(20R)-ethyl 3β-(tert-butyldimethylsiloxy)-20-deuteriopregn-5-en-21-oate | 135215-55-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (20R)-ethyl 3β-(tert-butyldimethylsiloxy)-20-deuteriopregn-5-en-21-oate
• 英文别名: ethyl (2R)-2-[(3S,8S,9S,10R,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-deuterioacetate
• CAS: 135215-55-3
• 化学式: C₂₉H₅₀O₃Si
• 分子量: 475.792
• InChiKey: WMMMKNBURAYMSU-RQCPHALLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.91
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-pregn-5-en-21-oic acid,ethyl ester 在 偶氮二异丁腈 、 triphenylstannane-d₁ 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (20R)-ethyl 3β-(tert-butyldimethylsiloxy)-20-deuteriopregn-5-en-21-oate
  参考文献：
  名称：

  Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates

  摘要：

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.

  DOI：

  10.1021/jo00042a029

文献信息

• Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates
  作者：David J. Hart、Ramanarayanan Krishnamurthy

  DOI：10.1021/jo00042a029

  日期：1992.7

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.