Photo-oxygenation of glycosylfurans. Rearrangement of C-glycosyl into O-glycosyl derivatives
作者:F.J. Lopez Aparicio、J.A. Lopez Sastre、J. Isac Garcia、R. Robles Diaz
DOI:10.1016/0008-6215(84)85060-0
日期:1984.9
-isopropylidene-β- d -erythrofuranosyl 3-acetyl-3-hydroxymethylacrylate, respectively. The endo -peroxides can be reduced without rearrangement, yielding C -glycosyl derivatives. Alcoholysis of the O -glycosyl derivatives yields 2,3- O -isopropylidene- d -erythrose, dialkyl 2-acetyl-3-alkoxysuccinates, 4-ethoxycarbonyl-5-methoxy-5-methyl-2-oxo-2,5-dihydrofuran and 4-hydroxymethyl-5-methoxy-5-methyl-2-oxo-2,5-dihydrofuran
摘要对3-乙氧基羰基-5-(2,3-O-异亚丙基-β-d-异呋喃呋喃糖基)-2-甲基呋喃和3-羟甲基-5-(2,3-O-异亚丙基-β-d-进行光氧化赤藓呋喃糖基)-2-甲基呋喃产生相应的内-过氧化物,其在室温下重排成O-糖基衍生物乙基2-3-O-异亚丙基-β-d-2-呋喃呋喃糖基2-乙酰基富马酸酯和2,3-O-异亚丙基-β -分别为3-乙酰基-3-乙酰基-3-羟基甲基丙烯酸-d-呋喃呋喃糖基。可以减少内过氧化物而不进行重排,产生C-糖基衍生物。O-糖基衍生物的醇解得到2,3-O-异亚丙基-d-赤藓糖,2-乙酰基-3-烷氧基琥珀酸二烷基酯,4-乙氧基羰基-5-甲氧基-5-甲基-2-甲基-2-氧代-2,5-二氢呋喃和4-羟甲基-5-甲氧基-5-甲基-2-氧代-2,5-二氢呋喃。