Benzoic acid (3S,4S,5R)-5-((R)-1-methoxycarbonyl-ethyl)-4-methyl-2-oxo-tetrahydro-furan-3-yl ester

• 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: Benzoic acid (3S,4S,5R)-5-((R)-1-methoxycarbonyl-ethyl)-4-methyl-2-oxo-tetrahydro-furan-3-yl ester
• 英文别名: [(3S,4S,5R)-5-[(2R)-1-methoxy-1-oxopropan-2-yl]-4-methyl-2-oxooxolan-3-yl] benzoate
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: GMVLVSQXPYDBMG-YGNMPJRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6α-hydroxy-5α,7α-dimethylcyclohepta-1,3-diene 在 lead(IV) acetate 、 sodium disulfite 、 四氧化锇 、 水 、 氧气 、 tetraphenylporphyrin 、 三乙胺 、 三苯基膦 、 pyridinium chlorochromate 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 101.0h， 生成 Benzoic acid (3S,4S,5R)-5-((R)-1-methoxycarbonyl-ethyl)-4-methyl-2-oxo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Organoiron-templated stereocontrolled alkylation of enolates: functionalization of cycloheptadienones to give useful synthetic building blocks

  摘要：

  Conversion of eta4-cycloheptatriene-Fe(CO)2P(OPh)3 to ketocycloheptadiene-Fe(CO)2P(OPh)3 complex 7 was accomplished by hydroboration followed by Swern oxidation. Methylation and hydroxylation of the enolate from 7 proceeds with complete stereoselectivity, anti to the metal moiety, and introduction of two methyl or hydroxyl groups at the alpha and alpha' positions was accomplished in high overall yield. Reduction of the ketone group on these complexes occurs with high stereoselectivity and is controlled by the boat conformation adopted by these complexes. The product of these reaction sequences were demetalated to give cycloheptadiene derivatives that were further functionalized to give a C(9)-C(14) subunit of calyculin A1 and a C(19)-C(25) subunit of swinholide A.

  DOI：

  10.1021/jo00057a041

文献信息

• Organoiron-templated stereocontrolled alkylation of enolates: functionalization of cycloheptadienones to give useful synthetic building blocks
  作者：Anthony J. Pearson、Kieyoung Chang

  DOI：10.1021/jo00057a041

  日期：1993.2

  Conversion of eta4-cycloheptatriene-Fe(CO)2P(OPh)3 to ketocycloheptadiene-Fe(CO)2P(OPh)3 complex 7 was accomplished by hydroboration followed by Swern oxidation. Methylation and hydroxylation of the enolate from 7 proceeds with complete stereoselectivity, anti to the metal moiety, and introduction of two methyl or hydroxyl groups at the alpha and alpha' positions was accomplished in high overall yield. Reduction of the ketone group on these complexes occurs with high stereoselectivity and is controlled by the boat conformation adopted by these complexes. The product of these reaction sequences were demetalated to give cycloheptadiene derivatives that were further functionalized to give a C(9)-C(14) subunit of calyculin A1 and a C(19)-C(25) subunit of swinholide A.