tert-butyl (3R)-3-(<(3'R)-3'-(<(3''R)-3''-(benzyloxy)butanoyl>oxy)butanoyl>oxy)butanoate | 116761-29-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (3R)-3-(<(3'R)-3'-(<(3''R)-3''-(benzyloxy)butanoyl>oxy)butanoyl>oxy)butanoate
• 英文别名: (3R)-3-<<(3'R)-3'-<<(3''R)-3''-(benzyloxy)butanoyl>oxy>butanoyl>oxy>butanoic acid tert-butyl ester；[(2R)-4-[(2R)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutan-2-yl]oxy-4-oxobutan-2-yl] (3R)-3-phenylmethoxybutanoate
• CAS: 116761-29-6
• 化学式: C₂₃H₃₄O₇
• 分子量: 422.519
• InChiKey: OKDWGVVRICOWRR-KZNAEPCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (3R)-3-(<(3'R)-3'-(<(3''R)-3''-(benzyloxy)butanoyl>oxy)butanoyl>oxy)butanoate 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 (3R)-3-<<(3'R)-3'-<<(3''R)-3''-hydroxybutanoyl>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：

  2,2,2-三氯乙酰胺苄酯 在 氢氧化钾 、 氯化亚砜 、 三氟甲磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 环己烷 、 水 为溶剂， 反应 6.0h， 生成 tert-butyl (3R)-3-(<(3'R)-3'-(<(3''R)-3''-(benzyloxy)butanoyl>oxy)butanoyl>oxy)butanoate
  参考文献：
  名称：

  在山口的大环内酯化条件下，分别由（R）-或（S）-3-羟基丁酸高产合成20-，24-和28-元大环戊内酯，-己内酯和-庚内酯†

  摘要：

  大环戊内酯1，己内酯2和庚内酯3构成ca。形成在所述低聚物的80％约 在山口的大环内酯化条件下，对映体纯的3-羟基丁酸的收率为50％。报道了M H +，M Na +和M Cs +的FAB质谱图（图2、3、5和6）。未检测到环状四聚体。环状低聚物，单体和聚合物（PHB）的1 H-NMR谱图非常相似（图4）。3-羟基丁酸的开链二聚体和四聚体的直接合成和尝试的环化作用不会导致环状四聚体的分离。

  DOI：

  10.1002/hlca.19880710119

文献信息

• SEEBACH, DIETER;BRANDLI, URS;SCHNURRENBERGER, PETER;PRZYBYLSKI, MICHAEL, HELV. CHIM. ACTA, 71,(1988) N 1, 155-167
  作者：SEEBACH, DIETER、BRANDLI, URS、SCHNURRENBERGER, PETER、PRZYBYLSKI, MICHAEL

  DOI：——

  日期：——