(3S)-3-<<(3'S)-3'-hydroxybutanoyl>oxy>butanoic acid tert-butyl ester | 220095-30-7

• 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: (3S)-3-<<(3'S)-3'-hydroxybutanoyl>oxy>butanoic acid tert-butyl ester
• 英文别名: [(2S)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutan-2-yl] (3S)-3-hydroxybutanoate
• CAS: 220095-30-7
• 化学式: C₁₂H₂₂O₅
• 分子量: 246.304
• InChiKey: QLXTYEAOSUPHQK-IUCAKERBSA-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：

  (3S)-3-<<(3'S)-3'-hydroxybutanoyl>oxy>butanoic acid tert-butyl ester 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (3S)-3-<<(3'S)-3'-<<(3''S)-3''-<<(3'''R)-3'''-(benzyloxy)butanoyl>oxy>butanoyl>oxy>butanoyl>oxy>butanoic acid
  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：

  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'-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

文献信息

• Preparation, Structure, and Properties of All Possible Cyclic Dimers (Diolides) of 3-Hydroxybutanoic Acid
  作者：Dieter Seebach、Torsten Hoffmann、Florian N. M. Kühnle、Joachim N. Kinkel、Michael Schulte

  DOI：10.1002/hlca.19950780611

  日期：1995.9.20

  Accordingly, these compounds show reactivities similar to those of carboxylic-acid anhydrides or even acid chlorides. They cannot be chromatographed on silica gel, and they react with primary, secondary, and tertiary alcohols, and with amines to form derivatives of open chain 3-HB ‘dimers’, hydroxy acids 6, esters 7, and amides 8 (Scheme 2). The rate of acid-catalyzed ring opening of the diolides 1 with

  与所提出的结构连接的反式聚之间由一个复杂的-membRAne细胞离子通道[（[R多磷酸钙）-3-羟基丁酸]（P（3-HB））和，CAPP我（约150个单位每），它应该包含s-顺式键甚至更高的酯构象，我们已经制备并研究了3-HB环二聚体（乙交酯1）的性质。的所有可能的形式1中，外消旋-时，内消旋-和对映体纯（- [R ，- [R ）-和（小号，小号制备，纯化和表征化合物。合成（方案1）从琥珀酸二甲酯开始，关键步骤是外消旋-和内消旋-2,5-二甲基环己烷-1,4-二酮5的Baeyer-Villiger氧化。所述外消旋-diolide 1物用制备型色谱法解决CHIRALCEL OD柱（图1）。通过X射线衍射确定RAc - 1（图3）和meso - 1（图5）的晶体结构：二醇化物1含有顺式-酯键和酯基，其构象位于旋转过渡态的一半（图2）。对于二元醇化物1，建议的应变能高达17.8kcal / mo