(1S,4aS,13aR)-6-(tert-Butyl-dimethyl-silanyloxy)-9,9-diethoxy-1,4a,7-trimethyl-1,2,3,4,4a,7,9,10,11,12,13,13a-dodecahydro-8-oxa-9-sila-cyclohepta[a]phenanthrene-1-carboxylic acid methyl ester | 287919-41-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,4aS,13aR)-6-(tert-Butyl-dimethyl-silanyloxy)-9,9-diethoxy-1,4a,7-trimethyl-1,2,3,4,4a,7,9,10,11,12,13,13a-dodecahydro-8-oxa-9-sila-cyclohepta[a]phenanthrene-1-carboxylic acid methyl ester
• CAS: 287919-41-9
• 化学式: C₃₂H₅₄O₆Si₂
• 分子量: 590.948
• InChiKey: ZWUQPARLGULUNT-SYZHUBDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,4aS,13aR)-6-(tert-Butyl-dimethyl-silanyloxy)-9,9-diethoxy-1,4a,7-trimethyl-1,2,3,4,4a,7,9,10,11,12,13,13a-dodecahydro-8-oxa-9-sila-cyclohepta[a]phenanthrene-1-carboxylic acid methyl ester 在 potassium fluoride 、 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Functionalisation of Alkylalkoxysilanes. Studies Towards Annulations of Diterpenoids

  摘要：

  Ortho-(2-triethoxysilylethyl) derivatives of aryl ketones undergo oxidative desilylation with H2O2. Tetralone derivatives have served as model substrates for 14-2-(triethoxysilylethyl)-7-oxopodocarpanes, which have been converted into 2-arylethanols in a four-step sequence (BH3. BMS, H2O2, Et3SiH/CF3COOH, TBAF) without isolation of intermediate products (oxasilepin, diol, trifluoroacetate). Use of the 14-(2-diethoxysilylmethyl) analogue improved the overall yield significantly (75 versus 40%). Re-oxidation of ring B with CAN gave the Delta(5)-7-oxo derivative, which was converted into an enone-aldehyde by treatment with Collins' reagent. The conjugated alkene was reduced stereoselectively with SmI2, which, however, did not promote pinacol coupling of the resulting 1,5-keto aldehyde. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00302-1
• 作为产物：
  描述：

  methyl 13-acetyl-14-(2-triethoxysilylethyl)-12-(((1,1-dimethylethyl)dimethylsilyl)oxy)podocarpa-8,11,13-trien-19-oate 在 dimethyl sulfide borane 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到(1S,4aS,13aR)-6-(tert-Butyl-dimethyl-silanyloxy)-9,9-diethoxy-1,4a,7-trimethyl-1,2,3,4,4a,7,9,10,11,12,13,13a-dodecahydro-8-oxa-9-sila-cyclohepta[a]phenanthrene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Functionalisation of Alkylalkoxysilanes. Studies Towards Annulations of Diterpenoids

  摘要：

  Ortho-(2-triethoxysilylethyl) derivatives of aryl ketones undergo oxidative desilylation with H2O2. Tetralone derivatives have served as model substrates for 14-2-(triethoxysilylethyl)-7-oxopodocarpanes, which have been converted into 2-arylethanols in a four-step sequence (BH3. BMS, H2O2, Et3SiH/CF3COOH, TBAF) without isolation of intermediate products (oxasilepin, diol, trifluoroacetate). Use of the 14-(2-diethoxysilylmethyl) analogue improved the overall yield significantly (75 versus 40%). Re-oxidation of ring B with CAN gave the Delta(5)-7-oxo derivative, which was converted into an enone-aldehyde by treatment with Collins' reagent. The conjugated alkene was reduced stereoselectively with SmI2, which, however, did not promote pinacol coupling of the resulting 1,5-keto aldehyde. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00302-1