(4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienal | 1428860-02-9

• 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: (4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienal
• 英文别名: (4R,5E,7S,8S)-4-ethyl-10-methyl-7,8-bis(phenylmethoxy)undeca-5,9-dienal
• CAS: 1428860-02-9
• 化学式: C₂₈H₃₆O₃
• 分子量: 420.592
• InChiKey: HBBRFRTXHGDEAM-KBTMMGLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienal 在 吡啶 、 正丁基锂 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.66h， 生成 tert-butyl (5-((4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienoyl)-1,4,6-trimethoxy-7-methylnaphthalen-2-yl)carbamate
  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：

  (3R,6S,7S,E)-ethyl 6,7-bis(benzyloxy)-3-ethyl-9-methyldeca-4,8-dienoate 在 咪唑 、 sodium cyanide 、 lithium aluminium tetrahydride 、 碘 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienal
  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.