Methyl (2R,3S)-3-Hydroxy-2-methyloctanoate | 165522-03-2

• 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: Methyl (2R,3S)-3-Hydroxy-2-methyloctanoate
• CAS: 165522-03-2
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: HZYIMDGYVOETSV-BDAKNGLRSA-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 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 Methyl (2R,3S)-3-Hydroxy-2-methyloctanoate
  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

• 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
• Denmark Scott E., Griedel Brian D., Coe Diane M., Schnute Mark E., J. Amer. Chem. Soc., 116 (1994) N 16, S 7026-7043
  作者：Denmark Scott E., Griedel Brian D., Coe Diane M., Schnute Mark E.

  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：——
• Dolabellin, a Cytotoxic Bisthiazole Metabolite from the Sea Hare Dolabella auricularia: Structural Determination and Synthesis
  作者：Hiroki Sone、Takashi Kondo、Minoru Kiryu、Hiroyuki Ishiwata、Makoto Ojika、Kiyoyuki Yamada

  DOI：10.1021/jo00120a021

  日期：1995.7

  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.