(E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid | 791131-46-9

• 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: (E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid
• 英文别名: (E)-3-[(4R,5R)-5-[2-[(4-methoxyphenyl)methoxy]ethyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]but-2-enoic acid
• CAS: 791131-46-9
• 化学式: C₂₀H₂₈O₆
• 分子量: 364.439
• InChiKey: NLCPLKXSHIWHAO-WPWIZFRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid 在 4-二甲氨基吡啶 、 臭氧 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid (S)-4-methyl-2,5-dioxo-hexyl ester
  参考文献：
  名称：

  Syntheses of the C(1−6) and C(19−24) Fragments of Lituarines A, B, and C

  摘要：

  Lituarines A-C are marine natural products comprising a tricyclic spiroacetal bridged at C(8) and C(18) by a functionalized ester linkage conceptually obtained from a C(19-24) alcohol and a C(1-6) carboxylic acid whose oxidation level varies at C(4) and C(5). Stereoselective routes are described to compounds 26 and 27, fully functionalized ester fragments of lituarine A and lituarines B and C, respectively.

  DOI：

  10.1021/ol048396x
• 作为产物：
  描述：

  3-[(4-甲氧基苯基)甲氧基]丙醛 在 sodium hydroxide 、 正丁基锂 、 甲基磺酰胺 、 AD-mix-β 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 水 、 叔丁醇 为溶剂， 反应 116.0h， 生成 (E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid
  参考文献：
  名称：

  Syntheses of the C(1−6) and C(19−24) Fragments of Lituarines A, B, and C

  摘要：

  Lituarines A-C are marine natural products comprising a tricyclic spiroacetal bridged at C(8) and C(18) by a functionalized ester linkage conceptually obtained from a C(19-24) alcohol and a C(1-6) carboxylic acid whose oxidation level varies at C(4) and C(5). Stereoselective routes are described to compounds 26 and 27, fully functionalized ester fragments of lituarine A and lituarines B and C, respectively.

  DOI：

  10.1021/ol048396x

文献信息

• Progress in the Synthesis of the Lituarines:  Stereocontrol in Sequential C−C Bond Formation on a Spirobutenolide Template
  作者：Jeremy Robertson、Jonathan W. P. Dallimore

  DOI：10.1021/ol0520018

  日期：2005.10.1

  [GRAPHICS]We describe elaboration of a tricyclic spirobutenolide corresponding to the C(7-18) tricyclic substructure common to lituarines A-C. Conjugate addition, to install the C(16) methyl, is followed by construction of the crucial C(18-19) bond by silyl enol ether addition to the derived spiroacetal C(18)-O oxonium ion. Esterification with a C(1-6) acid, and selective ozonolysis to release the C(23) carbonyl, complete the assembly of all the carbons present in the lituarine macrocyclic core.
• Syntheses of the C(1−6) and C(19−24) Fragments of Lituarines A, B, and C
  作者：Jeremy Robertson、Jonathan W. P. Dallimore、Paul Meo

  DOI：10.1021/ol048396x

  日期：2004.10.1

  Lituarines A-C are marine natural products comprising a tricyclic spiroacetal bridged at C(8) and C(18) by a functionalized ester linkage conceptually obtained from a C(19-24) alcohol and a C(1-6) carboxylic acid whose oxidation level varies at C(4) and C(5). Stereoselective routes are described to compounds 26 and 27, fully functionalized ester fragments of lituarine A and lituarines B and C, respectively.