(13S,14R)-14-hydroxy-6β-methoxy-17-trimethylsilyloxy-3α,5-cyclo-13,14-seco-5α-androstan-17-carbonitrile | 775355-44-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (13S,14R)-14-hydroxy-6β-methoxy-17-trimethylsilyloxy-3α,5-cyclo-13,14-seco-5α-androstan-17-carbonitrile
• CAS: 775355-44-7
• 化学式: C₂₄H₄₁NO₃Si
• 分子量: 419.68
• InChiKey: SJBLOTOZYPTOLM-REDNPOQOSA-N

反应信息

• 作为反应物：
  描述：

  (13S,14R)-14-hydroxy-6β-methoxy-17-trimethylsilyloxy-3α,5-cyclo-13,14-seco-5α-androstan-17-carbonitrile 在 Pd-BaSO₄ 吡啶 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 氢氧化钾 、 氯化亚砜 、 四丁基氟化铵 、 氢气 、 aluminum isopropoxide 、 L-Selectride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 乙醇 、 水 、 环己酮 、 甲苯 为溶剂， 反应 19.08h， 生成 (13S)-13,14-seco-androst-4-en-3,17-dione
  参考文献：
  名称：

  Synthesis of 13,14-secotestosterone derivatives

  摘要：

  A number of testosterone analogs with a 13,14-secosteroidal fragment have been prepared from (13S)-13-iodo-6beta-methoxy-3alpha, 5-cyclo-13,14-seco-5alpha-androstan-14,17-dione. The key steps involved stereoselective deiodination of the starting compound with triphenylphosphine and selective protection of the 17-keto group with trimethylsilylcyanide. Removal of iodine at C-13 proceeded with inversion of the configuration at C-13, which has been established by X-ray crystallography. 13,14-Secotestosterone analogues substituted and non-substituted at C-14 have been prepared. The obtained compounds containing flexible CD ring fragments are of great interest for comparative studies in biological tests together with testosterone and other steroids with a rigid tetracyclic skeleton. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.04.010
• 作为产物：
  描述：

  (13S)-6β-methoxy-3α,5-cyclo-13,14-seco-5α-androsta-14,17-dione 在 sodium tetrahydroborate 、 三苯基膦 、 calcium chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 16.08h， 生成 (13S,14R)-14-hydroxy-6β-methoxy-17-trimethylsilyloxy-3α,5-cyclo-13,14-seco-5α-androstan-17-carbonitrile
  参考文献：
  名称：

  Synthesis of 13,14-secotestosterone derivatives

  摘要：

  A number of testosterone analogs with a 13,14-secosteroidal fragment have been prepared from (13S)-13-iodo-6beta-methoxy-3alpha, 5-cyclo-13,14-seco-5alpha-androstan-14,17-dione. The key steps involved stereoselective deiodination of the starting compound with triphenylphosphine and selective protection of the 17-keto group with trimethylsilylcyanide. Removal of iodine at C-13 proceeded with inversion of the configuration at C-13, which has been established by X-ray crystallography. 13,14-Secotestosterone analogues substituted and non-substituted at C-14 have been prepared. The obtained compounds containing flexible CD ring fragments are of great interest for comparative studies in biological tests together with testosterone and other steroids with a rigid tetracyclic skeleton. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.04.010