4-OBn-cephalosporolide G | 1482494-95-0

• 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: 4-OBn-cephalosporolide G
• 英文别名: (4S,5R,10R)-4-hydroxy-10-methyl-5-phenylmethoxyoxecane-2,7-dione
• CAS: 1482494-95-0
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: JLIBKLWYCVBKLY-UHOFOFEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-OBn-cephalosporolide G 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以69%的产率得到cephalosporolide G
  参考文献：
  名称：

  Cephalosporolide B Serving as a Versatile Synthetic Precursor: Asymmetric Biomimetic Total Syntheses of Cephalosporolides C, E, F, G, and (4-OMe-)G

  摘要：

  Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.

  DOI：

  10.1021/ol402913m
• 作为产物：
  描述：

  (2R,4aS,7S,8aS)-4a,7-dihydroxy-2-methyl-3,4,4a,7,8,8a-hexahydrobenzo-1(2H)-pyran 在 咪唑 、 4-二甲氨基吡啶 、 2-叠氮丙二酸二甲酯 、 Rh₂(OAc)4 、 sodium acetate 、 氟化氢吡啶 、 间氯过氧苯甲酸 、 10-camphorsulfonic acid 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 4-OBn-cephalosporolide G
  参考文献：
  名称：

  Cephalosporolide B Serving as a Versatile Synthetic Precursor: Asymmetric Biomimetic Total Syntheses of Cephalosporolides C, E, F, G, and (4-OMe-)G

  摘要：

  Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.

  DOI：

  10.1021/ol402913m

文献信息

• Cephalosporolide B Serving as a Versatile Synthetic Precursor: Asymmetric Biomimetic Total Syntheses of Cephalosporolides C, E, F, G, and (4-OMe-)G
  作者：Liyan Song、Yuan Liu、Rongbiao Tong

  DOI：10.1021/ol402913m

  日期：2013.11.15

  Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.