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Molecules 2015, 20(12), 21681-21699; doi:10.3390/molecules201219789

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

1,2,3,4,5
,
1,2,3,4,5
,
2,3,4,* , 2,3,4
,
6
and
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
Received: 15 September 2015 / Revised: 26 November 2015 / Accepted: 26 November 2015 / Published: 4 December 2015
View Full-Text   |   Download PDF [3723 KB, uploaded 4 December 2015]   |  

Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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