(2S,3S)-2,4,4-trimethyl-1,3-pentanediol | 105497-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S)-2,4,4-trimethyl-1,3-pentanediol
• 英文别名: (2S,3S)-2,4,4-trimethylpentane-1,3-diol
• CAS: 105497-75-4
• 化学式: C₈H₁₈O₂
• 分子量: 146.23
• InChiKey: LDKQSAYLQSMHQP-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,4,4-trimethyl-1,3-pentanediol 、 2,2-二甲氧基丙烷 在 camphor-10-sulfonic acid 作用下， 以 丙酮 为溶剂， 反应 0.33h， 以98%的产率得到(2S,3S)-1,3-O-isopropylidene-2,4,4-trimethylpentane-1,3-diol
  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
• 作为产物：
  描述：

  [(1R,2S)-2-[methyl(1,2,3,4,5,6,7,8-octahydroanthracen-9-ylsulfonyl)amino]-1-phenylpropyl] (2R,3S)-3-hydroxy-2,4,4-trimethylpentanoate 在 二异丁基氢化铝 作用下， 生成 (2S,3S)-2,4,4-trimethyl-1,3-pentanediol
  参考文献：
  名称：

  的程度顺式-选择性为羧酸酯的硼介导的不对称醛醇缩合反应

  摘要：

  为顺式选择性羟醛缩合反应的新的手性试剂已经被开发了基于最近的发现，即羧酸酯的硼介导的醛醇缩合反应的立体化学通过该酯的醇部分的膨松度的控制，通过适当选择试剂，并受烯醇化条件的影响。这种易于获得的廉价试剂已被用于大环内酯单萜内酯的合成研究中。

  DOI：

  10.1016/s0040-4039(98)00123-3

文献信息

• Asymmetric synthesis using diisopropyl tartrate modified (E)- and (Z)-crotylboronates: preparation of the chiral crotylboronates and reactions with achiral aldehydes
  作者：William R. Roush、Kaori Ando、Daniel B. Powers、Alan D. Palkowitz、Ronald L. Halterman

  DOI：10.1021/ja00173a023

  日期：1990.8

  Crotylboronates undergo highly diastereo- and enantioselective reactions with aliphatic (linear or α-monobranched; 72-91% ee), aromatic and α,β-unsaturated aldehydes (55-74% ee). The reaction diastereoselectivity closely parallels the reagent isomeric purity especially for reactions performed at −78 o C. The enantioselectivity is best in toluene for all substrates except benzaldehyde where best results

  巴豆基硼酸酯与脂肪族（线性或 α-单支链；72-91% ee）、芳香族和 α,β-不饱和醛（55-74% ee）发生高度非对映选择性和对映选择性反应。反应的非对映选择性与试剂异构体纯度密切相关，特别是对于在 -78 o C 下进行的反应。对所有底物的对映选择性在甲苯中最佳，但苯甲醛除外，因为苯甲醛在 THF 中获得最佳结果。本研究中合成的 14 种高烯丙醇中有 9 种的相对和绝对立体化学是通过与 Sharpless 不对称环氧化制备的环氧醇的相关性来确定的
• Sacha, Hubert; Waldmueller, Delia; Braun, Manfred, Chemische Berichte, 1994, vol. 127, # 10, p. 1959 - 1968
  作者：Sacha, Hubert、Waldmueller, Delia、Braun, Manfred

  DOI：——

  日期：——
• Braun, Manfred; Sacha, Hubert, Angewandte Chemie, 1991, vol. 103, # 10, p. 1369 - 1371
  作者：Braun, Manfred、Sacha, Hubert

  DOI：——

  日期：——
• Organoboron compounds in organic synthesis. 4. Asymmetric aldol reactions
  作者：Satoru. Masamune、Tsuneo. Sato、ByeongMoon. Kim、Theodor A. Wollmann

  DOI：10.1021/ja00286a036

  日期：1986.12
• 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).