摘要 : Ozonolysis of peracetylated alpha-D-glucopyranosylprop-2-ene, followed by the reaction of the formed ozonide with (thiazol-2-yl)carbonylmethylenetriphenyl phosphorane, afforded substituted 1-oxa-1,3-butadiene, which by a hetero-Di... 展开 Ozonolysis of peracetylated alpha-D-glucopyranosylprop-2-ene, followed by the reaction of the formed ozonide with (thiazol-2-yl)carbonylmethylenetriphenyl phosphorane, afforded substituted 1-oxa-1,3-butadiene, which by a hetero-Diels-Alder reaction with ethyl vinyl ether gave a 1:1 mixture of two diastereoisomeric dihydropyran derivatives. These, after replacement of the acetyl protecting groups by benzyl groups, were separated by chromatography and their thiazole substituent converted to an aldehyde group. Subsequent hydroboration afforded alpha-C-(1 --> 3)-linked disaccharides in which D-glucose is linked by a methylene bridge with 2,3-dideoxy-arabino-hexopyranose of D- or L-configuration. Structures of the obtained compounds have been confirmed by NMR spectroscopy and X-ray crystallographic analysis. (C) 2004 Elsevier Ltd. All rights reserved. [References: 66] 收起