Use of Acyclic Glycosyl Donors for Furanoside Synthesis
Use of Acyclic Glycosyl Donors for Furanoside Synthesis
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DOI：
10.1021/jo9618583
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发表时间：
1997-03
影响因子：
3.6
通讯作者：
J. Mcauliffe;O. Hindsgaul
中科院分区：
文献类型：
--
作者：
J. Mcauliffe;O. Hindsgaul
用乙酰氯和三氟化硼乙醚合物在回流下处理d-葡萄糖、d-半乳糖和d-甘露糖的全乙酰化乙基二硫代缩醛，得到已知的无环1-氯-1-（乙硫基）衍生物。这些化合物显示出使用三氟甲磺酸银作为促进剂有效地糖基化各种碳水化合物受体，以良好至优异的产率立体特异性地提供相应的无环O，S-缩醛。此外，脱乙酰化后，用汞盐在甲醇或二甲基甲酰胺中的混合物处理这些O，S-缩醛，产生以d-呋喃糖基残基终止的二糖。
Treatment of the peracetylated ethyl dithioacetals of d-glucose, d-galactose, and d-mannose with acetyl chloride and boron trifluoride diethyl etherate at reflux yields the known acyclic 1-chloro-1-(ethylthio) derivatives. These compounds are shown to effectively glycosylate a variety of carbohydrate acceptors using silver trifluoromethanesulfonate as the promotor, affording stereospecifically the corresponding acyclic O,S-acetals in good to excellent yield. Furthermore, following deacetylation, treatment of these O,S-acetals with a mixture of mercuric salts in either methanol or dimethylformamide gives rise to disaccharides terminating in d-furanosyl residues.