(1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Hydroxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]decan-5-ol | 137647-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Hydroxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]decan-5-ol
• CAS: 137647-82-6
• 化学式: C₂₂H₄₂O₆Si
• 分子量: 430.657
• InChiKey: SZHSEQVFNUAFPY-JUAQWZRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.68
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Hydroxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]decan-5-ol 在 chromium chloride 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 36.0h， 生成 1-(2,4-Dimethoxy-benzyl)-3-[(2E,4E)-(S)-6-((1R,2R,4S,6R,7S,8S)-1,7-dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-1-hydroxy-4-methyl-hepta-2,4-dien-(Z)-ylidene]-pyrrolidine-2,4-dione
  参考文献：
  名称：

  A total synthesis of (.+-.)-tirandamycin B

  摘要：

  The total synthesis of the dienoyl tetramic acid antibiotic (+/-)-tirandamycin B is described. The key transformations of the strategy include (1) cyclization of pyranone 14 with fluorosilicic acid to provide the 2,6-dioxabicyclo[3.3.1]nonane system of the natural product, (2) reductive removal of the benzyl ether from enone 15, and (3) attachment of the tetramic acid moiety by using the Schlessinger phosphonate protocol. Protection of the primary hydroxyl function of tirandamycin B as the triisopropylsilyl (TIPS) ether was crucial to the success of the strategy.

  DOI：

  10.1021/ja00023a029
• 作为产物：
  描述：

  (1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]decan-5-ol 在 di(tert-butyl)-biphenyl 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到(1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Hydroxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]decan-5-ol
  参考文献：
  名称：

  A total synthesis of (.+-.)-tirandamycin B

  摘要：

  The total synthesis of the dienoyl tetramic acid antibiotic (+/-)-tirandamycin B is described. The key transformations of the strategy include (1) cyclization of pyranone 14 with fluorosilicic acid to provide the 2,6-dioxabicyclo[3.3.1]nonane system of the natural product, (2) reductive removal of the benzyl ether from enone 15, and (3) attachment of the tetramic acid moiety by using the Schlessinger phosphonate protocol. Protection of the primary hydroxyl function of tirandamycin B as the triisopropylsilyl (TIPS) ether was crucial to the success of the strategy.

  DOI：

  10.1021/ja00023a029