(E)-(2S,3R,6S,7R,8S,10S)-11-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-7,8-dimethoxy-2,4,6,10-tetramethylundec-4-en-3-ol | 896451-26-6

• 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: (E)-(2S,3R,6S,7R,8S,10S)-11-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-7,8-dimethoxy-2,4,6,10-tetramethylundec-4-en-3-ol
• 英文别名: (E,2S,3R,6S,7R,8S,10S)-1-[tert-butyl(diphenyl)silyl]oxy-7,8-dimethoxy-2,4,6,10-tetramethyl-11-phenylmethoxyundec-4-en-3-ol
• CAS: 896451-26-6
• 化学式: C₄₀H₅₈O₅Si
• 分子量: 646.983
• InChiKey: HGTOMJWEFFRZSJ-IRCHQWSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.42
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(2S,3R,6S,7R,8S,10S)-11-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-7,8-dimethoxy-2,4,6,10-tetramethylundec-4-en-3-ol 在 四丁基氟化铵 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4R,5S)-4-((E)-(4S,5R,6S,8S)-9-(benzyloxy)-5,6-dimethoxy-4,8-dimethylnon-2-en-2-yl)-2,2,5-trimethyl-1,3-dioxane
  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：

  (2S,4S,5R,6S)-1-benzyloxy-4-methoxy-2,6-dimethylnon-7-yn-5-ol 在 三异丙氧基氯化钛 、 sodium hydride 、 Cyclopentylmagnesium chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 7.0h， 生成 (E)-(2S,3R,6S,7R,8S,10S)-11-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-7,8-dimethoxy-2,4,6,10-tetramethylundec-4-en-3-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.