2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl cyanide | 130495-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl cyanide
• 英文别名: (1R,2R,6R,7R,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecane-7-carbonitrile
• CAS: 130495-49-7
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: NVQPONDMQLISHZ-ISUQUUIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甘露糖 在 2-氟-1-甲基吡啶翁对甲苯磺酸盐 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 115.0h， 生成 2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl cyanide
  参考文献：
  名称：

  C-Glycoside syntheses. 1. Glycosyl cyanides and isocyanides from glycosyl fluorides with full acetal protection

  摘要：

  2,3:5,6-Di-O-isopropylidenemannofuranose, 2,3:4,6-di-O-isopropylidenemannopyranose, and 2,3,4,6-tetra-O-benzylglucopyranose each have been converted with 2-fluoro-1-methylpyridinium tosylate into anomerically pure pairs of glycosyl fluorides. Reaction of each anomeric mannopyranosyl and mannofuranosyl fluoride with Et2AlCN in THF gave only the two (four component) anomeric mixtures of mannopyranosyl, respectively mannofuranosyl cyanides and isocyanides. The pyranosidic four component mixture (alpha-CN, alpha-NC, beta-CN, and beta-NC) was completely separated by a combination of flash chromatography, crystallization, and/or preparative HPLC to give the individual components; in the furanose series, only the crystalline two component mixture of alpha-furano cyanide and isocyanide could not be resolved. Isocyanides show two absorption maxima in their UV spectra (195 and 230 nm) while cyanides show only the first. Cyanides, being C-glycosides, char more slowly on heated TLC plates than isocyanides.

  DOI：

  10.1021/jo00002a007

文献信息

• C-Glycoside syntheses. 1. Glycosyl cyanides and isocyanides from glycosyl fluorides with full acetal protection
  作者：Kenneth N. Drew、Paul H. Gross

  DOI：10.1021/jo00002a007

  日期：1991.1

  2,3:5,6-Di-O-isopropylidenemannofuranose, 2,3:4,6-di-O-isopropylidenemannopyranose, and 2,3,4,6-tetra-O-benzylglucopyranose each have been converted with 2-fluoro-1-methylpyridinium tosylate into anomerically pure pairs of glycosyl fluorides. Reaction of each anomeric mannopyranosyl and mannofuranosyl fluoride with Et2AlCN in THF gave only the two (four component) anomeric mixtures of mannopyranosyl, respectively mannofuranosyl cyanides and isocyanides. The pyranosidic four component mixture (alpha-CN, alpha-NC, beta-CN, and beta-NC) was completely separated by a combination of flash chromatography, crystallization, and/or preparative HPLC to give the individual components; in the furanose series, only the crystalline two component mixture of alpha-furano cyanide and isocyanide could not be resolved. Isocyanides show two absorption maxima in their UV spectra (195 and 230 nm) while cyanides show only the first. Cyanides, being C-glycosides, char more slowly on heated TLC plates than isocyanides.