17β-tert-butoxy-19-(3,5-dimethyl-isoxazol-4-yl)-5-oxo-des-A-androst-9-ene-6ξ-carboxylic acid methyl ester | 53655-70-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 17β-tert-butoxy-19-(3,5-dimethyl-isoxazol-4-yl)-5-oxo-des-A-androst-9-ene-6ξ-carboxylic acid methyl ester
• CAS: 53655-70-2；53655-71-3
• 化学式: C₂₆H₃₇NO₅
• 分子量: 443.583
• InChiKey: WDHVGCOGRVMQOY-PNEZFWMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  78.63
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-氯甲基-3,5-二甲基异噁唑 生成 17β-tert-butoxy-19-(3,5-dimethyl-isoxazol-4-yl)-5-oxo-des-A-androst-9-ene-6ξ-carboxylic acid methyl ester
  参考文献：
  名称：

  甾族合成中间体BCD-三环9-en-5-ones的C（10）-甲基化。

  摘要：

  AbstractA literature survey indicated that stereospecific non‐reductive β‐face methylation at C(10) of steroidal synthesis intermediate BCD‐tricyclic 9‐en‐5‐ones had never been effected. An attempt to define the factors controlling the β/α product ratio in such alkylations was made. The course of methylation is significantly affected by the temperature. In the best case, methylation of the sodium enolate of 17 β‐t‐butoxy‐19‐(3,5‐dimethyl‐4‐isoxazolyl)‐deA‐androst‐9‐en‐5‐one (18) in tetrahydrofuran at − 78° gave a β/α product ratio of > 5:1. The reaction mixture contained no unalkylated or dialkylated materials, indicating that enolate exchange probably did not occur at this temperature. The 10β‐methylated product 23, isolated in 78% yield, was converted to Δ9(ll)‐dehydrotestosterone (29). Compounds 23 and 29 are potential intermediates for the synthesis of 11‐oxygenated steroids.

  DOI：

  10.1002/hlca.19740570433