(+/-)-3-hydroxy-4-phenylsulfanylbutyric acid ethyl ester | 766546-98-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (+/-)-3-hydroxy-4-phenylsulfanylbutyric acid ethyl ester
• 英文别名: Ethyl 3-hydroxy-4-phenylsulfanylbutanoate；ethyl 3-hydroxy-4-phenylsulfanylbutanoate
• CAS: 766546-98-9
• 化学式: C₁₂H₁₆O₃S
• 分子量: 240.323
• InChiKey: CVBHJSQPYNCWPC-UHFFFAOYSA-N

物化性质

• 沸点：
  388.8±32.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-3-hydroxy-4-phenylsulfanylbutyric acid ethyl ester 在 PBS buffer 、 碘 、 三甲基铝 、 magnesium 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 (S)-2-hydroxy-1-phenylsulfanylheptan-4-one
  参考文献：
  名称：

  对映体富集的硫烷基羟醛产品的生物催化途径

  摘要：

  衍生自含硫或硒的受体的醛醇缩合产物是在抗体84G3存在下，通过对映体过量范围为56％至70％的动力学拆分制备的。对于衍生自具有三个不同受体的硫代甲氧基丙酮的硫烷基醛醇缩醛产物，其对映选择性的水平更高（对映体过量均超过96％）。

  DOI：

  10.1016/j.tet.2004.06.033
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (+/-)-3-hydroxy-4-phenylsulfanylbutyric acid ethyl ester
  参考文献：
  名称：

  Total Synthesis of Leustroducsin B

  摘要：

  A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).

  DOI：

  10.1021/ja0340679

文献信息

• A biocatalytic route to enantioenriched, sulfanyl aldol products
  作者：C. Baker-Glenn、R. Ancliff、V. Gouverneur

  DOI：10.1016/j.tet.2004.06.033

  日期：2004.8

  The aldol products derived from sulfur- or selenium containing acceptors were prepared by kinetic resolution in the presence of antibody 84G3 with enantiomeric excesses ranging from 56 to 70%. Much higher level of enantioselectivity was obtained (enantiomeric excesses all superior to 96%) for sulfanyl aldol products derived from thiomethoxyacetone with three different acceptors.

  衍生自含硫或硒的受体的醛醇缩合产物是在抗体84G3存在下，通过对映体过量范围为56％至70％的动力学拆分制备的。对于衍生自具有三个不同受体的硫代甲氧基丙酮的硫烷基醛醇缩醛产物，其对映选择性的水平更高（对映体过量均超过96％）。
• Total Synthesis of Leustroducsin B
  作者：Kousei Shimada、Yosuke Kaburagi、Tohru Fukuyama

  DOI：10.1021/ja0340679

  日期：2003.4.1

  A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).