3-[(8R,9S,13S,14S,16R,17S)-3,17-bis[[tert-butyl(dimethyl)silyl]oxy]-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]propanoyl chloride | 625387-79-3

• 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: 3-[(8R,9S,13S,14S,16R,17S)-3,17-bis[[tert-butyl(dimethyl)silyl]oxy]-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]propanoyl chloride
• CAS: 625387-79-3
• 化学式: C₃₃H₅₅ClO₃Si₂
• 分子量: 591.422
• InChiKey: AMNPDFJAYQTGNA-ZCMKSVQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.09
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(8R,9S,13S,14S,16R,17S)-3,17-bis[[tert-butyl(dimethyl)silyl]oxy]-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]propanoyl chloride 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.92h， 生成
  参考文献：
  名称：

  Synthesis of a First Estradiol-Adenosine Hybrid Compound

  摘要：

  An estradiol derivative, bearing an adenosine residue linked at C-16alpha by a three-carbon side chain, provides access to a new series of substrate-cofactor hybrid compound designed to potentially interact with two binding domains of the enzyme type 1 17alpha-hydroxysteroid dehydrogenase (17beta-HSD). The synthesis of 5'-O-[3-(3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl)propanoyl]adenosine (7) is reported focusing on the crucial last steps: the coupling of adenosine residue to estradiol side chain by an ester link and the appropriate final cleavage of three protecting groups.

  DOI：

  10.1081/scc-120023440
• 作为产物：
  描述：

  3-<3',17'β-di-(tert-butyldimethylsilyloxy)-1',3',5'(10')-estratrien-16'α-yl>propanol 在 jones' reagent 、 草酰氯 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.33h， 生成 3-[(8R,9S,13S,14S,16R,17S)-3,17-bis[[tert-butyl(dimethyl)silyl]oxy]-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]propanoyl chloride
  参考文献：
  名称：

  Synthesis of a First Estradiol-Adenosine Hybrid Compound

  摘要：

  An estradiol derivative, bearing an adenosine residue linked at C-16alpha by a three-carbon side chain, provides access to a new series of substrate-cofactor hybrid compound designed to potentially interact with two binding domains of the enzyme type 1 17alpha-hydroxysteroid dehydrogenase (17beta-HSD). The synthesis of 5'-O-[3-(3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl)propanoyl]adenosine (7) is reported focusing on the crucial last steps: the coupling of adenosine residue to estradiol side chain by an ester link and the appropriate final cleavage of three protecting groups.

  DOI：

  10.1081/scc-120023440

文献信息

• Synthesis of a First Estradiol-Adenosine Hybrid Compound
  作者：Donald Poirier、Roch P. Boivin、Marie Bérubé、Sheng-Xiang Lin

  DOI：10.1081/scc-120023440

  日期：2003.9

  An estradiol derivative, bearing an adenosine residue linked at C-16alpha by a three-carbon side chain, provides access to a new series of substrate-cofactor hybrid compound designed to potentially interact with two binding domains of the enzyme type 1 17alpha-hydroxysteroid dehydrogenase (17beta-HSD). The synthesis of 5'-O-[3-(3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl)propanoyl]adenosine (7) is reported focusing on the crucial last steps: the coupling of adenosine residue to estradiol side chain by an ester link and the appropriate final cleavage of three protecting groups.