Synthesis of S-linked carbohydrate analogues via a Ferrier reaction

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• 作者：David Ellis ; Sarah E. Norman ; Helen M.I. Osborn
• 关键词：Cyclodipeptides ; 3-[(Indol-3-yl)methylidene]piperazine-2 ; 5-dione ; Enaminones ; Indoles ; Copper(I) catalyzed coupling ; Natural products
• 刊名：Tetrahedron
• 出版年：2008
• 出版时间：17 March 2008
• 年：2008
• 卷：64
• 期：12
• 页码：2832-2854
• 全文大小：1191 K

文摘

In this work, the synthetic utility of the Ferrier reaction to access S-linked disaccharides and S-linked glycoamino acids has been probed. Significantly, entry to a range of 1,4- and 1,6-S-linked disaccharides has been achieved using glycals derived from glucose and galactose, and sulfur containing coupling partners derived from methyl α-lass=""smCaps"">d-glucopyranoside. Access to S-linked glycoamino acids and glycopeptides has also been achieved using protected cysteine and homocysteine coupling partners within the Ferrier reaction. Functionalisation of the Ferrier products, for example, via dihydroxylation using OsO₄ or amino acid coupling, and deprotection of the targets have also been achieved. In this way, entry to materials of interest as mimics of biologically interesting disaccharides and glycopeptides has been realised, including targets derived from rare sugars such as talopyranose and gulopyranose.