乙硫酸,[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-,S-苯基酯 | 144192-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 中文名称: 乙硫酸,[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-,S-苯基酯
• 英文名称: (tert-Butyl-dimethyl-silanyloxy)-thioacetic acid S-phenyl ester
• 英文别名: S-phenyl 2-[tert-butyl(dimethyl)silyl]oxyethanethioate
• CAS: 144192-69-8
• 化学式: C₁₄H₂₂O₂SSi
• 分子量: 282.479
• InChiKey: NYWIUDJLAGXPDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙硫酸,[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-,S-苯基酯 在 copper diacetate 、 四氯化钛 、 三乙胺 作用下， 反应 4.5h， 生成 (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Diastereoselective synthesis of anti and syn .alpha.,.beta.-dihydroxy thioesters by titanium enolate aldol condensation

  摘要：

  DOI：

  10.1021/jo00049a053
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 三甲基铝 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 乙硫酸,[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-,S-苯基酯
  参考文献：
  名称：

  α-杂取代硫代乙酸酯与醛和甲硅烷基亚胺的高度对映体和非对映体选择性硼醇醛缩合反应

  摘要：

  衍生自α-杂取代硫代乙酸酯的硼烯酸酯和带有薄荷酮的手性配体与醛反应生成具有出色的非对映异构和对映异构控制的抗羟醛。衍生自α-卤代硫代乙酸叔丁酯并带有薄荷酮的手性配体的硼烯醇盐与亚胺反应，具有优异的非对映和对映体控制能力，可生成合成α-卤代-β-氨基硫酯，可通过在闭环过程中进行简单的闭环反应将其转化为相应的氮丙啶减少LAH。合成了抗菌素（+）-噻吩酚和（-）-氟苯尼考的​​关键前体。

  DOI：

  10.1016/s0040-4020(97)00251-2

文献信息

• 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：——
• A highly enantio- and diastereoselective aldol reaction for α-heterosubstituted thioacetates
  作者：Cesare Gennari、Anna Vulpetti、Daniela Moresca

  DOI：10.1016/s0040-4039(00)76987-5

  日期：1994.7

  Boron enolates derived from alpha-heterosubstituted thioacetates and bearing menthone-derived chiral ligands react with aldehydes to give anti aldols with excellent diastero- and enantiocontrol.
• 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, Moresca Daniela, Tetrahedron Lett, 35 (1994) N 27, S 4857-4860
  作者：Gennari Cesare, Vulpetti Anna, Moresca Daniela

  DOI：——

  日期：——