(2S,4S,5R,6S)-1-benzyloxy-4,5-dimethoxy-2,6-dimethyl-7-nonyne | 896451-31-3

• 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: (2S,4S,5R,6S)-1-benzyloxy-4,5-dimethoxy-2,6-dimethyl-7-nonyne
• 英文别名: [(2S,4S,5R,6S)-4,5-dimethoxy-2,6-dimethylnon-7-ynoxy]methylbenzene
• CAS: 896451-31-3
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: VAQHDQIMIYIONL-QGZVKYPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6S)-1-benzyloxy-4,5-dimethoxy-2,6-dimethyl-7-nonyne 在 三异丙氧基氯化钛 、 Cyclopentylmagnesium chloride 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 (E)-(4S,5R,6S,8S)-9-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,6-dimethoxy-2,4,8-trimethyl-non-2-en-1-one
  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 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以98%的产率得到(2S,4S,5R,6S)-1-benzyloxy-4,5-dimethoxy-2,6-dimethyl-7-nonyne
  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

• Total Synthesis of Macbecin I
  作者：Justin K. Belardi、Glenn C. Micalizio

  DOI：10.1002/anie.200800400

  日期：2008.5.13
• 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.