6-Allyl-2-[3-(tert-Butyldiphenylsilanyloxy)-2-methylpropenyl]-3-methyl-4-triethylsilanyloxytetrahydropyran | 877833-51-7

• 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: 6-Allyl-2-[3-(tert-Butyldiphenylsilanyloxy)-2-methylpropenyl]-3-methyl-4-triethylsilanyloxytetrahydropyran
• 英文别名: tert-butyl-[(Z)-2-methyl-3-[(2R,3S,4S,6S)-3-methyl-6-prop-2-enyl-4-triethylsilyloxyoxan-2-yl]prop-2-enoxy]-diphenylsilane
• CAS: 877833-51-7
• 化学式: C₃₅H₅₄O₃Si₂
• 分子量: 578.983
• InChiKey: FPIBNTNUHQLEOA-ILXKHOHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.27
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Allyl-2-[3-(tert-Butyldiphenylsilanyloxy)-2-methylpropenyl]-3-methyl-4-triethylsilanyloxytetrahydropyran 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 6-{6-[3-(tert-Butyldiphenylsilanyloxy)-2-methylpropenyl]-5-methyl-4-triethylsilanyloxytetrahydropyran-2-yl}-hexa-2,4-dienoicacidethylester
  参考文献：
  名称：

  An efficient synthesis of the C1–C14 subunit of (−)-lasonolide A via a target oriented β-C-glycoside formation sequence

  摘要：

  An efficient synthesis of the C-1-C-14 Subunit resident in (-)-lasonolide A is reported herein. The key reaction features that were utilized include a Molander-Reformatsky SmI2 mediated intramolecular aldol reaction followed by a diastereoselective target oriented beta-C-glycoside formation sequence. Lastly, a chemo- and diastereoselective cross-metathesis of a terminal olefin in the presence of a trisubstituted alkene with acrolein and subsequent olefination of the aldehyde moiety allowed for the completion of the (E,E)-diene side chain. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.11.156
• 作为产物：
  描述：

  Bromoaceticacid4-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(1-methyl-2-oxoethyl)-but-2-enylester 在 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 6-Allyl-2-[3-(tert-Butyldiphenylsilanyloxy)-2-methylpropenyl]-3-methyl-4-triethylsilanyloxytetrahydropyran
  参考文献：
  名称：

  An efficient synthesis of the C1–C14 subunit of (−)-lasonolide A via a target oriented β-C-glycoside formation sequence

  摘要：

  An efficient synthesis of the C-1-C-14 Subunit resident in (-)-lasonolide A is reported herein. The key reaction features that were utilized include a Molander-Reformatsky SmI2 mediated intramolecular aldol reaction followed by a diastereoselective target oriented beta-C-glycoside formation sequence. Lastly, a chemo- and diastereoselective cross-metathesis of a terminal olefin in the presence of a trisubstituted alkene with acrolein and subsequent olefination of the aldehyde moiety allowed for the completion of the (E,E)-diene side chain. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.11.156

文献信息

• An efficient synthesis of the C1–C14 subunit of (−)-lasonolide A via a target oriented β-C-glycoside formation sequence
  作者：Kailas B. Sawant、Fei Ding、Michael P. Jennings

  DOI：10.1016/j.tetlet.2005.11.156

  日期：2006.2

  An efficient synthesis of the C-1-C-14 Subunit resident in (-)-lasonolide A is reported herein. The key reaction features that were utilized include a Molander-Reformatsky SmI2 mediated intramolecular aldol reaction followed by a diastereoselective target oriented beta-C-glycoside formation sequence. Lastly, a chemo- and diastereoselective cross-metathesis of a terminal olefin in the presence of a trisubstituted alkene with acrolein and subsequent olefination of the aldehyde moiety allowed for the completion of the (E,E)-diene side chain. (c) 2005 Published by Elsevier Ltd.