4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane | 251906-74-8

• 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: 4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane
• 英文别名: [(3R,5S,6R,7R,8S,9S,10R,13R,14S,17R)-6,7-diacetyloxy-10,13-dimethyl-17-[(2R)-4-tri(propan-2-yl)silyloxybutan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] 2-(4-benzoylphenyl)acetate
• CAS: 251906-74-8
• 化学式: C₅₁H₇₄O₈Si
• 分子量: 843.229
• InChiKey: HKDMJHHLZYQHFU-PPVZVASXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.33
• 重原子数：
  60
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane 在 pyridinium chlorochromate 作用下， 以63%的产率得到[(3R,5S,6R,7R,8R,9S,10R,13R,17R)-6,7-diacetyloxy-10,13-dimethyl-17-[(2R)-4-tri(propan-2-yl)silyloxybutan-2-yl]-2,3,4,5,6,7,8,9,11,12,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 2-(4-benzoylphenyl)acetate
  参考文献：
  名称：

  First Total Synthesis of Xestobergsterol A and Active Structural Analogues of the Xestobergsterols¹

  摘要：

  [GRAPHICS]A novel pentacyclic polyhydroxylated sterol, xestobergsterol A (la), has been synthesized in 24 steps and in good overall yield from stigmasterol 17. The key steps of the synthesis are the Breslow remote functionalization of the polyoxygenated steroid derived from 25 and the base-catalyzed epimerization-aldol condensation of the dione derived from 27.

  DOI：

  10.1021/ol991057x
• 作为产物：
  描述：

  3β,6α,7β,23-tetraacetoxy-5α-24-norcholane 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane
  参考文献：
  名称：

  First total synthesis of xestobergsterol A and active structural analogues of the xestobergsterols

  摘要：

  The novel pentacyclic polyhydroxylated sterol, xestobergsterol A la, a strong inhibitor of histamine release from rat mast cells induced by anti-IgE, has been synthesized in 24 steps and good overall yield From stigmasterol 7. The Breslow remote functionalization process has been extended to several more highly functionalized steroid derivatives, especially those with oxygen functionality in the B-ring. The key steps of the synthesis of xestobergsterol A la and its analogues, 7-deoxyxestobergsterol A Id and 16,23-seco-23-deoxyxestobergsterol A 73, are the Breslow remote functionalization of oxygenated steroids and for compounds la and Id, a novel base-catalyzed epimerization-aldol condensation of a dione to give the desired CD-cis ring structure of the xestobergsterols. Thus the known alcohol 75, prepared from stigmasterol 7, was taken to the tetraacetate 107 which was then converted via a Breslow remote functionalization into the alkene aldehyde 114 which was transformed in 5 steps to xestobergsterol A la. Testing of the synthetic materials showed that the two analogues, 7-deoxyxestobergsterol A Ib and 16,23-seco-23-deoxyxestobergsterol A 73, are also potent inhibitors of histamine release with ICS, values (IC50 500 nM and 750 nM, respectively) being only 1015 times less than that of xestobergsterol A itself (50 nM). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01086-3