Synthesis 2022; 54(03): 754-762
DOI: 10.1055/a-1654-2211
paper

Trimethylsilyl Esters as Novel Dual-Purpose Protecting Reagents

Jyun-Siao Chen
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Po-Hsun Huang
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Ya-Chi Hsieh
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Jen-Wei Liu
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Hsiao-Lin Hsu
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Kai-Min Zhang
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Ren-Tsung Wu
b   Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Miaoli 350, Taiwan
,
Ting-Shuo Chang
c   National Chutung Senior High School, Hsinchu 310, Taiwan
,
Yu-Hao Liu
c   National Chutung Senior High School, Hsinchu 310, Taiwan
,
Hsin-Ru Wu
c   National Chutung Senior High School, Hsinchu 310, Taiwan
,
Shun-Yuan Luo
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
› Author Affiliations
The authors thank the Ministry of Science and Technology in Taiwan (MOST 106-2113-M-005-007 and 107-2113-M-005-021 for S.-Y. Luo), National Chung Hsing University, and Chia Nan University of Pharmacy and Science for financial support.


Abstract

Trimethylsilyl esters, AcOTMS, BzOTMS, TCAOTMS, etc., are inexpensive and chemically stable reagents that pose a negligible environmental hazard. Such compounds prove to serve as efficient dual-purpose reagents to respectively achieve acylation and trimethylsilylation of alcohols under acidic or basic conditions. Herein, a detailed study on protection of various substrates and new methodological investigations is described.

Supporting Information



Publication History

Received: 09 August 2021

Accepted after revision: 27 September 2021

Accepted Manuscript online:
27 September 2021

Article published online:
17 November 2021

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