A diastereoselective C-C bond formation at C-5 of d-gulose. A convenient approach to (5S)-5-C-alkyl-尾-l-lyxo-hexofuranoses

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• 作者：Jozef Gonda ; D谩vid Mali艌谩k ; Margar茅ta Kov谩膷ov谩 ; Miroslava Martinkov谩 ; Martin Walko
• 刊名：Tetrahedron: Asymmetry
• 出版年：15 December, 2013
• 年：2013
• 卷：24
• 期：23
• 页码：1514-1519
• 全文大小：631 K

文摘

A flexible approach to the stereoselective synthesis of (5S)-5-C-methyl- and (5S)-5-C-ethyl-尾-l-lyxo-hexofuranoses dFont">15a, dFont">22 starting from 1,2:5,6-di-O-isopropylidene-伪-d-gulofuranose dFont">3 as the source of chirality is described. The corresponding C-5 alkyl groups were introduced via a Wittig olefination followed by Pd/C-mediated hydrogenation of the conformationally restricted alkenes in a highly diastereoselective manner.