6(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}-vinyl)-5,6-dihydropyran-2-one | 411242-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}-vinyl)-5,6-dihydropyran-2-one
• 英文别名: (2R)-2-[(E)-2-[(4R,5R)-5-[(Z,2R)-4-bromo-2-[tert-butyl(diphenyl)silyl]oxybut-3-enyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethenyl]-2,3-dihydropyran-6-one
• CAS: 411242-16-5
• 化学式: C₃₃H₄₁BrO₅Si
• 分子量: 625.675
• InChiKey: FEIKMLMZGJMCHL-ULAXTYDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}-vinyl)-5,6-dihydropyran-2-one 在 四(三苯基膦)钯 吡啶 、 2,6-二甲基吡啶 、 Montmorillonite K₁₀ 、 双氧水 、 silver(l) oxide 、 三氯化磷 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 为溶剂， 反应 23.17h， 生成 1-[1(R)-(tert-butyldimethylsilanyloxy)-1(R)-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2(R)-yl)allyl]-3(R),10-bis(tert-butyldiphenylsilanyloxy)-deca-4(Z),6(Z),8(E)-trienyl bis[2-(trimethylsilanyl)ethyl] phosphate
  参考文献：
  名称：

  Asymmetric Total Synthesis of (+)-Fostriecin

  摘要：

  [GRAPHICS]The title compound, a potent protein phosphatase inhibitor and anticancer agent, was prepared by an efficient, multiconvergent asymmetric synthesis. Key transformations include a ring forming olefin metathesis leading to the a-p-unsaturated lactone and creation of the triene moiety via Suzuki cross-coupling.

  DOI：

  10.1021/ol025537r
• 作为产物：
  描述：

  5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(S)-trimethyl-[1,3]dioxolane-4(S)-carbaldehyde 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) (+)-Ipc₂BOMe 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 6(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}-vinyl)-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of (+)-Fostriecin

  摘要：

  [GRAPHICS]The title compound, a potent protein phosphatase inhibitor and anticancer agent, was prepared by an efficient, multiconvergent asymmetric synthesis. Key transformations include a ring forming olefin metathesis leading to the a-p-unsaturated lactone and creation of the triene moiety via Suzuki cross-coupling.

  DOI：

  10.1021/ol025537r

文献信息

• Asymmetric Total Synthesis of (+)-Fostriecin
  作者：Y. Krishna Reddy、J. R. Falck

  DOI：10.1021/ol025537r

  日期：2002.3.1

  [GRAPHICS]The title compound, a potent protein phosphatase inhibitor and anticancer agent, was prepared by an efficient, multiconvergent asymmetric synthesis. Key transformations include a ring forming olefin metathesis leading to the a-p-unsaturated lactone and creation of the triene moiety via Suzuki cross-coupling.