(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 | 849775-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• 英文别名: (E)-3-((4R,5S)-2,2-dimethyl-5-((4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-1,3-dioxolan-4-yl)acrylaldehyde；(E)-3-[(4R,5S)-2,2-dimethyl-5-[(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]-1,3-dioxolan-4-yl]prop-2-enal
• CAS: 849775-40-2
• 化学式: C₁₄H₂₂O₅
• 分子量: 270.326
• InChiKey: WDNQJGWLALTRML-VIKGERBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 (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-yl acrylate
  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)prop-2-en-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到(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
  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.