3β-acetoxy-17β-p-toluenesulfonyloxy-5α-androstan | 17291-39-3

• 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: 3β-acetoxy-17β-p-toluenesulfonyloxy-5α-androstan
• 英文别名: 3β-acetoxy-17β-(tosyloxy)-5α-androstane；3β-acetoxy-17β-(toluene-4-sulfonyloxy)-5α-androstane；3β-Acetoxy-17β-(toluol-4-sulfonyloxy)-5α-androstan；17β-(p-Toluolsulfonyloxy)-3β-acetoxy-5α-androstan；[(3S,5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-17-(4-methylphenyl)sulfonyloxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 17291-39-3
• 化学式: C₂₈H₄₀O₅S
• 分子量: 488.689
• InChiKey: CUWKQFNAIRRVLQ-HBPNSXOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-17β-p-toluenesulfonyloxy-5α-androstan 在 溴乙烷 、 magnesium 作用下， 以 乙醚 、 苯 为溶剂， 生成 17-methyl-18-nor-5α-androst-13(17)-en-3β-ol
  参考文献：
  名称：

  Favorskii rearrangements of .alpha.-halogenated acetylcycloalkanes. 4. Stereochemistry of cyclopropanonic rearrangements and the influence of steric factors on the competing formation of .alpha.-hydroxy ketones

  摘要：

  DOI：

  10.1021/jo00160a004
• 作为产物：
  描述：

  醋酸去氢表雄酮 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 为溶剂， 反应 102.0h， 生成 3β-acetoxy-17β-p-toluenesulfonyloxy-5α-androstan
  参考文献：
  名称：

  Favorskii rearrangements of .alpha.-halogenated acetylcycloalkanes. 4. Stereochemistry of cyclopropanonic rearrangements and the influence of steric factors on the competing formation of .alpha.-hydroxy ketones

  摘要：

  DOI：

  10.1021/jo00160a004

文献信息

• Axial and equatorial thiols—III
  作者：D.A. Swann、J.H. Turnbull

  DOI：10.1016/0040-4020(68)88096-2

  日期：1968.1

  17α and 17β-mercaptoandrostanes and androstan-3β-ols have been prepared as examples of axial and equatorial thiol epimers in trans-fused 5-membered fixed ring systems. The conformation of the epimers has been established by PMR measurements.

  17α和17β-mercaptoandrostanes和雄甾烷3β-醇已被制备的实施例的轴向和赤道硫醇差向异构体中的反式-融合5元固定环系统。差向异构体的构象已通过PMR测量确定。
• Madaewa, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 2573,2577; engl. Ausg. S. 2630, 2633
  作者：Madaewa

  DOI：——

  日期：——
• Practical synthesis of androgen: the efficient transformation of 17-oxo group to 17α-hydroxy group
  作者：Tetsuo Ohta、Huyue Zhang、Yoshitaka Torihara、Takemasa Hida、Isao Furukawa

  DOI：10.1016/s0039-128x(98)00067-1

  日期：1998.12

  The present report describes the improved transformation of the 17-oxo group in 3 beta-acetoxy-5 alpha-androstan-17-one to a 17 alpha-hydroxy group. A mixture of 17 alpha-acetoxy and 16-ene compounds, which are usually produced by the standard synthetic route, were treated with peracetic acid (epoxidation of the 16-ene compound) and then sodium hydroxide (reduction-hydrolysis) to give the desired 17 alpha-hydroxy compound in much better yield than that in previous reports. Recrystallization of the crude product with cyclohexane-methanol gave the pure compound in 54% yield (total yield from starting ketone). (Steroids 63:630-632). (C) 1998 by Elsevier Science Inc.
• Hypocholesterolemic agents. 7. C-17 epimer of 20,25-diazacholesterol
  作者：Raymond E. Counsell、V. V. Ranade、Fortune Kohen

  DOI：10.1021/jm00283a010

  日期：1971.1