2-O-benzoyl-3-deoxy-5,6-O-isopropylidene-D-threo-hex-2-enono-1,4-lactone | 172603-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-O-benzoyl-3-deoxy-5,6-O-isopropylidene-D-threo-hex-2-enono-1,4-lactone
• 英文别名: [(2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-oxo-2H-furan-4-yl] benzoate
• CAS: 172603-51-9
• 化学式: C₁₆H₁₆O₆
• 分子量: 304.299
• InChiKey: HDTXNSCDAHVYOO-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-O-benzoyl-3-deoxy-5,6-O-isopropylidene-D-threo-hex-2-enono-1,4-lactone 在 盐酸 、 碳酸氢钠 作用下， 生成 sodium 3-deoxy-α-D-threo-hex-2-ulo-pyranosonate 、 sodium 3-deoxy-β-D-threo-hex-2-ulo-pyranosonate 、 sodium 3-deoxy-β-D-threo-hex-2-ulo-furanosonate 、 sodium 3-deoxy-α-D-threo-hex-2-ulo-furanosonate
  参考文献：
  名称：

  β-elimination of protected aldono-1,4-lactones as a general approach to the synthesis of 2-keto-3-deoxyaldonic acids containing four to six carbon atoms

  摘要：

  The well-known beta-elimination of protected aldonolactones is used for the synthesis of the short-chain 2-keto-3-deoxyaldonic acids 1-4 containing four to six carbon atoms. The key step is the facile beta-elimination step which generates the desired 2-keto-3-deoxy acids as protected enol 1,4-lactones in excellent yields. Smooth deprotection then leads to the 2-keto-3-deoxyaldonic acids. In the case of the protected D-galactono-1,4-lactone 6 an epimerisation is observed during the elimination process. This enables the synthesis of both 2-keto-3-deoxy-D-hexonic acids with either D-erythro (1) or D-threo (2) configuration in good to excellent yields in only three steps starting with commercially available D-galactono-1,4-lactone (5).

  DOI：

  10.1016/0008-6215(95)00124-c
• 作为产物：
  描述：

  D-半乳糖酸-1,4-内酯 在 吡啶 、 Amberlite IR-120 (H⁺) 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 44.0h， 生成 2-O-benzoyl-3-deoxy-5,6-O-isopropylidene-D-threo-hex-2-enono-1,4-lactone
  参考文献：
  名称：

  β-elimination of protected aldono-1,4-lactones as a general approach to the synthesis of 2-keto-3-deoxyaldonic acids containing four to six carbon atoms

  摘要：

  The well-known beta-elimination of protected aldonolactones is used for the synthesis of the short-chain 2-keto-3-deoxyaldonic acids 1-4 containing four to six carbon atoms. The key step is the facile beta-elimination step which generates the desired 2-keto-3-deoxy acids as protected enol 1,4-lactones in excellent yields. Smooth deprotection then leads to the 2-keto-3-deoxyaldonic acids. In the case of the protected D-galactono-1,4-lactone 6 an epimerisation is observed during the elimination process. This enables the synthesis of both 2-keto-3-deoxy-D-hexonic acids with either D-erythro (1) or D-threo (2) configuration in good to excellent yields in only three steps starting with commercially available D-galactono-1,4-lactone (5).

  DOI：

  10.1016/0008-6215(95)00124-c

文献信息

• β-elimination of protected aldono-1,4-lactones as a general approach to the synthesis of 2-keto-3-deoxyaldonic acids containing four to six carbon atoms
  作者：Gerrit Limberg、Joachim Thiem

  DOI：10.1016/0008-6215(95)00124-c

  日期：1995.9

  The well-known beta-elimination of protected aldonolactones is used for the synthesis of the short-chain 2-keto-3-deoxyaldonic acids 1-4 containing four to six carbon atoms. The key step is the facile beta-elimination step which generates the desired 2-keto-3-deoxy acids as protected enol 1,4-lactones in excellent yields. Smooth deprotection then leads to the 2-keto-3-deoxyaldonic acids. In the case of the protected D-galactono-1,4-lactone 6 an epimerisation is observed during the elimination process. This enables the synthesis of both 2-keto-3-deoxy-D-hexonic acids with either D-erythro (1) or D-threo (2) configuration in good to excellent yields in only three steps starting with commercially available D-galactono-1,4-lactone (5).