(1R,2S,4R)-2-((S)-Toluene-4-sulfinyl)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester | 191795-25-2

• 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: (1R,2S,4R)-2-((S)-Toluene-4-sulfinyl)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (1R,2S,4R)-2-[(S)-(4-methylphenyl)sulfinyl]-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 191795-25-2
• 化学式: C₁₈H₂₂O₄S
• 分子量: 334.436
• InChiKey: BKRDINNHRXUMFP-OAOYVAKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R)-2-((S)-Toluene-4-sulfinyl)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester 在 四氧化锇 、 十二/十四烷基二甲基氧化胺 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以94%的产率得到(1R,2S,4R,5S,6R)-5,6-Dihydroxy-2-((S)-toluene-4-sulfinyl)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of (+)-shikimic acid and (+)-5-epi-shikimic acid by asymmetric Diels-Alder reaction of (S)-α-sulfinylacrylates

  摘要：

  Enantiopure (S) benzyl and t-butyl 2-p-tolylsulfinylpropenoates (1 and 2) were readily prepared by Mannich condensation of (R) p-tolylsulfinylacetates (CH2O+Me2NH), followed by in situ nitrogen quaternization. These new chiral dienophiles reacted with furan at high pressures (4-13 Kbar) at rt to afford mainly a 2:1 mixture of both endo adducts (endo-B+endo-A). Enantiopure endo-4B and endo-4A were stereoselectively transformed into (+)-shikimic acid and (+)-5-epi-shikimic acid respectively, by dihydroxylation of the double bond, removal of the sulfinyl group, basic opening of the oxabicyclic skeleton and hydrolysis of the ester moiety. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00151-1
• 作为产物：
  描述：

  (+)-(RS)-(甲苯-4-亚磺酰基)-乙酸叔丁酯 在 calcium carbonate 、 碘甲烷 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 25.0 ℃ 、400.0 MPa 条件下， 反应 131.0h， 生成 (1R,2S,4R)-2-((S)-Toluene-4-sulfinyl)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of (+)-shikimic acid and (+)-5-epi-shikimic acid by asymmetric Diels-Alder reaction of (S)-α-sulfinylacrylates

  摘要：

  Enantiopure (S) benzyl and t-butyl 2-p-tolylsulfinylpropenoates (1 and 2) were readily prepared by Mannich condensation of (R) p-tolylsulfinylacetates (CH2O+Me2NH), followed by in situ nitrogen quaternization. These new chiral dienophiles reacted with furan at high pressures (4-13 Kbar) at rt to afford mainly a 2:1 mixture of both endo adducts (endo-B+endo-A). Enantiopure endo-4B and endo-4A were stereoselectively transformed into (+)-shikimic acid and (+)-5-epi-shikimic acid respectively, by dihydroxylation of the double bond, removal of the sulfinyl group, basic opening of the oxabicyclic skeleton and hydrolysis of the ester moiety. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00151-1