(3R)-3-<<(3'S)-3'-hydroxybutanoyl>oxy>butanoic acid tert-butyl ester | 220095-32-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (3R)-3-<<(3'S)-3'-hydroxybutanoyl>oxy>butanoic acid tert-butyl ester
• 英文别名: [(2R)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutan-2-yl] (3S)-3-hydroxybutanoate
• CAS: 220095-32-9
• 化学式: C₁₂H₂₂O₅
• 分子量: 246.304
• InChiKey: QLXTYEAOSUPHQK-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R)-3-<<(3'S)-3'-hydroxybutanoyl>oxy>butanoic acid tert-butyl ester 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 (S,S,S,R,R,R,R,R)-α-benzyl-ω-(tert-butoxy)octakis
  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：

  (R)-3-(benzyloxy)butanoic acid tert-butyl ester 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 生成 (3R)-3-<<(3'S)-3'-hydroxybutanoyl>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