Synthesis of C-glycopyranosylfuran derivatives by reaction of dialdehydes with cyanoacetamide
作者:F.J. Lopez Aparicio、F. Santoyo Gonzalez、P. Garcia Mendoza、J.A. Dominguez Martinez
DOI:10.1016/s0008-6215(00)90634-7
日期:1986.3
Abstract The reaction of diglycol- and thiodiglycol-aldehyde ( 1a,b ) with cyanoacetamide yields cis -3,5-diacetoxy-4-carbamoyl-4-cyano-tetrahydropyran ( 2a ) and -tetrahydrothiopyran ( 2b ). When this reaction is applied to (2 S )-2-(3-ethoxycarbonyl-2-methyl-5-furyl)-3,5-dihydroxy-1,4-dioxane ( 1c ), (2 S )-3,5-dihydroxy-2-(3-methoxycarbonyl-2-methyl-5-furyl)-1,4-dioxane ( 1d ), and (2 S ,3 R ,5
摘要二甘醇和硫代二甘醇-醛(1a,b)与氰基乙酰胺的反应生成顺-3,5-二乙酰氧基-4-氨基甲酰基-4-氰基四氢吡喃(2a)和-四氢噻喃(2b)。当该反应应用于(2 S)-2-(3-乙氧基羰基-2-甲基-5-呋喃基)-3,5-二羟基-1,4-二恶烷(1c),(2 S)-3,5 -二羟基-2-(3-甲氧基羰基-2-甲基-5-呋喃基)-1,4-二恶烷(1d)和(2 S,3 R,5 S)-2-(3-乙酰基-2-甲基-5-呋喃基)-3,5-二羟基-1,4-二恶烷(1e),5-(3-氨基甲酰基-3-氰基-3-脱氧-β-d-木基-戊吡喃糖基)-3-乙氧基羰基-2 -甲基呋喃(2c),5-(2,4-二-O-乙酰基-3-氨基甲酰基-3-氰基-3-脱氧-β-d-木基-戊吡喃糖基)-3-甲氧基羰基-2-甲基呋喃(2e)分别是3-乙酰基-5-(2,4-二-O-乙酰基-3-氨基甲酰基-3-氰基-3-脱氧-β-d-