(1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-(1-pentenyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester | 805325-71-7

• 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: (1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-(1-pentenyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester
• 英文别名: (4-methoxyphenyl)methyl (1S,2S,6R)-2-[tert-butyl(dimethyl)silyl]oxy-5-oxo-4-[(E)-pent-1-enyl]-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate
• CAS: 805325-71-7
• 化学式: C₂₆H₃₆O₆Si
• 分子量: 472.654
• InChiKey: WWVHMYOLLZJEBL-DJJNJRNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-(1-pentenyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester 在 palladium on activated charcoal 、 二(氰基苯)二氯化钯 sodium tetrahydroborate 、 氢气 、 三氟乙酸 、 对苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 30.33h， 生成 (1aS,2S,5R,7S,7aS)-2-(tert-butyldimethylsiloxy)-7-hydroxy-5-propyl-1a,2,5,6,7,7a-hexahydro-3H-1,4-dioxa-cyclopropa[b]naphthalen-3-one
  参考文献：
  名称：

  Stereoselective Total Synthesis of ent-EI-1941-2 and Epi-ent-EI-1941-2

  摘要：

  The first asymmetric total syntheses of ent-EI-1941-2 and epi-ent-EI-1941-2 have been accomplished, starting from a chiral epoxy iodoquinone 6, a key intermediate in our total syntheses of epoxyquinols A and B. A key step in the preparation of ent-EI-1941-2 is an intramolecular carboxypalladation via a 6-endo cyclization mode, followed by beta-hydride elimination, while carboxymercuration is a key step in the synthesis of epi-ent-EI-1941-2.

  DOI：

  10.1021/ol0481479
• 作为产物：
  描述：

  (4R,6R,7S)-2-iodo-9,9-dimethyl-5,8,10-trioxatricyclo[5.4.0.0^4,6]undec-1-en-3-one 在 二(氰基苯)二氯化钯 2,6-二甲基吡啶 、 manganese(IV) oxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 三苯胂 、 三氟乙酸 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 18.17h， 生成 (1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-(1-pentenyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester
  参考文献：
  名称：

  Stereoselective Total Synthesis of ent-EI-1941-2 and Epi-ent-EI-1941-2

  摘要：

  The first asymmetric total syntheses of ent-EI-1941-2 and epi-ent-EI-1941-2 have been accomplished, starting from a chiral epoxy iodoquinone 6, a key intermediate in our total syntheses of epoxyquinols A and B. A key step in the preparation of ent-EI-1941-2 is an intramolecular carboxypalladation via a 6-endo cyclization mode, followed by beta-hydride elimination, while carboxymercuration is a key step in the synthesis of epi-ent-EI-1941-2.

  DOI：

  10.1021/ol0481479

文献信息

• Stereoselective Total Synthesis of <i>ent</i>-EI-1941-2 and Epi-<i>ent</i>-EI-1941-2
  作者：Mitsuru Shoji、Takao Uno、Yujiro Hayashi

  DOI：10.1021/ol0481479

  日期：2004.11.1

  The first asymmetric total syntheses of ent-EI-1941-2 and epi-ent-EI-1941-2 have been accomplished, starting from a chiral epoxy iodoquinone 6, a key intermediate in our total syntheses of epoxyquinols A and B. A key step in the preparation of ent-EI-1941-2 is an intramolecular carboxypalladation via a 6-endo cyclization mode, followed by beta-hydride elimination, while carboxymercuration is a key step in the synthesis of epi-ent-EI-1941-2.