9β,11β-epoxy-17α-hydroxy-17β-(4-(R)-hydroxy-2,2-dioxido-1,2-oxathiolan-4-yl)-16α-methylandrosta-1,4-diene-3-one | 223776-51-0

• 分子结构分类: 有机化合物
• 英文名称: 9β,11β-epoxy-17α-hydroxy-17β-(4-(R)-hydroxy-2,2-dioxido-1,2-oxathiolan-4-yl)-16α-methylandrosta-1,4-diene-3-one
• 英文别名: (1S,2S,10S,11S,13R,14R,15S,17S)-14-hydroxy-14-[(4R)-4-hydroxy-2,2-dioxooxathiolan-4-yl]-2,13,15-trimethyl-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadeca-3,6-dien-5-one
• CAS: 223776-51-0
• 化学式: C₂₃H₃₀O₇S
• 分子量: 450.553
• InChiKey: RNQLUTKABKBIPP-BCYPZBMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9β,11β-epoxy-17α-hydroxy-17β-(4-(R)-hydroxy-2,2-dioxido-1,2-oxathiolan-4-yl)-16α-methylandrosta-1,4-diene-3-one 在 盐酸 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 糠酸莫米松杂质
  参考文献：
  名称：

  Unusual hydroxy-?-sultone byproducts of steroid 21-methanesulfonylation. An efficient synthesis of mometasone 17-furoate (Sch 32088)

  摘要：

  An efficient two stage synthesis of the steroid anti-inflammatory agent mometasone 17-furoate (Sch 32088) 4 from 17 alpha,21-dihydroxy-16 alpha-methyl-9 beta,11 beta-oxidopregna-1,4-diene-3,20-dione 6 is described and the structures of unusual delta-hydroxy-gamma-sultone byproducts of 4-dimethylaminopyridine catalyzed methanesulfonylation of 21-hydroxy-20-ketosteroids are deduced. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01146-6
• 作为产物：
  描述：

  地塞米松环氧水解物 在 4-二甲氨基吡啶 、 甲基磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以69%的产率得到21-氯-9-beta,11-beta-环氧-17-羟基-16-alpha-甲基孕甾-1,4-二烯-3,20-二酮
  参考文献：
  名称：

  Unusual hydroxy-?-sultone byproducts of steroid 21-methanesulfonylation. An efficient synthesis of mometasone 17-furoate (Sch 32088)

  摘要：

  An efficient two stage synthesis of the steroid anti-inflammatory agent mometasone 17-furoate (Sch 32088) 4 from 17 alpha,21-dihydroxy-16 alpha-methyl-9 beta,11 beta-oxidopregna-1,4-diene-3,20-dione 6 is described and the structures of unusual delta-hydroxy-gamma-sultone byproducts of 4-dimethylaminopyridine catalyzed methanesulfonylation of 21-hydroxy-20-ketosteroids are deduced. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01146-6