Regioselective synthesis of 4azido-Neu2en5,7Ac(2)1Me and its intramolecular transformation to 4azido-Neu2en5,9Ac(2)1Me |
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| Authors: | Zhao Qingjie Lou Yuanyuan Xiong Ruisheng Li Haihong Shen Jingshan |
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| Affiliation: | Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, PR China. |
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| Abstract: | Methyl 5-N-acetyl-7-O-acetyl-4-azido-2,3-didehydro-2,4-dideoxy-neuraminic acid (4azido-Neu2en5,7 Ac(2)1Me) was synthesized regioselectively starting from 4azido-Neu2en5Ac1Me in high yield. The transformation of 4azido-Neu2en5,7Ac(2)1Me to the corresponding thermodynamically stable 4azido-Neu2en5,9Ac(2)1Me via intramolecular acetyl migration was confirmed by single-crystal X-ray diffraction analysis. The proposed rearrangement mechanism is discussed. |
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| Keywords: | Neu5Ac Analogues Acetyl migration Azides X-ray crystal structure Carbohydrates |
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