(S)-3-(benzyloxy)butanoyl chloride | 182819-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-(benzyloxy)butanoyl chloride
• 英文别名: (S)-3-O-benzylbutyryl chloride；(3S)-3-phenylmethoxybutanoyl chloride
• CAS: 182819-80-3
• 化学式: C₁₁H₁₃ClO₂
• 分子量: 212.676
• InChiKey: VWZKBYOPZMBEJZ-VIFPVBQESA-N

物化性质

• 沸点：
  280.9±23.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-(benzyloxy)butanoyl chloride 在 吡啶 、 草酰氯 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (3R)-3-<<(3'S)-3'-<<(3''S)-3''-<<(3'''S)-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：

  2,2,2-三氯乙酰胺苄酯 在 sodium hydroxide 、 氯化亚砜 、 三氟甲磺酸 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (S)-3-(benzyloxy)butanoyl chloride
  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

文献信息

• Total Syntheses of Conjugation‐Ready Repeating Units of<i>Acinetobacter baumannii</i>AB5075 for Glycoconjugate Vaccine Development
  作者：Shuo Zhang、Peter H. Seeberger

  DOI：10.1002/chem.202103234

  日期：2021.12.9

  the repeating unit of A. baumannii AB5075 as well as two analogues containing a challenging (S)-3-hydroxybutanoyl chain were synthesized. All of the oligosaccharides bear an amino group that allows for the covalent attachment to glycan microarrays and carrier proteins. These densely functionalized aminoglycoside trisaccharides are the basis for the development of novel glycoconjugate vaccines against

  使用高效和立体选择性的糖基化和双序列倒置策略，合成了鲍曼不动杆菌AB5075 的重复单元以及含有具有挑战性的 ( S )-3-羟基丁酰基链的两个类似物。所有寡糖都带有氨基，可以共价连接到聚糖微阵列和载体蛋白上。这些密集功能化的氨基糖苷三糖是开发针对鲍曼不动杆菌的新型糖复合物疫苗的基础。
• REETZ, M. T.;KESSELER, K.;JUNG, A., ANGEW. CHEM., 1985, 97, N 11, 989-990
  作者：REETZ, M. T.、KESSELER, K.、JUNG, A.

  DOI：——

  日期：——