[(2R,4R)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-6-oxo-tetrahydro-pyran-4-yl]-thioacetic acid S-ethyl ester | 149083-11-4

• 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: [(2R,4R)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-6-oxo-tetrahydro-pyran-4-yl]-thioacetic acid S-ethyl ester
• CAS: 149083-11-4
• 化学式: C₁₉H₂₆O₄S
• 分子量: 350.479
• InChiKey: ZQGAJNNIUQCOCP-DJIMGWMZSA-N

物化性质

• 沸点：
  495.6±15.0 °C(predicted)
• 密度：
  1.125±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(2R,4R)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-6-oxo-tetrahydro-pyran-4-yl]-thioacetic acid S-ethyl ester 在 二异丁基氢化铝 作用下， 生成 [(R)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-6-hydroxy-tetrahydro-pyran-4-yl]-acetaldehyde
  参考文献：
  名称：

  Synthetic studies on the rhizoxins. 1. Two stereoselective routes to a functionalized C(1)-C(9) subunit

  摘要：

  Two syntheses of a potential C1-C-9 subunit of rhizoxin are described. In the first, chelation-controlled allylstannane addition to optically pure aldehyde 3, conversion to unsaturated ester 7, and stereoselective intramolecular Michael addition is used to establish the relative stereochemistry at C-7 and C-8 (rhizoxin numbering). In the second, an Evans aldol condensation is used to control absolute and relative stereochemistry at these centers. Both approaches use thermodynamic control to establish the correct stereochemistry at C5.

  DOI：

  10.1021/jo00067a003
• 作为产物：
  描述：

  (3R,4S,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-4-ethylsulfanylcarbonylmethyl-2-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester 在 水 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 以86%的产率得到[(2R,4R)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-6-oxo-tetrahydro-pyran-4-yl]-thioacetic acid S-ethyl ester
  参考文献：
  名称：

  Synthetic studies on the rhizoxins. 1. Two stereoselective routes to a functionalized C(1)-C(9) subunit

  摘要：

  Two syntheses of a potential C1-C-9 subunit of rhizoxin are described. In the first, chelation-controlled allylstannane addition to optically pure aldehyde 3, conversion to unsaturated ester 7, and stereoselective intramolecular Michael addition is used to establish the relative stereochemistry at C-7 and C-8 (rhizoxin numbering). In the second, an Evans aldol condensation is used to control absolute and relative stereochemistry at these centers. Both approaches use thermodynamic control to establish the correct stereochemistry at C5.

  DOI：

  10.1021/jo00067a003