(20R)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate | 161579-69-7

• 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)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate
• CAS: 161579-69-7
• 化学式: C₂₈H₃₇BrO₄
• 分子量: 517.503
• InChiKey: KHEWTMKFRAEWMS-LGTGLOTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (20R)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate 在 盐酸 、 sodium hydroxide 、 jones reagent 、 对甲苯磺酸 、 锌 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醚 、 氯仿 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 72.49h， 生成 (19E)-3β,17-dihydroxy-20-oxopregn-5-en-19-al 19-(O-carboxymethyl)oxime
  参考文献：
  名称：

  Synthesis of (19E)-3β,17-dihydroxy-20-oxopregn-5-en-19-al 19-(O-carboxymethyl)oxime, new steroidal hapten for 17-hydroxypregnenolone

  摘要：

  A synthesis of (19E)-3 beta,17-dihydroxy-20-oxopregn-5-en-19-al 19-(O-carboxymethyl)oxime (15), is reported Hydride reduction of ketone 1 gave the (20R)-hydroxy derivative 2 as the main product. Formylation of 2 followed by cleavage of the epoxide ring and mild Jones oxidation afforded aldehyde 6. Oximation with (O-carboxymethyl)hydroxylamine and subsequent methylation yielded methyl ester 8 which was selectively hydrolyzed to alcohol 9 and oxidized to ketone 10. Enolacetylation, epoxidation, and hydrolysis led to the desired 19-(O-carboxymethyl) oxime derivative of 17-hydroxypregnenolone 15.

  DOI：

  10.1016/0039-128x(94)90101-5
• 作为产物：
  描述：

  3β-benzoyloxy-5-bromo-6β,19-epoxy-5α-pregnan-20-one 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以74%的产率得到(20R)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate
  参考文献：
  名称：

  Synthesis of (19E)-3β,17-dihydroxy-20-oxopregn-5-en-19-al 19-(O-carboxymethyl)oxime, new steroidal hapten for 17-hydroxypregnenolone

  摘要：

  A synthesis of (19E)-3 beta,17-dihydroxy-20-oxopregn-5-en-19-al 19-(O-carboxymethyl)oxime (15), is reported Hydride reduction of ketone 1 gave the (20R)-hydroxy derivative 2 as the main product. Formylation of 2 followed by cleavage of the epoxide ring and mild Jones oxidation afforded aldehyde 6. Oximation with (O-carboxymethyl)hydroxylamine and subsequent methylation yielded methyl ester 8 which was selectively hydrolyzed to alcohol 9 and oxidized to ketone 10. Enolacetylation, epoxidation, and hydrolysis led to the desired 19-(O-carboxymethyl) oxime derivative of 17-hydroxypregnenolone 15.

  DOI：

  10.1016/0039-128x(94)90101-5