Synthesis 2021; 53(11): 2000-2006
DOI: 10.1055/s-0040-1705990
paper

Development of a Novel Method for Trimethylsilylation of Saccharides­

Jyun-Siao Chen
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Yi-Fan Ke
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Heng-Yan Lin
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Wesley Lin
b   Morrison Academy, Taichung 406, Taiwan
,
Wei-Chung Yen
c   Taipei Municipal Neihu High School, Taipei 114, Taiwan
,
Hsin-Ru Wu
d   Instrumentation Center, MOST, National Tsing Hua University, Hsinchu 300, 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 (MOST) in Taiwan (MOST 107-2113-M-005-021) and National Chung Hsing University for financial support.


Abstract

The trimethylsilyl (TMS) group is widely used in carbo­hydrate synthesis, although this protecting group is unstable and its post-synthetic purification challenging. The successful trimethylsilyl­ation of carbohydrates mediated by recyclable and efficient acidic catalyst PTA/HMDS and the novel reagent, TMSOAc (TEA/TMSOAc), under alkaline condition is reported. The advantages of these methods are that the reactions proceed in good to excellent yields without applying column chromatography for purification.

Supporting Information



Publication History

Received: 18 October 2020

Accepted after revision: 10 November 2020

Article published online:
19 January 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany