(2R)-2-[tert-butyl(diphenyl)silyl]oxy-2-[(1R,2S,4R)-2-ethenyl-4-tri(propan-2-yl)silyloxycyclopentyl]acetaldehyde | 468732-87-8

• 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: (2R)-2-[tert-butyl(diphenyl)silyl]oxy-2-[(1R,2S,4R)-2-ethenyl-4-tri(propan-2-yl)silyloxycyclopentyl]acetaldehyde
• CAS: 468732-87-8
• 化学式: C₃₄H₅₂O₃Si₂
• 分子量: 564.956
• InChiKey: XEWUFAIKANXYHH-GRPYAHQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-hept-6-en-2-yl-2-(diethoxyphosphoryl)acetate 、 (2R)-2-[tert-butyl(diphenyl)silyl]oxy-2-[(1R,2S,4R)-2-ethenyl-4-tri(propan-2-yl)silyloxycyclopentyl]acetaldehyde 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 、 [(E,2S)-7-[(1S,2R,4R)-2-[(1R)-1-[tert-butyl(diphenyl)silyl]oxy-2-oxoethyl]-4-tri(propan-2-yl)silyloxycyclopentyl]hept-6-en-2-yl] 2-diethoxyphosphorylacetate
  参考文献：
  名称：

  Concise Total Synthesis of (+)-Brefeldin A:  A Combined β-Lactone/Cross-Metathesis-Based Strategy

  摘要：

  A highly convergent total synthesis of (+)-brefeldin A that relies on a diastereoselective, beta-lactone-based cyclopentane synthesis combined with complex cross-metathesis reactions is described. The utility of beta-lactones for natural product synthesis and the versatility of cross-metathesis in this context were demonstrated, including the tolerance of an epimerizable aldehyde and a beta-lactone.

  DOI：

  10.1021/ol026438g
• 作为产物：
  描述：

  (R)-3-Triisopropylsilanyloxy-hex-5-enoic acid ethyl ester 在 Grubbs catalyst first generation 草酰氯 、 四氯化钛 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 116.0h， 生成 (2R)-2-[tert-butyl(diphenyl)silyl]oxy-2-[(1R,2S,4R)-2-ethenyl-4-tri(propan-2-yl)silyloxycyclopentyl]acetaldehyde
  参考文献：
  名称：

  Concise Total Synthesis of (+)-Brefeldin A:  A Combined β-Lactone/Cross-Metathesis-Based Strategy

  摘要：

  A highly convergent total synthesis of (+)-brefeldin A that relies on a diastereoselective, beta-lactone-based cyclopentane synthesis combined with complex cross-metathesis reactions is described. The utility of beta-lactones for natural product synthesis and the versatility of cross-metathesis in this context were demonstrated, including the tolerance of an epimerizable aldehyde and a beta-lactone.

  DOI：

  10.1021/ol026438g

文献信息

• Concise Total Synthesis of (+)-Brefeldin A:  A Combined β-Lactone/Cross-Metathesis-Based Strategy
  作者：Yingcai Wang、Daniel Romo

  DOI：10.1021/ol026438g

  日期：2002.9.1

  A highly convergent total synthesis of (+)-brefeldin A that relies on a diastereoselective, beta-lactone-based cyclopentane synthesis combined with complex cross-metathesis reactions is described. The utility of beta-lactones for natural product synthesis and the versatility of cross-metathesis in this context were demonstrated, including the tolerance of an epimerizable aldehyde and a beta-lactone.