ethyl (S,E)-5-(4,4'-dimethoxytrityloxy)-4-methyl-2-pentenoate | 1352952-87-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: ethyl (S,E)-5-(4,4'-dimethoxytrityloxy)-4-methyl-2-pentenoate
• 英文别名: ethyl (E,4S)-5-[bis(4-methoxyphenyl)-phenylmethoxy]-4-methylpent-2-enoate
• CAS: 1352952-87-4
• 化学式: C₂₉H₃₂O₅
• 分子量: 460.57
• InChiKey: GWEXFJMHRRXZTG-WYWXSHKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  ethyl (S,E)-5-(4,4'-dimethoxytrityloxy)-4-methyl-2-pentenoate 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 copper(I) bromide dimethylsulfide complex 、 L-(+)-酒石酸二异丙酯 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 癸烷 、 正己烷 、 二氯甲烷 、 mineral oil 为溶剂， 反应 24.5h， 生成 (2R,3R,4S)-1-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-(((4-methoxybenzyl)oxy)methyl)-2-methylhex-5-en-3-ol
  参考文献：
  名称：

  Stereoselective synthesis of a fully protected C13–C23 fragment of tedanolide

  摘要：

  The combination of a high-yielding dienyllithium addition and a highly diastereoselective 1,2-reduction allows the preparation of the completely protected C-13-C-23 fragment 3 of the potent cytotoxic agent tedanolide 1. A convergent approach was used, namely a late stage coupling of the dienyllithium 16 with the selectively protected aldehyde 5 followed by oxidation-reduction and final epoxidation to give 3. The dienylstannane 4 was prepared from the dibromide 6 in five steps, the key step being the highly regio-and stereoselective stannylcupration of the alkyne 7. The commercially available hydroxy ester 10 was converted in 11 steps to the aldehyde 5. The compound 3 could potentially be a key intermediate for the synthesis of tedanolide 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.024
• 作为产物：
  描述：

  (R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-methyl-propionic acid methyl ester 在 lithium aluminium tetrahydride 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 生成 ethyl (S,E)-5-(4,4'-dimethoxytrityloxy)-4-methyl-2-pentenoate
  参考文献：
  名称：

  Stereoselective synthesis of a fully protected C13–C23 fragment of tedanolide

  摘要：

  The combination of a high-yielding dienyllithium addition and a highly diastereoselective 1,2-reduction allows the preparation of the completely protected C-13-C-23 fragment 3 of the potent cytotoxic agent tedanolide 1. A convergent approach was used, namely a late stage coupling of the dienyllithium 16 with the selectively protected aldehyde 5 followed by oxidation-reduction and final epoxidation to give 3. The dienylstannane 4 was prepared from the dibromide 6 in five steps, the key step being the highly regio-and stereoselective stannylcupration of the alkyne 7. The commercially available hydroxy ester 10 was converted in 11 steps to the aldehyde 5. The compound 3 could potentially be a key intermediate for the synthesis of tedanolide 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.024

文献信息

• Stereoselective synthesis of a fully protected C13–C23 fragment of tedanolide
  作者：Michael E. Jung、Dongwon Yoo

  DOI：10.1016/j.tet.2011.10.024

  日期：2011.12

  The combination of a high-yielding dienyllithium addition and a highly diastereoselective 1,2-reduction allows the preparation of the completely protected C-13-C-23 fragment 3 of the potent cytotoxic agent tedanolide 1. A convergent approach was used, namely a late stage coupling of the dienyllithium 16 with the selectively protected aldehyde 5 followed by oxidation-reduction and final epoxidation to give 3. The dienylstannane 4 was prepared from the dibromide 6 in five steps, the key step being the highly regio-and stereoselective stannylcupration of the alkyne 7. The commercially available hydroxy ester 10 was converted in 11 steps to the aldehyde 5. The compound 3 could potentially be a key intermediate for the synthesis of tedanolide 1. (C) 2011 Elsevier Ltd. All rights reserved.