1,3,4,6-tetra-O-acetyl-2,5-anhydro-D-glucitol | 42400-20-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2,5-anhydro-D-glucitol
• 英文别名: 2,5-Anhydro-D-mannitol Tetraacetate；(2R,3R,4R,5R)-2,5-bis(acetoxymethyl) tetrahydrofuran-3,4-diyldiacetate；(2R,3R,4S,5S)-2,5-bis(acetoxymethyl)-3,4-bis(acetoxy)tetrahydrofuran；1,3,4,6-tetra-O-acetyl-2,5-anhydrogalactitol；acetylated-2,5-anhydro-D-mannose
• CAS: 42400-20-4；65729-86-4；65729-88-6；74743-76-3；74743-82-1；80656-75-3；82730-65-2
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: LRVQZSOYVOEEPQ-ZXCYLUJYSA-N

物化性质

• 沸点：
  405.3±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  乙酸酐 、 (3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-carbaldehyde 生成 1,3,4,6-tetra-O-acetyl-2,5-anhydro-D-glucitol
  参考文献：
  名称：

  Chemistry of glucal halohydrins(II): An unusual protecting group effect in the competitive formation of formyl furanosides and methyl glycosides

  摘要：

  A remarkable protecting group influence was observed in the base-induced reaction of protected halohydrins derived from D-glycals. Tri-O-methyl and tri-O-benzyl halohydrins react with cesium carbonate in methanol at room temperature to give methyl glycosides as the major product and unsaturated formyl furanosides as the minor product. Whereas, the tri-O-tert-butyldimethylsilyl (t-BuMe2Si)-protected halohydrins reacted with cesium carbonate in methanol at room temperature to give a mixture of epimeric formyl furanosides, and at reflux to give an unsaturated formyl furanoside, as the only products. The tri-O-methyl and tri-O-benzyl halohydrins react slowly at elevated temperature to give predominantly furans. In comparison, the tri-O-t-BuMe2Si halohydrins reacted completely after five minutes to give a mixture of epimeric formyl furanosides. The tri-O-t-BuMe2Si iodohydrins were oxidized to the corresponding iodolactones, which also underwent a based-induced ring contraction in methanol to give the furanose 1-methylcarboxylate esters. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00054-2

文献信息

• Preparation of acetylated derivatives of modified chito-oligosaccharides by the depolymerisation of partially N-acetylated chitosan with nitrous acid
  作者：Shigehiro Hirano、Yōtaro Kondo、Kunio Fujii

  DOI：10.1016/s0008-6215(00)90682-7

  日期：1985.12