(10S)-3β,17β-diacetoxy-5,10-secoandrostan-5-one | 929879-27-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (10S)-3β,17β-diacetoxy-5,10-secoandrostan-5-one
• CAS: 929879-27-6
• 化学式: C₂₃H₃₆O₅
• 分子量: 392.536
• InChiKey: ISHYGJIGNANIHU-UTISYCDMSA-N

反应信息

• 作为反应物：
  描述：

  (10S)-3β,17β-diacetoxy-5,10-secoandrostan-5-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以72%的产率得到(10S)-3β,17β-dihydroxy-5,10-secoandrostan-5-one
  参考文献：
  名称：

  Isolation and structure elucidation of new radical oxidation products of 5-hydroxy steroids

  摘要：

  Three new products have been isolated from the lead-tetraacetate version of the hypoiodite oxidation of 3 beta,17 beta-diacetoxy-5-hydroxy-5 alpha-androstane. Along with the expected 1(10)unsaturated 5,10-seco steroidal 5-ketones, the fragmentation reaction gave two epimeric C-4 iodides. Their structural assignment was based on X-ray data of one of them ((4R,10S)-4iodo-3 beta,17 beta-diacetoxy-5,10-secoandrostan-5-one). The third new product was found to be the 5 beta,6 beta-epoxide resulting from the dehydration of the tertiary alcohol followed by epoxidation of the intermediate Delta(5)-olefin. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.01.008
• 作为产物：
  描述：

  (4S,10S)-4-iodo-3β,17β-diacetoxy-5,10-secoandrostan-5-one 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以67%的产率得到(10S)-3β,17β-diacetoxy-5,10-secoandrostan-5-one
  参考文献：
  名称：

  Isolation and structure elucidation of new radical oxidation products of 5-hydroxy steroids

  摘要：

  Three new products have been isolated from the lead-tetraacetate version of the hypoiodite oxidation of 3 beta,17 beta-diacetoxy-5-hydroxy-5 alpha-androstane. Along with the expected 1(10)unsaturated 5,10-seco steroidal 5-ketones, the fragmentation reaction gave two epimeric C-4 iodides. Their structural assignment was based on X-ray data of one of them ((4R,10S)-4iodo-3 beta,17 beta-diacetoxy-5,10-secoandrostan-5-one). The third new product was found to be the 5 beta,6 beta-epoxide resulting from the dehydration of the tertiary alcohol followed by epoxidation of the intermediate Delta(5)-olefin. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.01.008

文献信息

• Synthesis of 5,10-seco analogs of testosterone
  作者：Vladimir A. Khripach、Vladimir N. Zhabinskii、Anna I. Kuchto、Yuliya Y. Zhiburtovich、Natalya B. Khripach、Alexander S. Lyakhov、Marinus B. Groen、Jaap van der Louw、Aede de Groot

  DOI：10.1016/j.steroids.2008.07.005

  日期：2008.12

  A number of 5,10-seco analogs of testosterone has been synthesized starting from products of the radical oxidation of 3 beta,17 beta-diacetoxy-5 alpha-androstan-5 alpha-ol. The obtained compounds possess a flexible 10-membered ring with substituents (=O, -OH) at C-3 and C-5. Similar derivatives with an (E)- and (Z)-Delta(1(10))-double bond have been prepared also. X-ray analysis and a combination of NMR experiments have been used for their structure elucidation and conformation analysis. (C) 2008 Published by Elsevier Inc.