(20R)-19-hydroxypregn-5-ene-3β,20-diyl 3-benzoate 20-formate | 161579-72-2

• 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)-19-hydroxypregn-5-ene-3β,20-diyl 3-benzoate 20-formate
• CAS: 161579-72-2
• 化学式: C₂₉H₃₈O₅
• 分子量: 466.618
• InChiKey: ZDWVCHOXORRLSK-RZJPGGONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (20R)-19-hydroxypregn-5-ene-3β,20-diyl 3-benzoate 20-formate 在 盐酸 、 sodium hydroxide 、 jones reagent 、 对甲苯磺酸 作用下， 以 吡啶 、 甲醇 、 乙醚 、 氯仿 、 丙酮 为溶剂， 反应 47.49h， 生成 (19E)-3β,17-dihydroxy-20-oxopregn-5-en-19-al 19-(O-carboxymethyl)oxime methylester
  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 对甲苯磺酸 、 lithium tri-t-butoxyaluminum hydride 、 锌 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 19.5h， 生成 (20R)-19-hydroxypregn-5-ene-3β,20-diyl 3-benzoate 20-formate
  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