(E)-(1S,4S,5R,6S,8S)-9-(benzyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-5,6-dimethoxy-2,4,8-trimethylnon-2-en-1-ol | 896451-28-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(1S,4S,5R,6S,8S)-9-(benzyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-5,6-dimethoxy-2,4,8-trimethylnon-2-en-1-ol
• 英文别名: (E,1S,4S,5R,6S,8S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5,6-dimethoxy-2,4,8-trimethyl-9-phenylmethoxynon-2-en-1-ol
• CAS: 896451-28-8
• 化学式: C₂₆H₄₂O₆
• 分子量: 450.616
• InChiKey: AOAJQRIBXCIXAS-LVUYWWHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-(1S,4S,5R,6S,8S)-9-(benzyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-5,6-dimethoxy-2,4,8-trimethylnon-2-en-1-ol 在 甲醇 、 4-甲基苯磺酸吡啶 作用下， 反应 24.0h， 生成 (E)-(2S,3S,6S,7R,8S,10S)-11-Benzyloxy-7,8-dimethoxy-4,6,10-trimethyl-undec-4-ene-1,2,3-triol
  参考文献：
  名称：

  Studies on the Syntheses of Benzoquinone Ansamycin Antibiotics. Syntheses of the C(5)−C(15) Subunits of Macbecin I, Geldanamycin, and Herbimycin A

  摘要：

  [graphics]A general and convergent route to the C(5)-C(15) subunits of the benzoquinone ansamycin antibiotics macbecin I, geldanamycin, and herbimycin A is described. Each subunit is prepared by the stepwise coupling of differentially functionalized aldehydes with a pentenyl dianion equivalent derived from diastereoselective pentynylation and regioselective reductive coupling.

  DOI：

  10.1021/ol0607995
• 作为产物：
  描述：

  L-甘油醛缩丙酮 在 三异丙氧基氯化钛 、 L-Selectride 、 Cyclopentylmagnesium chloride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.5h， 生成 (E)-(1S,4S,5R,6S,8S)-9-(benzyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-5,6-dimethoxy-2,4,8-trimethylnon-2-en-1-ol
  参考文献：
  名称：

  Studies on the Syntheses of Benzoquinone Ansamycin Antibiotics. Syntheses of the C(5)−C(15) Subunits of Macbecin I, Geldanamycin, and Herbimycin A

  摘要：

  [graphics]A general and convergent route to the C(5)-C(15) subunits of the benzoquinone ansamycin antibiotics macbecin I, geldanamycin, and herbimycin A is described. Each subunit is prepared by the stepwise coupling of differentially functionalized aldehydes with a pentenyl dianion equivalent derived from diastereoselective pentynylation and regioselective reductive coupling.

  DOI：

  10.1021/ol0607995

文献信息

• Studies on the Syntheses of Benzoquinone Ansamycin Antibiotics. Syntheses of the C(5)−C(15) Subunits of Macbecin I, Geldanamycin, and Herbimycin A
  作者：Justin K. Belardi、Glenn C. Micalizio

  DOI：10.1021/ol0607995

  日期：2006.5.1

  [graphics]A general and convergent route to the C(5)-C(15) subunits of the benzoquinone ansamycin antibiotics macbecin I, geldanamycin, and herbimycin A is described. Each subunit is prepared by the stepwise coupling of differentially functionalized aldehydes with a pentenyl dianion equivalent derived from diastereoselective pentynylation and regioselective reductive coupling.