methyl (4R,5R,1'S)-5-<1'-(benzyloxy)ethyl>-2-(p-methoxyphenyl)-2-oxazoline-4-carboxylate | 158719-56-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (4R,5R,1'S)-5-<1'-(benzyloxy)ethyl>-2-(p-methoxyphenyl)-2-oxazoline-4-carboxylate
• 英文别名: methyl (4R,5R)-2-(4-methoxyphenyl)-5-[(1S)-1-phenylmethoxyethyl]-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 158719-56-3
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: MFGGNRGZSYLHOQ-KYNGSXCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (4R,5R,1'S)-5-<1'-(benzyloxy)ethyl>-2-(p-methoxyphenyl)-2-oxazoline-4-carboxylate 在 钯 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 24.0h， 以35%的产率得到methyl (4R,5R,1'S)-5-<1'-(hydroxy)ethyl>-2-(p-methoxyphenyl)-2-oxazoline-4-carboxylate
  参考文献：
  名称：

  Highly Diastereoselective Synthesis of 2-Oxazoline-4-carboxylates by Formal [3 + 2] Cycloadditions of a 5-Alkoxyoxazole with .alpha.-Alkoxy Aldehydes Catalyzed by Tin(IV) Chloride

  摘要：

  The formal [3 + 2] cycloaddition of 5-methoxy-2-(p-methoxyphenyl) oxazole with 2(S)-(benzyloxy)propanal and 2(S)-[(tert-butyldimethylsilyl)oxy]propanal in the presence of tin(IV) chloride gave cis-(4R,5S,1'S)- and trans-(4S,5S,1'S)-5-(1'-alkoxyethyl)-4-(methoxycarbonyl)-2-(p-methoxyphenyl)-2-oxazolines with high diastereoselectivity (94 and 92% selectivity, respectively). A similar reaction of 5-methoxy-2-(p-methoxyphenyl) oxazole with 2,3-di-O-benzyl-D-glyceraldehyde gave methyl cis-(4S,5R,1'R)-2-(p-methoxyphenyl)-5-[1',2'-bis(benzyloxy)ethyl]-2-oxazoline-4-carboxylate with high diastereoselectivity (>95% selectivity), and the latter was easily converted to biologically important chiral 2-amino-1,3,4,5-tetrol derivatives.

  DOI：

  10.1021/jo00091a023
• 作为产物：
  描述：

  2-(p-methoxyphenyl)-5-methoxyoxazole 在 四氯化锡 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 29.0h， 生成 methyl (4R,5R,1'S)-5-<1'-(benzyloxy)ethyl>-2-(p-methoxyphenyl)-2-oxazoline-4-carboxylate
  参考文献：
  名称：

  Highly Diastereoselective Synthesis of 2-Oxazoline-4-carboxylates by Formal [3 + 2] Cycloadditions of a 5-Alkoxyoxazole with .alpha.-Alkoxy Aldehydes Catalyzed by Tin(IV) Chloride

  摘要：

  The formal [3 + 2] cycloaddition of 5-methoxy-2-(p-methoxyphenyl) oxazole with 2(S)-(benzyloxy)propanal and 2(S)-[(tert-butyldimethylsilyl)oxy]propanal in the presence of tin(IV) chloride gave cis-(4R,5S,1'S)- and trans-(4S,5S,1'S)-5-(1'-alkoxyethyl)-4-(methoxycarbonyl)-2-(p-methoxyphenyl)-2-oxazolines with high diastereoselectivity (94 and 92% selectivity, respectively). A similar reaction of 5-methoxy-2-(p-methoxyphenyl) oxazole with 2,3-di-O-benzyl-D-glyceraldehyde gave methyl cis-(4S,5R,1'R)-2-(p-methoxyphenyl)-5-[1',2'-bis(benzyloxy)ethyl]-2-oxazoline-4-carboxylate with high diastereoselectivity (>95% selectivity), and the latter was easily converted to biologically important chiral 2-amino-1,3,4,5-tetrol derivatives.

  DOI：

  10.1021/jo00091a023

文献信息

• Highly Diastereoselective Synthesis of 2-Oxazoline-4-carboxylates by Formal [3 + 2] Cycloadditions of a 5-Alkoxyoxazole with .alpha.-Alkoxy Aldehydes Catalyzed by Tin(IV) Chloride
  作者：Hiroyuki Suga、Hiroki Fujieda、Yoshihiro Hirotsu、Toshikazu Ibata

  DOI：10.1021/jo00091a023

  日期：1994.6

  The formal [3 + 2] cycloaddition of 5-methoxy-2-(p-methoxyphenyl) oxazole with 2(S)-(benzyloxy)propanal and 2(S)-[(tert-butyldimethylsilyl)oxy]propanal in the presence of tin(IV) chloride gave cis-(4R,5S,1'S)- and trans-(4S,5S,1'S)-5-(1'-alkoxyethyl)-4-(methoxycarbonyl)-2-(p-methoxyphenyl)-2-oxazolines with high diastereoselectivity (94 and 92% selectivity, respectively). A similar reaction of 5-methoxy-2-(p-methoxyphenyl) oxazole with 2,3-di-O-benzyl-D-glyceraldehyde gave methyl cis-(4S,5R,1'R)-2-(p-methoxyphenyl)-5-[1',2'-bis(benzyloxy)ethyl]-2-oxazoline-4-carboxylate with high diastereoselectivity (>95% selectivity), and the latter was easily converted to biologically important chiral 2-amino-1,3,4,5-tetrol derivatives.