(+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate | 246545-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2R,3S,4R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[dimethyl(phenyl)silyl]-4-[(E,1R)-1-hydroxy-3-[(2R,3R)-3-nonyloxiran-2-yl]prop-2-enyl]-5-oxopyrrolidine-1-carboxylate
• CAS: 246545-53-9
• 化学式: C₃₈H₆₅NO₆Si₂
• 分子量: 688.108
• InChiKey: QGQBDPQLQNPWOK-FOMNLRTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.58
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-tert-butyl (2R,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxy-1-hydroxytetradec-2-enylidene]-5-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  Fleming−Tamao Oxidation and Masked Hydroxyl Functionality:  Total Synthesis of (+)-Pramanicin and Structural Elucidation of the Antifungal Natural Product (−)-Pramanicin

  摘要：

  The total synthesis of (+)-pramanicin (41b) is reported, thereby establishing the relative and absolute stereochemistry of the naturally occurring antifungal agent. The key steps involve (i) conjugate addition of the diethyl((diethylamino)diphenylsilyl)zincate to a suitably protected gamma-lactam 3 and quenching of the resultant enolate with the alpha,beta-unsaturated gamma,delta-epoxy aldehyde 2 (X = H), (ii) Ni(acac)(2)-catalyzed hydroxylation of a beta-dicarbonyl array, and (iii) Fleming-Tamao oxidation to reveal the masked C-3 hydroxyl group.

  DOI：

  10.1021/jo9905672
• 作为产物：
  描述：

  (E)-4,5-epoxytetradec-2-en-1-ol 在 diethylzinc 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  Fleming−Tamao Oxidation and Masked Hydroxyl Functionality:  Total Synthesis of (+)-Pramanicin and Structural Elucidation of the Antifungal Natural Product (−)-Pramanicin

  摘要：

  The total synthesis of (+)-pramanicin (41b) is reported, thereby establishing the relative and absolute stereochemistry of the naturally occurring antifungal agent. The key steps involve (i) conjugate addition of the diethyl((diethylamino)diphenylsilyl)zincate to a suitably protected gamma-lactam 3 and quenching of the resultant enolate with the alpha,beta-unsaturated gamma,delta-epoxy aldehyde 2 (X = H), (ii) Ni(acac)(2)-catalyzed hydroxylation of a beta-dicarbonyl array, and (iii) Fleming-Tamao oxidation to reveal the masked C-3 hydroxyl group.

  DOI：

  10.1021/jo9905672

文献信息

• Fleming−Tamao Oxidation and Masked Hydroxyl Functionality:  Total Synthesis of (+)-Pramanicin and Structural Elucidation of the Antifungal Natural Product (−)-Pramanicin
  作者：Anthony G. M. Barrett、John Head、Marie L. Smith、Nicholas S. Stock、A. J. P. White、D. J. Williams

  DOI：10.1021/jo9905672

  日期：1999.8.1

  The total synthesis of (+)-pramanicin (41b) is reported, thereby establishing the relative and absolute stereochemistry of the naturally occurring antifungal agent. The key steps involve (i) conjugate addition of the diethyl((diethylamino)diphenylsilyl)zincate to a suitably protected gamma-lactam 3 and quenching of the resultant enolate with the alpha,beta-unsaturated gamma,delta-epoxy aldehyde 2 (X = H), (ii) Ni(acac)(2)-catalyzed hydroxylation of a beta-dicarbonyl array, and (iii) Fleming-Tamao oxidation to reveal the masked C-3 hydroxyl group.