Organofluorine compounds and fluorinating agents Part 21: Perfluoroalkylidene sugars by non-classical acetalation of pyranoses

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• 作者：Zur ; Cornelia ; Miller ; Alexey O. ; Miethchen ; Ralf
• 关键词：Carbohydrates ; d-Altrose ; d-Gulose ; Perfluoroalkanals ; Perfluoroalkylidene Acetals ; Fluorosurfactants ; Liquid Crystals
• 刊名：Journal of Fluorine Chemistry
• 出版年：1998
• 出版时间：June 26, 1998
• 年：1998
• 卷：90
• 期：1
• 页码：67-76
• 全文大小：840 K

文摘

Acetalations of methyl α-d-mannopyranoside (1), methyl 6-O-trityl-α-d-mannopyranoside (5), benzyl α-d-mannopyranoside (14), and methyl β-d-galactopyranoside (17) with perfluoroaldehydes (C₄F₉CH=O, C₆F₁₃CH=O, and C₈F₁₇CH=O) in the presence of dicyclohexylcarbodiimide (DCC) lead, under epimerization at the C-atom 3 of the corresponding pyranose moiety, to perfluoroalkylidene derivatives of α-d-altrosides (2-4,, 15) and of β-d-gulosides (18-20), respectively. After partial deprotection of 3 (or 15) and 18-20, respectively, the liquid crystalline, amphiphilic 3,4-O-perfluorohexylidene-d-altropyranoside (13) and 2,3-O-perfluoroalkylidene-d-gulopyranosides 24-26 were obtained.