Direct vinylation of glucose derivatives with acetylene

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• 作者：Boris A. Trofimov ; Lidiya N. Parshina ; Ludmila A. Oparina ; Anatolii P. Tantsyrev ; Marina  ; Ya. Khil'ko ; Oksana V. Vysotskaya ; Andrey V. Stepanov ; Nina K. Gusarova ; Jochem Henkelmann
• 关键词：Glucose derivatives ; Acetylene ; Vinyl ethers ; Superbase catalytic systems
• 刊名：Tetrahedron
• 出版年：2007
• 出版时间：19 November 2007
• 年：2007
• 卷：63
• 期：47
• 页码：11661-11665
• 全文大小：209 K

文摘

Vinyl ethers, promising chiral carbohydrate synthons, have been synthesized by the addition of glucose acetals (1,2:5,6-di-O-isopropylidene-α-d-glucofuranose, methyl 4,6-O-benzylidene-α-d-glucopyranoside, 1,2-O-cyclohexylidene-α-d-glucofuranose, methyl α-d-glucopyranoside) to acetylene under atmospheric and elevated pressures in an autoclave in the presence of superbase catalytic systems (KOH–DMSO, t-BuOK–DMSO). The complete vinylation of 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose and methyl α-d-glucopyranoside has been realized under elevated pressure of acetylene in the system KOH–THF as well.