ethyl threo(2S,3S)-3-chloro-2-hydroxyoctanoate | 108682-82-2

• 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 threo(2S,3S)-3-chloro-2-hydroxyoctanoate
• 英文别名: Ethyl (2S,3S)-3-chloro-2-hydroxyoctanoate
• CAS: 108682-82-2
• 化学式: C₁₀H₁₉ClO₃
• 分子量: 222.712
• InChiKey: HIXWIGOAQAVRGM-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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 threo(2S,3S)-3-chloro-2-hydroxyoctanoate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以85%的产率得到(2S,3S)-3-chloro-1,2-octanediol
  参考文献：
  名称：

  (2R,3S)-2,3-环氧辛醛的不对称合成，14,15-白三烯A4的关键中间体

  摘要：

  用面包酵母不对称还原 3-氯-2-氧代辛酸乙酯得到 3-氯-2-羟基辛酸乙酯 (3) [(2S,3R)/(2S,3S), 4:1]，产率 67%，>99 % ee 氯醇(2S,3R)-3通过依次还原、脱氯化氢和氧化以34%的总产率转化为标题化合物，其中80% ee。(2R,3R)2,3-环氧辛醛也由 (2S,3S)-3 制备，总产率为 33%，ee 为 94%

  DOI：

  10.1246/bcsj.60.833
• 作为产物：
  描述：

  Ethyl 2-chloro-3-pentyloxirane-2-carboxylate 在 aluminum oxide 、 sodium tetrahydroborate 作用下， 以 乙醇 、 xylene 为溶剂， 反应 3.17h， 生成 ethyl threo(2S,3S)-3-chloro-2-hydroxyoctanoate
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates. Its application for the synthesis of (−)-disparlure

  摘要：

  Reduction of 3-chloro-2-oxoalkanoates 1 with NaBH4 gave predominantly syn-3-chloro-2-hydroxyalkanoates 2 (synlanti=91/9-99/1) in 50-97% yields. Resolution of syn-2 by lipase-catalyzed transesterification gave (2S,3S)-2 and (2R,3R)-2-acetoxy-3-chloroalkanoates (2R,3R)-3. Total synthesis of (-)-disparlure, the pheromone of the gypsy moth was established from (2S,3S)-2g via 4 steps in 34.9% overall yield. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(96)00529-0

文献信息

• Asymmetric Synthesis of (2<i>R</i>,3<i>S</i>)-2,3-Epoxyoctanal, a Key Intermediate of 14,15-Leukotriene A₄
  作者：Sadao Tsuboi、Hiroyuki Furutani、Akira Takeda

  DOI：10.1246/bcsj.60.833

  日期：1987.2

  Asymmetric reduction of ethyl 3-chloro-2-oxooctanoate with baker’s yeast gave ethyl 3-chloro-2-hydroxyoctanoate (3) [(2S,3R)/(2S,3S), 4:1] in 67% yield with >99% e.e. Chlorohydrin (2S,3R)-3 was converted to the titled compound in 34% total yield with 80% e.e. via the reduction, dehydrochlorination, and oxidation, successively. (2R,3R)2,3-Epoxyoctanal was also prepared from (2S,3S)-3 in 33% total yield

  用面包酵母不对称还原 3-氯-2-氧代辛酸乙酯得到 3-氯-2-羟基辛酸乙酯 (3) [(2S,3R)/(2S,3S), 4:1]，产率 67%，>99 % ee 氯醇(2S,3R)-3通过依次还原、脱氯化氢和氧化以34%的总产率转化为标题化合物，其中80% ee。(2R,3R)2,3-环氧辛醛也由 (2S,3S)-3 制备，总产率为 33%，ee 为 94%
• 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.
• 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：——
• Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates. Its application for the synthesis of (−)-disparlure
  作者：Sadao Tsuboi、Nobuyuki Yamafuji、Masanori Utaka

  DOI：10.1016/s0957-4166(96)00529-0

  日期：1997.2

  Reduction of 3-chloro-2-oxoalkanoates 1 with NaBH4 gave predominantly syn-3-chloro-2-hydroxyalkanoates 2 (synlanti=91/9-99/1) in 50-97% yields. Resolution of syn-2 by lipase-catalyzed transesterification gave (2S,3S)-2 and (2R,3R)-2-acetoxy-3-chloroalkanoates (2R,3R)-3. Total synthesis of (-)-disparlure, the pheromone of the gypsy moth was established from (2S,3S)-2g via 4 steps in 34.9% overall yield. (C) 1997 Elsevier Science Ltd. All rights reserved.
• 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