(+)-[(5R,6S,Ss)-6-benzyloxycarbonylamino-6-(methoxycarbonyl)-5-(p-tolylsulfinylamino)]hexyl p-tolylsulfonate | 675125-01-6

• 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: (+)-[(5R,6S,Ss)-6-benzyloxycarbonylamino-6-(methoxycarbonyl)-5-(p-tolylsulfinylamino)]hexyl p-tolylsulfonate
• CAS: 675125-01-6
• 化学式: C₃₀H₃₆N₂O₈S₂
• 分子量: 616.756
• InChiKey: FEJISSKOVXGFER-TUGDBRDXSA-N

反应信息

• 作为反应物：
  描述：

  (+)-[(5R,6S,Ss)-6-benzyloxycarbonylamino-6-(methoxycarbonyl)-5-(p-tolylsulfinylamino)]hexyl p-tolylsulfonate 在 磷酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 28.0h， 以98%的产率得到(-)-methyl (2S)-[2-benzyloxycarbonylamino-2-piperidin-(2'R)-yl]acetate
  参考文献：
  名称：

  Fine-Tuned Aminal Cleavage:  A Concise Route to Differentially Protected Enantiopure syn-α,β-Diamino Esters

  摘要：

  A survey of routes for aminal cleavage of N-sulfinylimidazolidines has been carried out, and selective conditions to cleave the aminal moiety while preserving the sulfinamide group unaltered have been found. Thus, the treatment of enantiopure N-sulfinylimidazolidines with aqueous H3PO4 in THF affords enantiopure N-sulfinyldiamino esters in excellent yields, while the presence of MeOH as cosolvent allows for the simultaneous removal of the sulfinamide group and aminal cleavage. The behavior of these substrates in a variety of chemical transformations has been explored.

  DOI：

  10.1021/jo035613j
• 作为产物：
  描述：

  (+)-methyl [(2S,4R,5S,Ss)-2-phenyl-1-(p-tolylsulfinyl)-5-[4-(toluenesulfonyloxy)butyl]-1,3-imidazolidin-4-yl]carboxylate 在 sodium hydroxide 、 磷酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 8.5h， 生成 (+)-[(5R,6S,Ss)-6-benzyloxycarbonylamino-6-(methoxycarbonyl)-5-(p-tolylsulfinylamino)]hexyl p-tolylsulfonate
  参考文献：
  名称：

  Fine-Tuned Aminal Cleavage:  A Concise Route to Differentially Protected Enantiopure syn-α,β-Diamino Esters

  摘要：

  A survey of routes for aminal cleavage of N-sulfinylimidazolidines has been carried out, and selective conditions to cleave the aminal moiety while preserving the sulfinamide group unaltered have been found. Thus, the treatment of enantiopure N-sulfinylimidazolidines with aqueous H3PO4 in THF affords enantiopure N-sulfinyldiamino esters in excellent yields, while the presence of MeOH as cosolvent allows for the simultaneous removal of the sulfinamide group and aminal cleavage. The behavior of these substrates in a variety of chemical transformations has been explored.

  DOI：

  10.1021/jo035613j