S-ethyl (2R,3R)-4-(benzyloxy)-3-hydroxy-2-methylbutanethioate | 221082-64-0

• 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-ethyl (2R,3R)-4-(benzyloxy)-3-hydroxy-2-methylbutanethioate
• 英文别名: S-ethyl (2R,3R)-3-hydroxy-2-methyl-4-phenylmethoxybutanethioate
• CAS: 221082-64-0
• 化学式: C₁₄H₂₀O₃S
• 分子量: 268.377
• InChiKey: XRIOLWFMUWGORN-YPMHNXCESA-N

物化性质

• 沸点：
  406.2±40.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  S-ethyl (2R,3R)-4-(benzyloxy)-3-hydroxy-2-methylbutanethioate 在 palladium on activated charcoal 三甲基硅烷 、 Proton-Sponge 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 20.17h， 生成 (2R,3R)-3-methoxy-2-methyl-4-phenylmethoxybutanal
  参考文献：
  名称：

  Total Synthesis of (+)-Cystothiazole A

  摘要：

  The total synthesis of cystothiazole A is described. Key steps of the synthesis include an Evans asymmetric catalytic aldol reaction, which established the required C-4-C-5 stereochemistry. The [2,4']-bis(thiazole) was obtained applying our methodology of electrophilic activation of amide. Semistabilized Wittig reaction between the phosphonium salt 3 and the aldehyde 2 afforded 1 in nine linear steps and 38% overall yield.

  DOI：

  10.1021/ol035600s
• 作为产物：
  描述：

  [1-(ethylthio)prop-1-enyloxy]trimethylsilane 、 苄氧基乙醛 在 [Cu((R,R)-phenyl-bis(oxazolinyl)pyridine)](SbF₆)2 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 S-ethyl 4-(benzyloxy)-3-hydroxy-2-methylbutanethioate 、 S-ethyl 4-(benzyloxy)-3-hydroxy-2-methylbutanethioate 、 S-ethyl (2R,3R)-4-(benzyloxy)-3-hydroxy-2-methylbutanethioate
  参考文献：
  名称：

  Total Synthesis of (+)-Cystothiazole A

  摘要：

  The total synthesis of cystothiazole A is described. Key steps of the synthesis include an Evans asymmetric catalytic aldol reaction, which established the required C-4-C-5 stereochemistry. The [2,4']-bis(thiazole) was obtained applying our methodology of electrophilic activation of amide. Semistabilized Wittig reaction between the phosphonium salt 3 and the aldehyde 2 afforded 1 in nine linear steps and 38% overall yield.

  DOI：

  10.1021/ol035600s

文献信息

• Total Synthesis of (+)-Cystothiazole A
  作者：Patrick L. DeRoy、André B. Charette

  DOI：10.1021/ol035600s

  日期：2003.10.1

  The total synthesis of cystothiazole A is described. Key steps of the synthesis include an Evans asymmetric catalytic aldol reaction, which established the required C-4-C-5 stereochemistry. The [2,4']-bis(thiazole) was obtained applying our methodology of electrophilic activation of amide. Semistabilized Wittig reaction between the phosphonium salt 3 and the aldehyde 2 afforded 1 in nine linear steps and 38% overall yield.