Synthesis and conformational studies on methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-hex-5-enopyranosides of the l series

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• 作者：Beata Liberek
• 关键词：Tosylation ; Iodination ; Hex-5-enopyranosides ; Enantiomers ; Anomeric effect ; Equatorial or axial orientation
• 刊名：Carbohydrate Research
• 出版年：2005
• 期刊代码：15_00086215
• 类别：ch
• 出版时间：2005
• 卷：340
• 期：12
• 页码：2039-2047
• 文件大小：181 K

摘要

Methyl 3-azido-2,3-dideoxy-α-d-xylo-, -α-d-lyxo-, and -β-d-xylo-hexopyranosides were converted into 4-O-acetyl-3-azido-6-iodo-2,3,6-trideoxy analogues via 6-O-p-tolylsulfonyl compounds. The elimination of hydrogen iodide from 6-iodo glycosides yielded methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-β-l-erythro-, -α-l-threo-, and -β-l-threo-hex-5-enopyranosides. The configuration and conformation of all products are evaluated in depth on the basis of ¹H and ¹³C NMR data. Factors determining conformational energy in 4-O-protected-3-azido-2,3,6,-trideoxy-hex-5-enopyranosides are discussed.