17β-(2,2-dioxido-3,4-dehydro-1,2-oxathiolan-4-yl)-9β,11β-epoxy-17α-hydroxy-16α-methylandrosta-1,4-dien-3-one 17-(2-furoate) | 223776-50-9

• 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: 17β-(2,2-dioxido-3,4-dehydro-1,2-oxathiolan-4-yl)-9β,11β-epoxy-17α-hydroxy-16α-methylandrosta-1,4-dien-3-one 17-(2-furoate)
• 英文别名: (9beta,11beta,16alpha,17alphalpha)-17-(2,2-Dioxido-5H-1,2-oxathiol-4-yl)-9,11-epoxy-17-[(2-furanylcarbonyl)oxy]-16-methyl-androsta-1,4-dien-3-one；[(1S,2S,10S,11S,13R,14R,15S,17S)-14-(2,2-dioxo-5H-oxathiol-4-yl)-2,13,15-trimethyl-5-oxo-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadeca-3,6-dien-14-yl] furan-2-carboxylate
• CAS: 223776-50-9
• 化学式: C₂₈H₃₀O₈S
• 分子量: 526.607
• InChiKey: WMAGSHQFHXSDSB-VOEDJRENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  17β-(2,2-dioxido-3,4-dehydro-1,2-oxathiolan-4-yl)-9β,11β-epoxy-17α-hydroxy-16α-methylandrosta-1,4-dien-3-one 17-(2-furoate) 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以87%的产率得到糠酸莫米松杂质
  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 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 17β-(2,2-dioxido-3,4-dehydro-1,2-oxathiolan-4-yl)-9β,11β-epoxy-17α-hydroxy-16α-methylandrosta-1,4-dien-3-one 17-(2-furoate)
  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

文献信息

• Unusual hydroxy-?-sultone byproducts of steroid 21-methanesulfonylation. An efficient synthesis of mometasone 17-furoate (Sch 32088)
  作者：Richard W. Draper、Bin Hu、Andrew T. McPhail、Mohindar S. Puar、Eugene J. Vater、Lois Weber

  DOI：10.1016/s0040-4020(98)01146-6

  日期：1999.3

  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.