ethyl (2S,3R)-3-hydroxy-2,4,4-trimethylpentanoate | 155320-80-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl (2S,3R)-3-hydroxy-2,4,4-trimethylpentanoate
• CAS: 155320-80-2
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: UUZSZHDFNAQHDQ-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  5
• 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 (2S,3R)-3-hydroxy-2,4,4-trimethylpentanoate 、 氢化铝锂 生成 2,4,4-trimethylpentane-1,3-diol
  参考文献：
  名称：

  DERBALI, Y., J. SOC. CHIM. TUNIS, 2,(1988) N 7, C. 9-16

  摘要：

  DOI：
• 作为产物：
  描述：

  丙酸乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 (S)-4-Isopropyl-3-tosyl-[1,3,2]oxazaborolidin-5-one 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 ethyl (2S,3R)-3-hydroxy-2,4,4-trimethylpentanoate
  参考文献：
  名称：

  A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions

  摘要：

  A shortening of the reaction path can be realized by using a series of the chiral oxazaborolidinone-promoted aldol reaction with respect to the practical synthesis of the (+)-acutiphycin seco acid derivative 5. The linear strategy is based on the utilization of five aldol reactions with a sequence of silyl nucleophiles, 7, 8, 35, 10, and 11, in the presence of stoichiometric amounts of the promoter, 1 or 2. The construction of the relative configuration between the stereogenic centers is diastereoselectively controlled by the stereochemistry of the promoter used in the enantioselective aldol reaction, which is nearly independent of that of the substrate (promoter control).

  DOI：

  10.1021/jo990342r

文献信息

• Chelation-controlled protocol for the diastereoselective reduction of ketones
  作者：Christopher R. Sarko、Ian C. Guch、Marcello DiMare

  DOI：10.1021/jo00083a004

  日期：1994.2

  A new chelation-controlled, alpha-chiral ketone reduction protocol is presented based on titanium tetrachloride and a wide variety of reducing agents. Features of the proposed intermediate titanium chelates necessary to obtain high diastereoselectivity are discussed.
• DERBALI, Y., J. SOC. CHIM. TUNIS, 2,(1988) N 7, C. 9-16
  作者：DERBALI, Y.

  DOI：——

  日期：——
• Novel diastereo- and enantioselectivities in the chiral oxazaborolidinone-promoted asymmetric aldol reaction of highly hindered aldehydes having a quaternary carbon at α position and limitations observed on catalyst (promoter) control
  作者：Syun-ichi Kiyooka、Hirofumi Maeda、Mostofa Abu Hena、Mai Uchida、Chul-Sa Kim、Michio Horiike

  DOI：10.1016/s0040-4039(98)01808-5

  日期：1998.11

  The chiral oxazaborolidinone (1 and 2) -promoted asymmetric aldol reaction of pivalaldehyde with silyl nucleophile 3 resulted in excellent syn selectivity of the corresponding aldol with 96% ee. The catalyst (promoter) control was examined in the reaction with highly hindered aldehydes, 4 and 9. The reaction of 4 in the presence of 2 gave almost enantiopure aldol 7 (>50 : 1) with syn selectivity (4 : 1) in good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions
  作者：Syun-ichi Kiyooka、Mostofa A. Hena

  DOI：10.1021/jo990342r

  日期：1999.7.1

  A shortening of the reaction path can be realized by using a series of the chiral oxazaborolidinone-promoted aldol reaction with respect to the practical synthesis of the (+)-acutiphycin seco acid derivative 5. The linear strategy is based on the utilization of five aldol reactions with a sequence of silyl nucleophiles, 7, 8, 35, 10, and 11, in the presence of stoichiometric amounts of the promoter, 1 or 2. The construction of the relative configuration between the stereogenic centers is diastereoselectively controlled by the stereochemistry of the promoter used in the enantioselective aldol reaction, which is nearly independent of that of the substrate (promoter control).