(1S,2R,5S,6R,8R,9R,11R)-11-[2-(benzenesulfonyl)ethyl]-5-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6,10,10-trimethyl-12-oxo-13-oxatricyclo[6.4.1.01,6]tridecane-9-carbonitrile | 166533-83-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R,5S,6R,8R,9R,11R)-11-[2-(benzenesulfonyl)ethyl]-5-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6,10,10-trimethyl-12-oxo-13-oxatricyclo[6.4.1.01,6]tridecane-9-carbonitrile
• CAS: 166533-83-1
• 化学式: C₃₇H₆₁NO₆SSi₂
• 分子量: 704.131
• InChiKey: RNMKXUBZLZNFRC-YXZCGSBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.57
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2R,5S,6R,8R,9R,11R)-11-[2-(benzenesulfonyl)ethyl]-5-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6,10,10-trimethyl-12-oxo-13-oxatricyclo[6.4.1.01,6]tridecane-9-carbonitrile 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,2R,5S,6R,8R,9S,11R)-11-(2-Benzenesulfonyl-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,10,10-trimethyl-12-oxo-13-oxa-tricyclo[6.4.1.0^1,6]tridecane-9-carbaldehyde
  参考文献：
  名称：

  New Strategy for the Synthesis of the Taxane Diterpenes: Formation of the A-Ring and Introduction of the C-1 Hydroxyl Group

  摘要：

  DOI：

  10.1016/00404-0399(50)1084u-
• 作为产物：
  描述：

  (benzenesulfonyl)methyllithium 、 以 四氢呋喃 为溶剂， 生成 (1S,2R,5S,6R,8R,9R,11R)-11-[2-(benzenesulfonyl)ethyl]-5-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6,10,10-trimethyl-12-oxo-13-oxatricyclo[6.4.1.01,6]tridecane-9-carbonitrile
  参考文献：
  名称：

  New Strategy for the Synthesis of the Taxane Diterpenes: Formation of the A-Ring and Introduction of the C-1 Hydroxyl Group

  摘要：

  DOI：

  10.1016/00404-0399(50)1084u-

文献信息

• Taxane diterpenes 4: Autoxidation, epimerization and isomerization for the introduction of functionality into the taxane ABC ring system
  作者：Philip Magnus、Feroze Ujjainwalla、Nicholas Westwood、Vince Lynch

  DOI：10.1016/s0040-4020(98)00056-8

  日期：1998.3

  The bicyclo[5.4.0]undecenone 4 was converted through a four step sequence involving activation, gem-methylcyclopropanation and reductive cleavage into 18 alpha/beta, containing the B/C rings of the taxanes. The A-ring has been attached to the B/C ring system by cyclization of the sulfone-ester 23 alpha to give 24. The A-ring was modified to give 29, which underwent beta-elimination of the 3,10-oxido bridge via a dianion, followed by transannular hydride shift to give the butenolide 30 and 32. Autoxidation of 30 gave 33 which was further elaborated into the trans-fused B/C adduct 35. The isomeric 3,10-diones trans-39 and cis-45 undergo autoxidation using t-BuOK/THF/O-2/P(OEt)(3) to give 2 and 46 respectively without B/C cis/trans isomerization. (C) 1998 Elsevier Science Ltd. All rights reserved.
• New Strategy for the Synthesis of the Taxane Diterpenes: Formation of the A-Ring and Introduction of the C-1 Hydroxyl Group
  作者：P Magnus

  DOI：10.1016/00404-0399(50)1084u-

  日期：1995.7.24