(-)-threo-methyl 2-methyl-3-hydroxyoctanate | 78604-72-5

• 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: (-)-threo-methyl 2-methyl-3-hydroxyoctanate
• 英文别名: Methyl (2R,3R)-3-Hydroxy-2-methyloctanoate
• CAS: 78604-72-5
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: HZYIMDGYVOETSV-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  7
• 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

• 作为产物：
  描述：

  (4R,5S)-3-<(2R,3S)-3-Hydroxy-2-methyloctanoyl>-4-methyl-5-phenyl-2-oxazolidinone 在 lithium hydroxide 、 双氧水 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 30.0h， 生成 (-)-threo-methyl 2-methyl-3-hydroxyoctanate
  参考文献：
  名称：

  Dolabellin, a Cytotoxic Bisthiazole Metabolite from the Sea Hare Dolabella auricularia: Structural Determination and Synthesis

  摘要：

  Dolabellin (1), a novel cytotoxic metabolite which consists of two thiazole hydroxy acids and a new dichlorinated beta-hydroxy acid, was isolated from the Japanese sea hare Dolabella auricularia. The gross structure of 1 was elucidated on the basis of spectral data in conjunction with chemical degradations, which provided three methyl esters: methyl 2-(1-hydroxy-2 -methylpropyl)thiazole-4-carboxylate (2), methyl 2-(1,2-dihydroxyethyl)thiazole-4-carboxylate (3), and methyl 7,7-dichloro-3-hydroxy-2-methyloctanoate (4). The absolute stereochemistry of 1 was determined by stereoselective syntheses of two degradation products 2 and 3 and two diastereomeric octanoates 7a,b (the dechloro derivatives of degradation product 4), and the enantioselective total synthesis of dolabellin itself. Dechlorodolabellin (23) was also synthesized.

  DOI：

  10.1021/jo00120a021

文献信息

• Stereoselectivity in the aldol reaction
  作者：A.I. Meyers、Yukio Yamamoto

  DOI：10.1016/0040-4020(84)80014-9

  日期：1984.1

  Chiral oxazolines, as their boron enolates derived from various boron triflates, react with aldehydes to give erythro-selectivity (97% + %) with enantiomeric purities of 50–60%. Achiral oxazolines as their boron enolates derived from diisopinocampheylborane give, on reaction with aldehydes, β-hydroxy esters with high threo-selectivity (90+%) in 77–85% ee. A variety of structurally different oxazolines

  手性恶唑啉是源自三氟甲磺酸三氟硼烷的硼烯酸酯，它与醛反应生成对映异构体纯度为50-60％的赤型选择性（97％+％）。非手性恶唑啉作为二异硫代樟脑硼烷的硼烯酸酯，与醛反应后，在77–85％ee中具有高苏式选择性（90％以上）的β-羟基酯。还研究了各种结构不同的恶唑啉，其中许多显示出高的赤型选择性。
• Enantioselective aldol reactions with high threo or erythro selectivity using boron azaenolates
  作者：A. I. Meyers、Yukio Yamamoto

  DOI：10.1021/ja00404a064

  日期：1981.7
• Enantioselective synthesis of anti-.alpha.-methyl-.beta.-hydroxy esters through titanium tetrachloride-mediated aldol condensation
  作者：Cesare Gennari、Anna Bernardi、Lino Colombo、Carlo Scolastico

  DOI：10.1021/ja00306a045

  日期：1985.10
• Watabu, Hisashi; Ohkubo, Munemasa; Matsubara, Hiroshi, Chemistry Letters, 1989, p. 2183 - 2184
  作者：Watabu, Hisashi、Ohkubo, Munemasa、Matsubara, Hiroshi、Sakai, Takashi、Tsuboi, Sadao、Utaka, Masanori

  DOI：——

  日期：——
• MEYERS, A. I.;YAMAMOTO, YUKIO, J. AMER. CHEM. SOC., 1981, 103, N 14, 4278-4279
  作者：MEYERS, A. I.、YAMAMOTO, YUKIO

  DOI：——

  日期：——