The invention of radical reactions. Part XXXVIII. Homologation of car☐ylic acids with acrylamide and synthetic studies of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and its 4-epimer
作者:Derek H.R. Barton、Wansheng Liu
DOI:10.1016/s0040-4020(97)00543-7
日期:1997.8
Alkyl radicals generated from O-acyl derivatives of N-hydroxy-2-thiopyridone added onto acrylamide at room temperature to form crystalline 2-(2-pyridylsulfanyl)-car☐amides. Desulfurization of the latter by nickel boride at room temperature afforded primary amides in quantitative yield. 3-Deoxy-D-arabino-2-heptulosonic acid (DAH), its 4-epimer, and their derivatives were effectively synthesized from
由N-羟基-2-
硫代
吡啶酮的O-酰基衍
生物产生的烷基在室温下加到
丙烯酰胺上,形成结晶的2-(2-
吡啶基
硫烷基)-car☐酰胺。在室温下通过
硼化镍将后者脱
硫,以定量收率得到伯酰胺。通过类似的自由基
化学方法,从商业
D-核糖内酯有效合成了3-Deoxy-
D-阿拉伯糖-2-庚基
磺酸(
DAH),其4-表位及其衍
生物。