amino Acids
Carboxylic Acids
Esters
Organosilicon Compounds