Syntheses and reactions of saturated and 2,3-unsaturated vinyl and 1′-substituted-vinyl glycosides
作者:Anna de Raadt、Robert J. Ferrier
DOI:10.1016/0008-6215(92)84153-j
日期:1992.9
Abstract Reaction of tetra- O -α- d -glucopyranosyl bromide with bis(acylmethyl)mercurys [Hg (CH 2 COR) 2 ] afforded acetylated vinyl [by use of bis(formylmethyl)mercury] or 1′-substituted-vinyl β- d -glucopyranosides 11–13 in high yields. When used together with phenyl 4,6-di- O -acetyl-2,3-dideoxy-1-thio-α- d - erythro -hex-2-enopyranoside, these reagents gave analogous vinyl 4,6-di- O -acetyl-2
摘要四-O-α-d-吡喃葡萄糖基溴化物与双(酰基甲基)汞[Hg(CH 2 COR)2]反应,得到乙酰化的乙烯基[通过使用双(甲酰基甲基)汞]或1'-取代的乙烯基β- d-吡喃葡萄糖苷11-13高产。当与苯基4,6-二-O-乙酰基-2,3-二脱氧-1-硫代-α-d-赤-己基-2-烯吡喃糖苷一起使用时,这些试剂可得到类似的乙烯基4,6-二-O-乙酰-2,3-二脱氧-d-赤-己基-2-烯吡喃糖苷20-23,在用路易斯酸处理后,异构化为相应的C-糖基化合物,即(4,6-di-O-acetyl-2 ,3-dideoxy-d-赤型-hex-2-enopyranosy)乙醛(24,25)或相应的糖基化甲基酮26,27。制备C-3-支链糖的新途径涉及用双(苯甲酰基甲基)-汞处理上述硫代糖苷或不饱和乙烯基糖苷。