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Open AccessArticle

An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms

by Xianhu Wei 1,2,3,4,5, Yanxia Ma 1,2,3,4,5, Qingping Wu 2,3,4,*, Jumei Zhang 2,3,4, Zhihe Cai 6 and Mianfei Lu 6
1
Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, China
2
State Key Laboratory of Applied Microbiology Southern China, Guangdong Institute of Microbiology, Guangzhou 510070, China
3
Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China
4
Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Institute of Microbiology, Guangzhou 510070, China
5
University of Chinese Academy of Sciences, Beijing 100039, China
6
Guangdong Huankai Microbial Sci. & Tech. Co., Ltd., Guangzhou 510663, China
*
Author to whom correspondence should be addressed.
Academic Editor: Vito Ferro
Molecules 2015, 20(12), 21681-21699; https://doi.org/10.3390/molecules201219789
Received: 15 September 2015 / Revised: 26 November 2015 / Accepted: 26 November 2015 / Published: 4 December 2015
An improved Helferich method is presented. It involves the glycosylation of 4-methyl-umbelliferone with glycosyl acetates in the presence of boron trifluoride etherate combined with triethylamine, pyridine, or 4-dimethylaminopyridine under mild conditions, followed by deprotection to give fluorogenic 4-methylumbelliferyl glycoside substrates. Due to the use of base, the glycosylation reaction proceeds more easily, is uncommonly α- or β-stereoselective, and affords the corresponding products in moderate to excellent yields (51%–94%) under appropriate conditions. View Full-Text
Keywords: fluorogenic substrates; 4-methylumbelliferyl glycosides; stereoselective glycosylation; glycosyl acetates; peracetyl sugars fluorogenic substrates; 4-methylumbelliferyl glycosides; stereoselective glycosylation; glycosyl acetates; peracetyl sugars
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MDPI and ACS Style

Wei, X.; Ma, Y.; Wu, Q.; Zhang, J.; Cai, Z.; Lu, M. An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms. Molecules 2015, 20, 21681-21699.

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