Regioselective Benzoylation of N-Protected D-Glucosamine |
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| Authors: | J Fuentes T Cuevas M A Pradera |
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| Institution: | Departamento de Química Orgánica, Facultad de Química , Universidad de Sevilla , Apartado 553, 41071, Sevilla, Spain |
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| Abstract: | Abstract Regioselective benzoylations of 2-deoxy-2-(2, 2-diethoxycarbonylvinyl) amino] -α-D-glucopyranose (1) yielded 6-mono-O- (2) 3, 6-di-O- (3), 4, 6-di-O- (4) and 1, 3, 6-tri-O-benzoyl- (5) derivatives. The fully benzoylated compound 6 was the major product when excess of benzoyl chloride was used. The di-O-acetyl derivatives (7 and 8) of 3 and 4 respectively were also prepared. The structures of 2-8 are based on analytical and/or spectroscopic data. Some data on MS fragmentation pathways of the partially protected compounds 2 and 4 are also reported. |
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