3-Desoxy-D-galactono-γ-lacton | 134524-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-Desoxy-D-galactono-γ-lacton
• 英文别名: (3R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3-hydroxyoxolan-2-one
• CAS: 134524-29-1
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: NSEFGBGANVMEIR-MROZADKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-甘露糖酸-1,4-内酯 在 palladium on activated charcoal ammonium formate 、 sodium hydride 作用下， 以 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 26.0h， 生成 3-Desoxy-D-galactono-γ-lacton
  参考文献：
  名称：

  A two step synthesis of 3-deoxy-d- or l-glycono-1,4-lactones and 2-0-alkyl-3-deoxy-d-glycono-1,4-lactones from d- or l-glyconolactones

  摘要：

  Treatment of unprotected D-or L-glyconolactones with sodium hydride and alkyl halides, in dimethylsulfoxide, led to the corresponding 2-O-alkyl-3-deoxy-2-enono-1,4-lactones. Hydrogenolysis of 2-O-benzyl derivatives by catalytic hydrogen transfer with palladium on charcoal and cyclohexene as hydrogen donor gave 3-deoxy-hex- or pent-2-enono-1,4-lactones in the enolic forms. Reduction of 2-O-benzyl-enonolactones with ammonium formate as hydrogen donor afforded 3-deoxy-D- or L-glycono-1,4-lactones when 2-O-alkyl ethers gave the corresponding ethers. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00164-x

文献信息

• Bock, Klaus; Lundt, Inge; Pedersen, Christian, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 3, p. 155 - 162
  作者：Bock, Klaus、Lundt, Inge、Pedersen, Christian

  DOI：——

  日期：——
• A two step synthesis of 3-deoxy-d- or l-glycono-1,4-lactones and 2-0-alkyl-3-deoxy-d-glycono-1,4-lactones from d- or l-glyconolactones
  作者：Caroline Choquet-Farnier、Imane Stasik、Daniel Beaupère

  DOI：10.1016/s0008-6215(97)00164-x

  日期：1997.9

  Treatment of unprotected D-or L-glyconolactones with sodium hydride and alkyl halides, in dimethylsulfoxide, led to the corresponding 2-O-alkyl-3-deoxy-2-enono-1,4-lactones. Hydrogenolysis of 2-O-benzyl derivatives by catalytic hydrogen transfer with palladium on charcoal and cyclohexene as hydrogen donor gave 3-deoxy-hex- or pent-2-enono-1,4-lactones in the enolic forms. Reduction of 2-O-benzyl-enonolactones with ammonium formate as hydrogen donor afforded 3-deoxy-D- or L-glycono-1,4-lactones when 2-O-alkyl ethers gave the corresponding ethers. (C) 1997 Elsevier Science Ltd.