(Z)-Methyl (2S)-2-(benzoyloxy)-5-oxopentanoate O-(3,5-bis(tosyloxy)phenyl)oxime

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-Methyl (2S)-2-(benzoyloxy)-5-oxopentanoate O-(3,5-bis(tosyloxy)phenyl)oxime
• 英文别名: [(2S,5Z)-5-[3,5-bis-(4-methylphenyl)sulfonyloxyphenoxy]imino-1-methoxy-1-oxopentan-2-yl] benzoate
• 化学式: C₃₃H₃₁NO₁₁S₂
• 分子量: 681.741
• InChiKey: FUFCCCYDMHGPMV-VMKKIOGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  178
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  α-Methyl 2-(benzoyloxy)glutaric acid 在 硼烷四氢呋喃络合物 、 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (Z)-Methyl (2S)-2-(benzoyloxy)-5-oxopentanoate O-(3,5-bis(tosyloxy)phenyl)oxime
  参考文献：
  名称：

  Synthesis of the Enantiomeric Furobenzofurans, Late Precursors for the Synthesis of (+)- and (-)-Aflatoxins B1, B2, G1, and G2

  摘要：

  Enantiomeric tetrahydrofuro[2,3-b]benzofurans, representing the ABC tricyclic portion of aflatoxins B-1, B-2, G(1), and G(2), were generated from the oxaza-Cope rearrangement of a suitably functionalized O-aryloxime. The O-aryloxime was, in turn, made from the condensation of an enantiomerically pure aldehyde derived from glutamic acid and a substituted phenoxyamine. High regioselectivity with respect to the A-ring substituents of the ABC tricycle was achieved through the use of electrochemistry. The regioselective electrochemical cleavage of 4,6-bis(tosyloxy)-2-(methoxycarbonyl)-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran (22) resulted in a 97/3 mixture of regioisomeric phenols. The regiochemical assignments of the resulting phenols were determined by 2D NOESY NMR. The enantiomeric ratio of the final product was determined to be 96/4 by NMR analysis of diastereomers resulting from the coupling of 31a to (+)- and (+/-)-phenethylamine.

  DOI：

  10.1021/jo00093a008

文献信息

• Synthesis of the Enantiomeric Furobenzofurans, Late Precursors for the Synthesis of (+)- and (-)-Aflatoxins B1, B2, G1, and G2
  作者：Edgar R. Civitello、Henry Rapoport

  DOI：10.1021/jo00093a008

  日期：1994.7

  Enantiomeric tetrahydrofuro[2,3-b]benzofurans, representing the ABC tricyclic portion of aflatoxins B-1, B-2, G(1), and G(2), were generated from the oxaza-Cope rearrangement of a suitably functionalized O-aryloxime. The O-aryloxime was, in turn, made from the condensation of an enantiomerically pure aldehyde derived from glutamic acid and a substituted phenoxyamine. High regioselectivity with respect to the A-ring substituents of the ABC tricycle was achieved through the use of electrochemistry. The regioselective electrochemical cleavage of 4,6-bis(tosyloxy)-2-(methoxycarbonyl)-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran (22) resulted in a 97/3 mixture of regioisomeric phenols. The regiochemical assignments of the resulting phenols were determined by 2D NOESY NMR. The enantiomeric ratio of the final product was determined to be 96/4 by NMR analysis of diastereomers resulting from the coupling of 31a to (+)- and (+/-)-phenethylamine.