(3R,E)-1-((4'R,5'S)-2',2'-dimethyl-5'-((4''R,5''S)-2'',2'',5''-trimethyl-1'',3''-dioxolan-4''-yl)-1',3'-dioxolan-4'-yl)hexa-1,5-dien-3-ol | 849775-45-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,E)-1-((4'R,5'S)-2',2'-dimethyl-5'-((4''R,5''S)-2'',2'',5''-trimethyl-1'',3''-dioxolan-4''-yl)-1',3'-dioxolan-4'-yl)hexa-1,5-dien-3-ol
• 英文别名: (3R,E)-1-((4R,5S)-2,2-dimethyl-5-((4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-1,3-dioxolan-4-yl)hexa-1,5-dien-3-ol；(1E,3R)-1-[(4R,5S)-2,2-dimethyl-5-[(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]-1,3-dioxolan-4-yl]hexa-1,5-dien-3-ol
• CAS: 849775-45-7
• 化学式: C₁₇H₂₈O₅
• 分子量: 312.406
• InChiKey: AHWORFVTZZBTEX-VIBMJMMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  (3R,E)-1-((4'R,5'S)-2',2'-dimethyl-5'-((4''R,5''S)-2'',2'',5''-trimethyl-1'',3''-dioxolan-4''-yl)-1',3'-dioxolan-4'-yl)hexa-1,5-dien-3-ol 在 Grubbs catalyst first generation 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.33h， 生成 10-epi-anamarine
  参考文献：
  名称：

  Enantioselective Synthesis of 10-epi-Anamarine via an Iterative Dihydroxylation Sequence

  摘要：

  The enantioselective syntheses of 10-epi-anamarine and 5,10-epi,epi-anamarine have been achieved in 13 to 14 steps. The route relies upon an enantio- and regioselective Sharpless dihydroxylation of either dienoates or trienoates to establish the C-8 to C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route also relies upon a ring-closing metathesis to establish the alpha,beta-unsaturated lactones.

  DOI：

  10.1021/ol047322i
• 作为产物：
  描述：

  (E)-3-((4'R,5'S)-2',2'-dimethyl-5'-((4''R,5''S)-2'',2'',5''-trimethyl-1'',3''-dioxolan-4''-yl)-1',3'-dioxolan-4'-yl)acrylaldehyde 、 (3aS,7aS)-1,3-bis[(4-bromophenyl)methyl]-2-chlorooctahydro-2-(2-propenyl)-1H-1,3,2-benzodiazasilole 以 二氯甲烷 为溶剂， 反应 36.0h， 以92%的产率得到(3R,E)-1-((4'R,5'S)-2',2'-dimethyl-5'-((4''R,5''S)-2'',2'',5''-trimethyl-1'',3''-dioxolan-4''-yl)-1',3'-dioxolan-4'-yl)hexa-1,5-dien-3-ol
  参考文献：
  名称：

  Enantioselective Synthesis of 10-epi-Anamarine via an Iterative Dihydroxylation Sequence

  摘要：

  The enantioselective syntheses of 10-epi-anamarine and 5,10-epi,epi-anamarine have been achieved in 13 to 14 steps. The route relies upon an enantio- and regioselective Sharpless dihydroxylation of either dienoates or trienoates to establish the C-8 to C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route also relies upon a ring-closing metathesis to establish the alpha,beta-unsaturated lactones.

  DOI：

  10.1021/ol047322i

文献信息

• De Novo Asymmetric Synthesis of Anamarine and Its Analogues
  作者：Dong Gao、George A. O'Doherty

  DOI：10.1021/jo051681p

  日期：2005.11.1

  The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.
• Enantioselective Synthesis of 10-<i>e</i><i>pi</i>-Anamarine via an Iterative Dihydroxylation Sequence
  作者：Dong Gao、George A. O'Doherty

  DOI：10.1021/ol047322i

  日期：2005.3.1

  The enantioselective syntheses of 10-epi-anamarine and 5,10-epi,epi-anamarine have been achieved in 13 to 14 steps. The route relies upon an enantio- and regioselective Sharpless dihydroxylation of either dienoates or trienoates to establish the C-8 to C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route also relies upon a ring-closing metathesis to establish the alpha,beta-unsaturated lactones.