tert-butyl (3S)-3-acetyloxybutanoate | 120444-07-7

• 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: tert-butyl (3S)-3-acetyloxybutanoate
• CAS: 120444-07-7
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: WYAGQRBMQSEZRH-ZETCQYMHSA-N

物化性质

• 沸点：
  190.4±13.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S)-3-acetyloxybutanoate 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 生成 (3S)-3-<<(3'S)-3'-<<(3''S)-3''-<<(3'''R)-3'''-(benzyloxy)butanoyl>oxy>butanoyl>oxy>butanoyl>oxy>butanoic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Structure of Linear and Cyclic Oligomers of 3-Hydroxybutanoic Acid with Specific Sequences of (R)- and (S)-Configurations

  摘要：

  To study the stereoselectivity of enzymatic cleavage of poly(3-hydroxybutyrates) (PHB) in a well-defined system (purified depolymerase and monodisperse substrate of specific relative configuration), linear and cyclic oligomers of HE (OHBs) containing (R)- and (S)-3-hydroxybutanoate residues were synthesized. The starting material (R)-HB was prepared from natural sPHB, and (S)-HB by enantioselective reduction of 3-oxobutanoate: with yeast or with H-2/Noyori-Taber catalyst (Scheme 2). The HE building blocks were then protected (O-benzyl/tert-butyl ester; Scheme 3) and coupled to give dimers 3, 4 tetramers 5-9, and octamers 10-18; for analytical comparison, a 3mer, 5mer, 6mer, and 7mer (19-22) were also prepared. Two of the tetramers were subjected to macrolactonization conditions (Yamaguchi) to give the cyclic tetramers 23 and 25 and octamers 24 and 26. All new compounds were fully characterized (m.p., [alpha](D), CD, IR, H-1- and C-13-NMR, MS, elemental analysis). Single-crystal X-ray structure analyses were performed with oligolides 24 and 25 ( Figs. 2 and 4), and the structures, as well as the crystal packing, were compared with those of analogs containing only (R)-HB units or consisting of 3-amino- instead of 3-hydroxybutanoic-acid moieties.

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2430::aid-hlca2430>3.0.co;2-w
• 作为产物：
  描述：

  3-乙酰氧基丁酸叔丁酯 生成 tert-butyl (3S)-3-acetyloxybutanoate
  参考文献：
  名称：

  （±）-羟基链烷酸酯的生物催化拆分。一种增强脂酶催化的酯水解的对映体特异性的策略。

  摘要：

  已经开发了用于制备各种高光学纯度的多种-和-羟基链烷酸酯的通用生物催化拆分方法。该方法的值得注意的特征在于在羧基末端选择不可水解的酯，以改善在脂肪酶催化的酰氧基酯水解中的对映体特异性。

  DOI：

  10.1016/s0040-4039(00)80643-7

文献信息

• SCILIMATI, A.;NGOOI, T. K.;SIH, CHARLES J., TETRAHEDRON LETT., 29,(1988) N 39, C. 4927-4930
  作者：SCILIMATI, A.、NGOOI, T. K.、SIH, CHARLES J.

  DOI：——

  日期：——