An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms
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 fluorogeni...
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MDPI AG
2015-12-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/12/19789 |
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doaj-2c86b38121894d96af900a7097dcf6b82020-11-24T23:01:32ZengMDPI AGMolecules1420-30492015-12-012012216812169910.3390/molecules201219789molecules201219789An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of MicroorganismsXianhu Wei0Yanxia Ma1Qingping Wu2Jumei Zhang3Zhihe Cai4Mianfei Lu5Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, ChinaGuangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, ChinaState Key Laboratory of Applied Microbiology Southern China, Guangdong Institute of Microbiology, Guangzhou 510070, ChinaState Key Laboratory of Applied Microbiology Southern China, Guangdong Institute of Microbiology, Guangzhou 510070, ChinaGuangdong Huankai Microbial Sci. & Tech. Co., Ltd., Guangzhou 510663, ChinaGuangdong Huankai Microbial Sci. & Tech. Co., Ltd., Guangzhou 510663, ChinaAn 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.http://www.mdpi.com/1420-3049/20/12/19789fluorogenic substrates4-methylumbelliferyl glycosidesstereoselective glycosylationglycosyl acetatesperacetyl sugars |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Xianhu Wei Yanxia Ma Qingping Wu Jumei Zhang Zhihe Cai Mianfei Lu |
| spellingShingle |
Xianhu Wei Yanxia Ma Qingping Wu Jumei Zhang Zhihe Cai Mianfei Lu An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms Molecules fluorogenic substrates 4-methylumbelliferyl glycosides stereoselective glycosylation glycosyl acetates peracetyl sugars |
| author_facet |
Xianhu Wei Yanxia Ma Qingping Wu Jumei Zhang Zhihe Cai Mianfei Lu |
| author_sort |
Xianhu Wei |
| title |
An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms |
| title_short |
An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms |
| title_full |
An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms |
| title_fullStr |
An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms |
| title_full_unstemmed |
An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms |
| title_sort |
improved helferich method for the α/β-stereoselective synthesis of 4-methylumbelliferyl glycosides for the detection of microorganisms |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2015-12-01 |
| description |
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. |
| topic |
fluorogenic substrates 4-methylumbelliferyl glycosides stereoselective glycosylation glycosyl acetates peracetyl sugars |
| url |
http://www.mdpi.com/1420-3049/20/12/19789 |
| work_keys_str_mv |
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