S-tert-butyl 2-hydroxyethanethioate | 186596-31-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: S-tert-butyl 2-hydroxyethanethioate
• CAS: 186596-31-6
• 化学式: C₆H₁₂O₂S
• 分子量: 148.226
• InChiKey: PQQRYQJBJQABAY-UHFFFAOYSA-N

物化性质

• 沸点：
  205.3±23.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-tert-butyl 2-hydroxyethanethioate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S)-3-Benzoylamino-2-hydroxy-3-phenyl-thiopropionic acid S-tert-butyl ester
  参考文献：
  名称：

  Gennari, Cesare; Vulpetti, Anna; Donghi, Monica, Angewandte Chemie, 1996, vol. 108, # 15, p. 1809 - 1812

  摘要：

  DOI：
• 作为产物：
  描述：

  羟乙酸甲酯 、 叔丁基硫醇 在 三甲基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以53%的产率得到S-tert-butyl 2-hydroxyethanethioate
  参考文献：
  名称：

  Gennari, Cesare; Vulpetti, Anna; Donghi, Monica, Angewandte Chemie, 1996, vol. 108, # 15, p. 1809 - 1812

  摘要：

  DOI：

文献信息

• Taxol Semisynthesis:  A Highly Enantio- and Diastereoselective Synthesis of the Side Chain and a New Method for Ester Formation at C-13 Using Thioesters
  作者：Cesare Gennari、Michela Carcano、Monica Donghi、Nicola Mongelli、Ermes Vanotti、Anna Vulpetti

  DOI：10.1021/jo9703212

  日期：1997.7.1

  A very simple, new, and straightforward approach to the Paclitaxel (Taxol) and Docetaxel (Taxotere) side chains has been developed using the imine addition reaction of thioester-derived boron enolates bearing chiral ligands. The addition reaction was studied extensively, using a combination of different thioesters (ROCH2COSPh, ROCH(2)60St-Bu), oxygen protecting groups (R = Bn, TBDMS, COPh, EE, TMS), chiral boron ligands [derived from both (-) and (+)-menthone], imines (PhCH=NSiMe3, PhCH=NCOPh), and in the presence or in the absence of additional Lewis acids (BF3-OEt2, Et2AlCl, TiCl4). The side chain was assembled in a few steps with the correct relative (syn) and absolute stereochemistry (2R,3S). The stereochemical outcome of the boron-mediated reaction was rationalized using chair vs boat transition state structures. A new direct route for attachment of the side chains to the baccatin nucleus using thioester chemistry has also been developed. By treatment of a mixture of a thioester (8, 12, or 17) and protected baccatin III (2b, 2c) with LHMDS, the 13-O acylated compounds were obtained in high yield (up to 90%). Hydrolysis of 18b gave Paclitaxel (1a) in 80% yield.
• Gennari, Cesare; Vulpetti, Anna; Donghi, Monica, Angewandte Chemie, 1996, vol. 108, # 15, p. 1809 - 1812
  作者：Gennari, Cesare、Vulpetti, Anna、Donghi, Monica、Mongelli, Nicola、Vanotti, Ermes

  DOI：——

  日期：——