19-(tert-butyldimethylsiloxy)-17,17-ethylenedioxy-7-oxoandrost-5-en-3β-yl acetate | 213695-73-9

• 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: 19-(tert-butyldimethylsiloxy)-17,17-ethylenedioxy-7-oxoandrost-5-en-3β-yl acetate
• CAS: 213695-73-9
• 化学式: C₂₉H₄₆O₆Si
• 分子量: 518.766
• InChiKey: HHGDCSCJIFGTFP-FQLNSKJBSA-N

反应信息

• 作为反应物：
  描述：

  19-(tert-butyldimethylsiloxy)-17,17-ethylenedioxy-7-oxoandrost-5-en-3β-yl acetate 在 吡啶 、 chromium(VI) oxide 、 甲醇 、 sodium hydroxide 、 四丁基氟化铵 、 双氧水 、 L-Selectride 、 magnesium sulfate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 262.66h， 生成 (19E)-3β,7α-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime
  参考文献：
  名称：

  Synthesis of (19E)-3β,7α-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, a new hapten for 7α-hydroxydehydroepiandrosterone(3β,7α-dihydroxyandrost-5-en-17-one)

  摘要：

  The title compound was prepared in 11 steps from 17, 17-ethylenedioxy-19-hydroxyandrost-5-en-3 beta-yl acetate. After tert-butyldimethylsilyl protection of the the 19-hydroxyl group, a 7-oxo group was introduced by oxidation with 3, 5-dimethylpyrazole-chromium trioxide complex, and then selectively reduced with L-Selectride(R) to give a 7 alpha-hydroxy derivative. This partially protected triol was acetylated and desilylated to 3, 7-diacetate. Subsequent oxidation with pyridine-chromium trioxide complex gave 19-aldehyde, which was transformed into the corresponding protected 19-(O-carboxymethyl)oxime. Successive ketal cleavage, deacetylation, and methyl ester splitting gave the Sinal (19E)-3 beta, 7 alpha-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, designed as a hapten for 7 alpha-hydroxydehydroepiandrosterone immunoassays. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00047-6
• 作为产物：
  描述：

  19-(tert-butyldimethylsiloxy)-17,17-ethylenedioxyandrost-5-en-3β-yl acetate 在 3,5-二甲基吡唑 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以64%的产率得到19-(tert-butyldimethylsiloxy)-17,17-ethylenedioxy-7-oxoandrost-5-en-3β-yl acetate
  参考文献：
  名称：

  Synthesis of (19E)-3β,7α-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, a new hapten for 7α-hydroxydehydroepiandrosterone(3β,7α-dihydroxyandrost-5-en-17-one)

  摘要：

  The title compound was prepared in 11 steps from 17, 17-ethylenedioxy-19-hydroxyandrost-5-en-3 beta-yl acetate. After tert-butyldimethylsilyl protection of the the 19-hydroxyl group, a 7-oxo group was introduced by oxidation with 3, 5-dimethylpyrazole-chromium trioxide complex, and then selectively reduced with L-Selectride(R) to give a 7 alpha-hydroxy derivative. This partially protected triol was acetylated and desilylated to 3, 7-diacetate. Subsequent oxidation with pyridine-chromium trioxide complex gave 19-aldehyde, which was transformed into the corresponding protected 19-(O-carboxymethyl)oxime. Successive ketal cleavage, deacetylation, and methyl ester splitting gave the Sinal (19E)-3 beta, 7 alpha-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, designed as a hapten for 7 alpha-hydroxydehydroepiandrosterone immunoassays. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00047-6