an improved helferich method for the α/β-stereoselective synthesis of 4-methylumbelliferyl glycosides for the detection of microorganisms
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ID: 168603
2015
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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.
| Reference Key |
wei2015moleculesan
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|---|---|
| Authors | ;Xianhu Wei;Yanxia Ma;Qingping Wu;Jumei Zhang;Zhihe Cai;Mianfei Lu |
| Journal | Journal of ethnopharmacology |
| Year | 2015 |
| DOI |
10.3390/molecules201219789
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| URL | |
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