(5R,6S,7S,Z)-6,7-bis(benzyloxy)-9-methyldeca-3,8-dien-5-ol | 1428860-17-6

• 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: (5R,6S,7S,Z)-6,7-bis(benzyloxy)-9-methyldeca-3,8-dien-5-ol
• 英文别名: (3Z,5R,6S,7S)-9-methyl-6,7-bis(phenylmethoxy)deca-3,8-dien-5-ol
• CAS: 1428860-17-6
• 化学式: C₂₅H₃₂O₃
• 分子量: 380.527
• InChiKey: QCDFKXNDWXJGKM-NEWXXXIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,6S,7S,Z)-6,7-bis(benzyloxy)-9-methyldeca-3,8-dien-5-ol 在 咪唑 、 sodium cyanide 、 lithium aluminium tetrahydride 、 碘 、 丙酸 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienenitrile
  参考文献：
  名称：

  Studies toward Total Synthesis of Divergolides C and D

  摘要：

  A facile synthesis of the western segment of divergolides C and D has been developed. Exploratory studies with two disconnections, i.e., C4-C5 vs C5-C6, for elaboration of the ansa bridge to the sterically demanding hexasubstituted naphthalenic aromatic core using a chiral synthon assembled from D-glucose via a stereoselective Johnson orthoester rearrangement Is described. The studies set the stage for the completion of the total synthesis of the biologically important novel ansamycins, divergolides C and D, and their structural congeners.

  DOI：

  10.1021/ol400528g
• 作为产物：
  描述：

  、 溴化异丙基(三苯基)磷 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以89%的产率得到(5R,6S,7S,Z)-6,7-bis(benzyloxy)-9-methyldeca-3,8-dien-5-ol
  参考文献：
  名称：

  Studies toward Total Synthesis of Divergolides C and D

  摘要：

  A facile synthesis of the western segment of divergolides C and D has been developed. Exploratory studies with two disconnections, i.e., C4-C5 vs C5-C6, for elaboration of the ansa bridge to the sterically demanding hexasubstituted naphthalenic aromatic core using a chiral synthon assembled from D-glucose via a stereoselective Johnson orthoester rearrangement Is described. The studies set the stage for the completion of the total synthesis of the biologically important novel ansamycins, divergolides C and D, and their structural congeners.

  DOI：

  10.1021/ol400528g

文献信息

• Studies toward Total Synthesis of Divergolides C and D
  作者：Sivappa Rasapalli、Gopalakrishna Jarugumilli、Gangadhara Rao Yarrapothu、James A. Golen、Arnold L. Rheingold

  DOI：10.1021/ol400528g

  日期：2013.4.5

  A facile synthesis of the western segment of divergolides C and D has been developed. Exploratory studies with two disconnections, i.e., C4-C5 vs C5-C6, for elaboration of the ansa bridge to the sterically demanding hexasubstituted naphthalenic aromatic core using a chiral synthon assembled from D-glucose via a stereoselective Johnson orthoester rearrangement Is described. The studies set the stage for the completion of the total synthesis of the biologically important novel ansamycins, divergolides C and D, and their structural congeners.