methyl 2,3-dideoxy-3-C-[(1R)-1-hydroxynonyl]-α-D-threo-pentofuranoside | 290347-31-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2,3-dideoxy-3-C-[(1R)-1-hydroxynonyl]-α-D-threo-pentofuranoside
• 英文别名: (1R)-1-[(2S,3S,5S)-2-(hydroxymethyl)-5-methoxyoxolan-3-yl]nonan-1-ol
• CAS: 290347-31-8
• 化学式: C₁₅H₃₀O₄
• 分子量: 274.401
• InChiKey: SGVVQEQPJDCARN-YJNKXOJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,3-dideoxy-3-C-[(1R)-1-hydroxynonyl]-α-D-threo-pentofuranoside 在 potassium permanganate 、 三氟化硼乙醚 、 sodium acetate 、 copper(II) sulfate 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 79.5h， 生成 (1S,5S,6R)-6-octyl-2,7-dioxabicyclo[3.3.0]octan-3,8-dione
  参考文献：
  名称：

  The Enantioselective Formal Synthesis of (+)-Avenaciolide and (+)-Isoavenaciolide from Tri-O-acetyl-D-glucal Using a Ring Contraction Reaction as the Key Step

  摘要：

  We describe a formal synthesis of (+)-avenaciolide and (+)-isoavenaciolide starting from methyl tri-O-acetyl-D-glucal. The key steps are a ring-contraction reaction of compound 8 to give the bicycle 6, and the oxidation of the diol 9 to the bis-lactone framework.

  DOI：

  10.1002/1099-0690(200006)2000:12<2285::aid-ejoc2285>3.0.co;2-8
• 作为产物：
  描述：

  1-溴辛烷 、 (+)-(1S,3S,5R,6R)-2,7-Dioxa-6-hydroxy-3-methoxybicyclo<3.3.0>octane 在 magnesium 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 methyl 2,3-dideoxy-3-C-[(1R)-1-hydroxynonyl]-α-D-threo-pentofuranoside 、 methyl 2,3-dideoxy-3-C-[(1S)-1-hydroxynonyl]-α-D-threo-pentofuranoside
  参考文献：
  名称：

  The Enantioselective Formal Synthesis of (+)-Avenaciolide and (+)-Isoavenaciolide from Tri-O-acetyl-D-glucal Using a Ring Contraction Reaction as the Key Step

  摘要：

  We describe a formal synthesis of (+)-avenaciolide and (+)-isoavenaciolide starting from methyl tri-O-acetyl-D-glucal. The key steps are a ring-contraction reaction of compound 8 to give the bicycle 6, and the oxidation of the diol 9 to the bis-lactone framework.

  DOI：

  10.1002/1099-0690(200006)2000:12<2285::aid-ejoc2285>3.0.co;2-8

文献信息

• The Enantioselective Formal Synthesis of (+)-Avenaciolide and (+)-Isoavenaciolide from Tri-O-acetyl-D-glucal Using a Ring Contraction Reaction as the Key Step
  作者：Eva Alcázar、Mohamed Kassou、Isabel Matheu、Sergio Castillón

  DOI：10.1002/1099-0690(200006)2000:12<2285::aid-ejoc2285>3.0.co;2-8

  日期：2000.6

  We describe a formal synthesis of (+)-avenaciolide and (+)-isoavenaciolide starting from methyl tri-O-acetyl-D-glucal. The key steps are a ring-contraction reaction of compound 8 to give the bicycle 6, and the oxidation of the diol 9 to the bis-lactone framework.