Ethyl (2S,3R)-3-chloro-2-hydroxytridecanoate | 113566-29-3

• 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: Ethyl (2S,3R)-3-chloro-2-hydroxytridecanoate
• 英文别名: 3R-Chloro-2S-hydroxy-tridecanoic acid ethyl ester
• CAS: 113566-29-3
• 化学式: C₁₅H₂₉ClO₃
• 分子量: 292.846
• InChiKey: WLMKNFZJIDSQJJ-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl (2S,3R)-3-chloro-2-hydroxytridecanoate 在 sodium tetrahydroborate 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 19.5h， 生成 [(2R,3R)-3-丙基-2-环氧乙烷基]甲醇
  参考文献：
  名称：

  Highly enantioselective reduction of 3-chloro-2-oxoalkanoates with fermenting bakers' yeast. A new synthesis of optically active 3-chloro-2-hydroxyalkanoates and glycidic esters

  摘要：

  Reduction of 3-chloro-2-oxoalkanoic esters with fermenting bakers' yeast gave optically active 3-chloro-2-hydroxyalkanoic esters 2 (anti(2S,3R)/syn (2S,3S) = 52:48-90:10) in 50-85% yields with >95% ee except for 43% ee of ethy syn-(2S,3S)-3-chloro-2-hydroxy-4 phenylbutanoate (2j). Compounds 2 were treated with NaOEt to give (E)-(2R,3S)-2,3-epoxyalkanoates 3 in 30-66% yields with 44-64% ee. Optically active 2,3-epoxy alcohols (cis-23, trans-23, and trans-25), key intermediates for the syntheses of (-)-disparlure (4), mosquito pheromone (5), and a component of passion fruit flavor (6), were prepared with more than 86% ee in high yields.

  DOI：

  10.1021/jo00054a036
• 作为产物：
  描述：

  ethyl 3-chloro-2-oxotridecanoate 在 potassium dihydrogenphosphate 、 葡萄糖 、 raw baker's yeast (Oriental) 、 magnesium sulfate 、 calcium carbonate 作用下， 以 水 为溶剂， 反应 72.0h， 生成 Ethyl (2S,3R)-3-chloro-2-hydroxytridecanoate 、 (2S,3S)-ethyl 3-chloro-2-hydroxytridecanoate
  参考文献：
  名称：

  A Practical Synthesis of Chiral 3-Chloro-2-hydroxyalkanoates and 2,3-Epoxyalcohols

  摘要：

  DOI：

  10.1016/s0040-4039(00)96187-2

文献信息

• A Practical Synthesis of Chiral 3-Chloro-2-hydroxyalkanoates and 2,3-Epoxyalcohols
  作者：Sadao Tsuboi、Hiroyuki Furutani、Masanori Utaka、Akira Takeda

  DOI：10.1016/s0040-4039(00)96187-2

  日期：1987.1
• TSUBOI, SADAO;FURUTANI, HIROYUKI;UTAKA, MASANORI;TAKEDA, AKIRA, TETRAHEDRON LETT., 28,(1987) N 24, 2709-2712
  作者：TSUBOI, SADAO、FURUTANI, HIROYUKI、UTAKA, MASANORI、TAKEDA, AKIRA

  DOI：——

  日期：——
• Highly enantioselective reduction of 3-chloro-2-oxoalkanoates with fermenting bakers' yeast. A new synthesis of optically active 3-chloro-2-hydroxyalkanoates and glycidic esters
  作者：Sadao Tsuboi、Hiroyuki Furutani、Mohammad Hafeez Ansari、Takashi Sakai、Masanori Utaka、Akira Takeda

  DOI：10.1021/jo00054a036

  日期：1993.1

  Reduction of 3-chloro-2-oxoalkanoic esters with fermenting bakers' yeast gave optically active 3-chloro-2-hydroxyalkanoic esters 2 (anti(2S,3R)/syn (2S,3S) = 52:48-90:10) in 50-85% yields with >95% ee except for 43% ee of ethy syn-(2S,3S)-3-chloro-2-hydroxy-4 phenylbutanoate (2j). Compounds 2 were treated with NaOEt to give (E)-(2R,3S)-2,3-epoxyalkanoates 3 in 30-66% yields with 44-64% ee. Optically active 2,3-epoxy alcohols (cis-23, trans-23, and trans-25), key intermediates for the syntheses of (-)-disparlure (4), mosquito pheromone (5), and a component of passion fruit flavor (6), were prepared with more than 86% ee in high yields.