(5S) methyl 5-hydroxy-5-phenylpentanoate | 156459-87-9

• 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: (5S) methyl 5-hydroxy-5-phenylpentanoate
• 英文别名: (S)-methyl 5-hydroxy-5-phenylpentanoate；methyl (5S)-5-hydroxy-5-phenylpentanoate
• CAS: 156459-87-9
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: HOGIOKMCGZJACN-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S) methyl 5-hydroxy-5-phenylpentanoate 在 双(乙腈)氯化钯(II) 、 正丁基锂 、 camphor-10-sulfonic acid 、 三丁基氯化锡 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 calcium chloride 、 copper dichloride 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 35.0h， 生成 (2'S,2''S,6'S,6''S) 2-O,5-O-dibenzoyl-1-O,6-O-(6,6'-diphenyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-D-myo-inositol
  参考文献：
  名称：

  Dispiroketals in synthesis (part 19)1: Dispiroketals as enantioselective and regioselective protective agents for symmetric cyclic and acyclic polyols.

  摘要：

  The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated. Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.

  DOI：

  10.1016/0957-4166(95)00318-j
• 作为产物：
  描述：

  4-苯甲酰基丁酸甲酯 在 dimethyl sulfide borane 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 甲苯 为溶剂， 以95%的产率得到
  参考文献：
  名称：

  Inhibiting prolyl isomerase activity by hybrid organic–inorganic molecules containing rhodium(II) fragments

  摘要：

  A small molecule containing a rhodium(II) tetracarboxylate fragment is shown to be a potent inhibitor of the prolyl isomerase FKBP12. The use of small molecules conjugates of rhodium(II) is presented as a general strategy for developing new protein inhibitors based on distinct structural and sequence features of the enzyme active site. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.068

文献信息

• Efficient Stereoselective Synthesis of Structurally Diverse γ‐ and δ‐Lactones Using an Engineered Carbonyl Reductase
  作者：Meng Chen、Xiao‐Yan Zhang、Chen‐Guang Xing、Chao Zhang、Yu‐Cong Zheng、Jiang Pan、Jian‐He Xu、Yun‐Peng Bai

  DOI：10.1002/cctc.201900382

  日期：2019.6.6

  efficiently synthesized stereoselectively using an engineered carbonyl reductase from Serratia marcescens (SmCRV4). SmCRV4 exhibited improved activity (up to 500‐fold) and thermostability toward 14 γ‐/δ‐keto acids and esters, compared with the wild‐type enzyme, with 110‐fold enhancement in catalytic efficiency (kcat/Km) toward methyl 4‐oxodecanoate. The preparative synthesis of alkyl and aromatic γ‐ and δ‐lactones

  结构结构多样的γ-和δ-内酯是利用粘质沙雷氏菌（Sm CR V4）中的一种工程化羰基还原酶有效地立体选择性合成的。与野生型酶相比，Sm CR V4表现出更高的活性（最高达500倍）和对14种γ-/δ-酮酸和酯的热稳定性，催化效率提高了110倍（k cat / K m）对4-氧代十二烷甲酸甲酯。证明了烷基和芳香族γ-和δ-内酯的制备合成，其ee率为95％-> 99％，收率为78％-90％。最高时空产量为1175 g L -1  d -1，达到了（R）-γ-癸内酯
• Dispiroketals in synthesis (part 19)1: Dispiroketals as enantioselective and regioselective protective agents for symmetric cyclic and acyclic polyols.
  作者：Robert Downham、Paul J Edwards、David A Entwistle、Andrew B Hughes、Kun Soo Kim、Steven V Ley

  DOI：10.1016/0957-4166(95)00318-j

  日期：1995.10

  The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated. Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.
• Inhibiting prolyl isomerase activity by hybrid organic–inorganic molecules containing rhodium(II) fragments
  作者：Jane M. Coughlin、Rituparna Kundu、Julian C. Cooper、Zachary T. Ball

  DOI：10.1016/j.bmcl.2014.09.068

  日期：2014.11

  A small molecule containing a rhodium(II) tetracarboxylate fragment is shown to be a potent inhibitor of the prolyl isomerase FKBP12. The use of small molecules conjugates of rhodium(II) is presented as a general strategy for developing new protein inhibitors based on distinct structural and sequence features of the enzyme active site. (C) 2014 Elsevier Ltd. All rights reserved.