(1"S,2S,2'R,6'R,8'S,9'S,11'R)-4-<8'-<1'-<<(tert-Butyldiphenylsilyl)oxy>methyl>propyl>-9',11'-dimethyl-1',7'-dioxaspiro<5.5>undec-4'-en-2'-yl>-2-hydroxy-2-methylbutan-1-yl p-toluenesulfonate | 143924-92-9

• 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: (1"S,2S,2'R,6'R,8'S,9'S,11'R)-4-<8'-<1'-<<(tert-Butyldiphenylsilyl)oxy>methyl>propyl>-9',11'-dimethyl-1',7'-dioxaspiro<5.5>undec-4'-en-2'-yl>-2-hydroxy-2-methylbutan-1-yl p-toluenesulfonate
• 英文别名: (1"S,2S,2'R,6'R,8'S,9'S,11'R)-4-[8'-(1'-{[(tert-Butyldiphenylsilyl)oxy]methyl}propyl)-9',11'-dimethyl-1',7'-dioxaspiro[5.5]undec-4'-en-2'-yl]-2-hydroxy-2-methylbutan-1-yl p-toluenesulfonate；[(2S)-4-[(2S,3S,5R,6R,8R)-2-[(2S)-1-[tert-butyl(diphenyl)silyl]oxybutan-2-yl]-3,5-dimethyl-1,7-dioxaspiro[5.5]undec-10-en-8-yl]-2-hydroxy-2-methylbutyl] 4-methylbenzenesulfonate
• CAS: 143924-92-9；144015-91-8
• 化学式: C₄₃H₆₀O₇SSi
• 分子量: 749.097
• InChiKey: LCZMNKQOAGPGHP-NEOWBCAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.94
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1"S,2S,2'R,6'R,8'S,9'S,11'R)-4-<8'-<1'-<<(tert-Butyldiphenylsilyl)oxy>methyl>propyl>-9',11'-dimethyl-1',7'-dioxaspiro<5.5>undec-4'-en-2'-yl>-2-hydroxy-2-methylbutan-1-yl p-toluenesulfonate 在 碘苯二乙酸 、 三氟化硼乙醚 、 四丁基氟化铵 、 碘 、 sodium hydride 、 lithium iodide 作用下， 以 四氢呋喃 、 环己烷 、 paraffin 为溶剂， 反应 2.5h， 生成 (2S,2'S,5'S,7'S,9'S,10'S,12'R)-2-(2'-(Iodomethyl)-2',10',12'-trimethyl-1',6',8'-trioxadispiro<4.1.5.3>pentadec-13'-en-9'-yl)butan-1-ol
  参考文献：
  名称：

  Synthesis of the bis-spiroacetal moiety of 17-epi-20-deoxysalinomycin

  摘要：

  The synthesis of the bis-spiroacetal moiety of 17-epi-20-deoxysalinomycin (4) is reported in which the key step involves oxidative cyclization of the hydroxy spiroacetals 14 and 15 to the bis-spiroacetals 16 and 17 using (diacetoxyiodo)benzene and iodine under photolytic conditions.

  DOI：

  10.1021/jo00048a009
• 作为产物：
  描述：

  [(2S)-8-[(3R,5S,6S)-6-[(2S)-1-[tert-butyl(diphenyl)silyl]oxybutan-2-yl]-2-methoxy-3,5-dimethyloxan-2-yl]-2-methyl-2,5-bis(trimethylsilyloxy)oct-7-ynyl] 4-methylbenzenesulfonate 在 Lindlar's catalyst 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 5.2h， 生成 (1"S,2S,2'R,6'R,8'S,9'S,11'R)-4-<8'-<1'-<<(tert-Butyldiphenylsilyl)oxy>methyl>propyl>-9',11'-dimethyl-1',7'-dioxaspiro<5.5>undec-4'-en-2'-yl>-2-hydroxy-2-methylbutan-1-yl p-toluenesulfonate
  参考文献：
  名称：

  Synthesis of the bis-spiroacetal moiety of 17-epi-20-deoxysalinomycin

  摘要：

  The synthesis of the bis-spiroacetal moiety of 17-epi-20-deoxysalinomycin (4) is reported in which the key step involves oxidative cyclization of the hydroxy spiroacetals 14 and 15 to the bis-spiroacetals 16 and 17 using (diacetoxyiodo)benzene and iodine under photolytic conditions.

  DOI：

  10.1021/jo00048a009

文献信息

• Synthesis of the bis-spiroacetal moiety of 17-epi-20-deoxysalinomycin
  作者：Margaret A. Brimble、Geoffrey M. Williams

  DOI：10.1021/jo00048a009

  日期：1992.10

  The synthesis of the bis-spiroacetal moiety of 17-epi-20-deoxysalinomycin (4) is reported in which the key step involves oxidative cyclization of the hydroxy spiroacetals 14 and 15 to the bis-spiroacetals 16 and 17 using (diacetoxyiodo)benzene and iodine under photolytic conditions.