(S)-3-(benzyloxy)butanoic acid methyl ester | 90124-15-5

• 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)butanoic acid methyl ester
• 英文别名: methyl (S)-3-(benzyloxy)butanoate；methyl (S)-3-benzyloxybutyrate；methyl (3S)-3-phenylmethoxybutanoate
• CAS: 90124-15-5
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: JXBBMSDQNOELFF-JTQLQIEISA-N

物化性质

• 沸点：
  294.5±15.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-(benzyloxy)butanoic acid methyl ester 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 生成 (3S)-3-(苄氧基)丁酸
  参考文献：
  名称：

  Enantiomerically-enhanced nutritional energy substrates

  摘要：

  合成对映酯被用作肠内或静脉营养配方的能量底物。这些底物以几乎单异构体或单环异构体的形式提供，可以被患者新陈代谢轻松利用。

  公开号：

  US06306828B1
• 作为产物：
  描述：

  (S)-3-羟基丁酸甲酯 、 2,2,2-三氯乙酰胺苄酯 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到(S)-3-(benzyloxy)butanoic acid methyl ester
  参考文献：
  名称：

  胆固醇药物二羟基二丁醚的立体异构体的首次合成与表征

  摘要：

  二羟基二丁醚（DHBE）是一种用于治疗胆结石和肝脏疾病的霍乱药物，由于其具有霍乱活性和保肝作用。该药物是三种区域异构体的混合物。主要的区域异构体3-（3-羟基丁氧基）-1-丁醇（III）包含四种立体异构体，包括（R）-3-（（（R）-3-羟基丁氧基）-1-丁醇（IIIa），（R）-3 -（（S）-3-羟基丁氧基）-1-丁醇（IIIb），（S）-3-（（R）-3-羟基丁氧基）-1-丁醇（IIIc）和（S）-3-（（S）-3-羟基丁氧基）-1-丁醇（IIId）。本文首次首次合成了四种立体异构体。

  DOI：

  10.1002/cjoc.201500450

文献信息

• Enantiomerically-enhanced nutritional energy substrates
  申请人：Baxter International, Inc.

  公开号：US06306828B1

  公开（公告）日：2001-10-23

  Synthetic enantiomeric esters are employed as energy substrates for parenteral or enteral nutritional formulations. The substrates are provided in substantially monoisomeric or anomeric forms readily utilized in patient metabolism.

  合成对映酯被用作肠内或静脉营养配方的能量底物。这些底物以几乎单异构体或单环异构体的形式提供，可以被患者新陈代谢轻松利用。
• Sasaki, Makoto; Matsumori, Nobuaki; Maruyama, Takahiro, Angewandte Chemie, 1996, vol. 108, # 15, p. 1782 - 1785
  作者：Sasaki, Makoto、Matsumori, Nobuaki、Maruyama, Takahiro、Nonomura, Taro、Murata, Michio、et al.

  DOI：——

  日期：——
• Synthesis of N-Butyl Side Chain Hydroxylated Metabolites of Roxifiban, a Platelet Glycoprotein IIb/IIIa Receptor Antagonist
  作者：Jung-Hui Sun、George C. Emmett、Janice L. Hytrek、Jia-Sheng Yan、A. Christine Tabaka-Blom、Christopher A. Teleha

  DOI：10.3987/com-04-10087

  日期：——

  Syntheses of three n-butyl side chain hydroxylated metabolites of Roxifiban (5, 6a and 6b) are reported. Initial use of benzyl as hydroxyl protecting group gave poor yield during its removal by catalytic hydrogenation, due to complication from N-O cleavage of the isoxazoline. This problem was eliminated by the use of TBDMS as the hydroxyl protecting group. The chemical structures of these metabolites as well as the intermediates have been fully characterized.
• Synthesis and Structure of Linear and Cyclic Oligomers of 3-Hydroxybutanoic Acid with Specific Sequences of (R)- and (S)-Configurations
  作者：Beat M. Bachmann、Dieter Seebach

  DOI：10.1002/(sici)1522-2675(19981216)81:12<2430::aid-hlca2430>3.0.co;2-w

  日期：1998.12.16

  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.
• First Synthesis and Characterization of Stereoisomers of Choleretic Drug Dihydroxydibutylether
  作者：Qiming Yue、Yi Zhao、Baohou Sun、Li Hai、Li Guo、Yong Wu

  DOI：10.1002/cjoc.201500450

  日期：2015.10

  Dihydroxydibutylether (DHBE) is a choleretic drug used for the treatment of gallstone and hepatic disorders due to its choleretic activity and hepatoprotective action. The drug is a mixture of three regioisomers. The main regioisomer 3‐(3‐hydroxylbutoxy)‐1‐butanol (III) contains four stereoisomers, including (R)‐3‐((R)‐3‐hydroxylbutoxy)‐1‐butanol (IIIa), (R)‐3‐((S)‐3‐hydroxylbutoxy)‐1‐butanol (IIIb)

  二羟基二丁醚（DHBE）是一种用于治疗胆结石和肝脏疾病的霍乱药物，由于其具有霍乱活性和保肝作用。该药物是三种区域异构体的混合物。主要的区域异构体3-（3-羟基丁氧基）-1-丁醇（III）包含四种立体异构体，包括（R）-3-（（（R）-3-羟基丁氧基）-1-丁醇（IIIa），（R）-3 -（（S）-3-羟基丁氧基）-1-丁醇（IIIb），（S）-3-（（R）-3-羟基丁氧基）-1-丁醇（IIIc）和（S）-3-（（S）-3-羟基丁氧基）-1-丁醇（IIId）。本文首次首次合成了四种立体异构体。