4-{6-[3-(tert-Butyldiphenylsilanyloxy)-2-methylpropenyl]-5-methyl-4-triethylsilanyloxytetrahydropyran-2-yl}-but-2-enal | 877833-52-8

• 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: 4-{6-[3-(tert-Butyldiphenylsilanyloxy)-2-methylpropenyl]-5-methyl-4-triethylsilanyloxytetrahydropyran-2-yl}-but-2-enal
• 英文别名: (E)-4-[(2S,4S,5S,6R)-6-[(Z)-3-[tert-butyl(diphenyl)silyl]oxy-2-methylprop-1-enyl]-5-methyl-4-triethylsilyloxyoxan-2-yl]but-2-enal
• CAS: 877833-52-8
• 化学式: C₃₆H₅₄O₄Si₂
• 分子量: 606.993
• InChiKey: HPVXHLFVOBVRQK-GSSRGVRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-{6-[3-(tert-Butyldiphenylsilanyloxy)-2-methylpropenyl]-5-methyl-4-triethylsilanyloxytetrahydropyran-2-yl}-but-2-enal 、 乙氧甲酰基亚甲基三苯基膦 以 四氢呋喃 为溶剂， 反应 4.0h， 以82%的产率得到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：

  (4S,5R,6R)-2-Allyl-6-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-tetrahydro-pyran-2,4-diol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 4-{6-[3-(tert-Butyldiphenylsilanyloxy)-2-methylpropenyl]-5-methyl-4-triethylsilanyloxytetrahydropyran-2-yl}-but-2-enal
  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