Improved Synthesis of Sulfur-Containing Glycosides by Suppressing Thioacetyl Migration.
作者： Tao Luo , Ying Zhang , Jiafeng Xi , Yuchao Lu , Hai Dong
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摘要: Complex mixtures were often observed when we attempted to synthesize 4-thio- and 2,4-dithio-glycoside derivatives by double parallel serial inversion, thus leading no or low yields of target products. The reason was later found be that many unexpected side products produced a nucleophile substituted the leaving group on substrate containing thioacetate group. We hypothesized thioacetyl migration is prone occur due labile even under weak basic conditions caused nucleophile, this result. Therefore, managed inhibit generation thiol groups from addition an appropriate amount conjugate acid/anhydride, successfully improving synthesis derivatives. which previously difficult synthesize, herein obtained in relatively high yields. Finally, 4-deoxy- 2,4-dideoxy-glycoside efficiently synthesized through removal UV light, starting
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