(8β)-(20R)-des-A,B-18,20-epoxy-25-[(methoxymethyl)oxy]-21-norcholestan-8-one | 442200-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (8β)-(20R)-des-A,B-18,20-epoxy-25-[(methoxymethyl)oxy]-21-norcholestan-8-one
• 英文别名: (3R,3aS,5aR,9aS)-3-[4-(methoxymethoxy)-4-methylpentyl]-3,3a,4,5,5a,7,8,9-octahydro-1H-indeno[1,7a-c]furan-6-one
• CAS: 442200-83-1
• 化学式: C₁₉H₃₂O₄
• 分子量: 324.461
• InChiKey: ZQYQYYQIOQUFFN-BUIAKZPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8β)-(20R)-des-A,B-18,20-epoxy-25-[(methoxymethyl)oxy]-21-norcholestan-8-one 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 47.0h， 生成 (5Z,7E)-(1S,3R,20R)-18,20-epoxy-21-nor-9,10-secocholesta-5,7,10(19)-trien-1,3,25-triol
  参考文献：
  名称：

  Synthesis of New 18-Substituted Analogues of Calcitriol Using a Photochemical Remote Functionalization

  摘要：

  A novel convergent synthetic approach to new analogues of calcitriol modified at the C-18 position is reported. The key step in the synthesis is the 20-hydroxyl-directed photochemical iodination of the 18-methyl group in the presence of (diacetoxyiodo)benzene. Using this methodology, two new analogues of calcitriol were prepared: the first contains a hydroxylated alkyl side chain attached at C-18 with the natural side chain replaced by an isopropylidene group; the second is a conformationally locked analogue due to an extra oxacycle between the C-18 and C-20 positions.

  DOI：

  10.1021/jo020022z
• 作为产物：
  描述：

  (8β)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18-iodo-21-norcholest-24-en-20-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 重铬酸吡啶 、 mercury(II) diacetate 、 四丁基氟化铵 、 silver(I) acetate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 206.75h， 生成 (8β)-(20R)-des-A,B-18,20-epoxy-25-[(methoxymethyl)oxy]-21-norcholestan-8-one
  参考文献：
  名称：

  Synthesis of New 18-Substituted Analogues of Calcitriol Using a Photochemical Remote Functionalization

  摘要：

  A novel convergent synthetic approach to new analogues of calcitriol modified at the C-18 position is reported. The key step in the synthesis is the 20-hydroxyl-directed photochemical iodination of the 18-methyl group in the presence of (diacetoxyiodo)benzene. Using this methodology, two new analogues of calcitriol were prepared: the first contains a hydroxylated alkyl side chain attached at C-18 with the natural side chain replaced by an isopropylidene group; the second is a conformationally locked analogue due to an extra oxacycle between the C-18 and C-20 positions.

  DOI：

  10.1021/jo020022z

文献信息

• Synthesis of New 18-Substituted Analogues of Calcitriol Using a Photochemical Remote Functionalization
  作者：Iván Cornella、José Pérez Sestelo、Antonio Mouriño、Luis A. Sarandeses

  DOI：10.1021/jo020022z

  日期：2002.7.1

  A novel convergent synthetic approach to new analogues of calcitriol modified at the C-18 position is reported. The key step in the synthesis is the 20-hydroxyl-directed photochemical iodination of the 18-methyl group in the presence of (diacetoxyiodo)benzene. Using this methodology, two new analogues of calcitriol were prepared: the first contains a hydroxylated alkyl side chain attached at C-18 with the natural side chain replaced by an isopropylidene group; the second is a conformationally locked analogue due to an extra oxacycle between the C-18 and C-20 positions.