(3S,5S)-5-[tert-butyl(dimethyl)silyl]oxydec-9-ene-1,3-diol | 936016-71-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3S,5S)-5-[tert-butyl(dimethyl)silyl]oxydec-9-ene-1,3-diol
• CAS: 936016-71-6
• 化学式: C₁₆H₃₄O₃Si
• 分子量: 302.53
• InChiKey: BKJWCKDZOOGICW-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,5S)-5-[tert-butyl(dimethyl)silyl]oxydec-9-ene-1,3-diol 、 [(Z,1R)-1-[(2R,3R)-3-methyl-6-phenylsulfanyl-3,4-dihydro-2H-pyran-2-yl]-6-tri(propan-2-yl)silyloxyhex-3-enoxy]-tri(propan-2-yl)silane 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以35%的产率得到[(2S)-1-[(4S,8R,9R)-8-[(Z,1R)-1,6-bis[tri(propan-2-yl)silyloxy]hex-3-enyl]-9-methyl-1,5,7-trioxaspiro[5.5]undecan-4-yl]hept-6-en-2-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  A Reductive Cyclization Approach to Attenol A

  摘要：

  A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.

  DOI：

  10.1021/jo0626459
• 作为产物：
  描述：

  (3S)-3-hydroxy-1-phenylmethoxydec-9-en-5-one 在 2,6-二甲基吡啶 、 氨 、 甲基锂 、 zirconium(IV) tert-butoxide 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 11.5h， 生成 (3S,5S)-5-[tert-butyl(dimethyl)silyl]oxydec-9-ene-1,3-diol
  参考文献：
  名称：

  A Reductive Cyclization Approach to Attenol A

  摘要：

  A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.

  DOI：

  10.1021/jo0626459

文献信息

• A Reductive Cyclization Approach to Attenol A
  作者：Thomas E. La Cruz、Scott D. Rychnovsky

  DOI：10.1021/jo0626459

  日期：2007.3.1

  A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.