[(1R,2'S,4S,4'R,6R,7S,8R,9R,10R,12S,13S,16S,18S)-10,16-diacetyloxy-4'-[tert-butyl(dimethyl)silyl]oxy-2',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-ene-6,5'-oxolane]-2'-yl]methyl acetate | 571185-89-2

• 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: [(1R,2'S,4S,4'R,6R,7S,8R,9R,10R,12S,13S,16S,18S)-10,16-diacetyloxy-4'-[tert-butyl(dimethyl)silyl]oxy-2',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-ene-6,5'-oxolane]-2'-yl]methyl acetate
• CAS: 571185-89-2
• 化学式: C₃₉H₆₂O₉Si
• 分子量: 703.001
• InChiKey: ASWFFTAPTIQCLF-SQJFOSMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  49
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(1R,2'S,4S,4'R,6R,7S,8R,9R,10R,12S,13S,16S,18S)-10,16-diacetyloxy-4'-[tert-butyl(dimethyl)silyl]oxy-2',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-ene-6,5'-oxolane]-2'-yl]methyl acetate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以99%的产率得到[(1R,2'S,4S,4'R,6S,7S,8R,9R,10R,12S,13S,16S,18S)-10,16-diacetyloxy-4'-[tert-butyl(dimethyl)silyl]oxy-2',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-ene-6,5'-oxolane]-2'-yl]methyl acetate
  参考文献：
  名称：

  New Oxidative Tools for the Functionalization of the Cephalostatin North 1 Hemisphere

  摘要：

  Dimethyldioxirane (DMDO) C-H oxidation of ketone 17 to hemiketal 18 (82%), bis-dehydration to vinyl ether 21 (77%), and DMDO again provides C-23 axial alcohol 23 (99%). Routine processing, Including a double-stereoselective Sharpless AD reaction (de >98%), gives alcohols 7 and 32. C-23 deoxy substrate 7 undergoes Suarez hypoiodite oxidative cyclization to (natural) beta spiroketal 34, but compound 32, bearing a C-23 silyl ether, generates unnatural spiroketal 33.

  DOI：

  10.1021/ol034551g
• 作为产物：
  描述：

  Acetic acid (2S,4aS,4bS,6R,6aR,6bR,7S,8S,9aS,10bR,12aS)-2-acetoxy-8-((R)-4-acetoxy-1,3-dihydroxy-3-methyl-butyl)-4a,6a,7-trimethyl-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,10b,11,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-6-yl ester 在 碘苯二乙酸 、 碘 、 三乙胺 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 6.0h， 生成 [(1R,2'S,4S,4'R,6R,7S,8R,9R,10R,12S,13S,16S,18S)-10,16-diacetyloxy-4'-[tert-butyl(dimethyl)silyl]oxy-2',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-ene-6,5'-oxolane]-2'-yl]methyl acetate
  参考文献：
  名称：

  New Oxidative Tools for the Functionalization of the Cephalostatin North 1 Hemisphere

  摘要：

  Dimethyldioxirane (DMDO) C-H oxidation of ketone 17 to hemiketal 18 (82%), bis-dehydration to vinyl ether 21 (77%), and DMDO again provides C-23 axial alcohol 23 (99%). Routine processing, Including a double-stereoselective Sharpless AD reaction (de >98%), gives alcohols 7 and 32. C-23 deoxy substrate 7 undergoes Suarez hypoiodite oxidative cyclization to (natural) beta spiroketal 34, but compound 32, bearing a C-23 silyl ether, generates unnatural spiroketal 33.

  DOI：

  10.1021/ol034551g