N-[(3S,5R,6S)-5-(benzyloxy)-6-methyl-4-oxo-1-(phenylsulfonyl)piperidinyl]-N-methylbenzamide | 436844-03-0

• 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: N-[(3S,5R,6S)-5-(benzyloxy)-6-methyl-4-oxo-1-(phenylsulfonyl)piperidinyl]-N-methylbenzamide
• 英文别名: N-[(3S,5R,6S)-1-(benzenesulfonyl)-6-methyl-4-oxo-5-phenylmethoxypiperidin-3-yl]-N-methylbenzamide
• CAS: 436844-03-0
• 化学式: C₂₇H₂₈N₂O₅S
• 分子量: 492.596
• InChiKey: ZNDGIPZGBHEIMT-OCDQVXHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(3S,5R,6S)-5-(benzyloxy)-6-methyl-4-oxo-1-(phenylsulfonyl)piperidinyl]-N-methylbenzamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以70%的产率得到N-[(3S,4S,5R,6S)-5-(benzyloxy)-4-hydroxy-6-methyl-1-(phenylsulfonyl)piperidinyl]-N-methylbenzamide
  参考文献：
  名称：

  New Strategy for the Synthesis of Iminoglycitols from Amino Acids

  摘要：

  A novel strategy for the enantioselective synthesis of polyhydroxypiperidines, which can be considered as iminoglycitols or 2,6-dideoxyazasugars, was developed, alpha-Benzolsulfonylamino esters served as a C2N building block while 2-bromo-3-(bromomethyl)oxazoles and -thiazoles contributed a C3-unit to the final piperidine ring. At first a dihydropyridine ring was established via alkylation and bromine-lithium exchange. The keto group of the resulting 5,6-dihydro[1,3]oxazolo- and 5,6-dihydro[1,3]thiazolo[4,5-c]pyridin-7(4H)-ones was reduced and, after alkylation reactions, the azole ring was cleaved, thus providing heteroatom substituents for the target piperdines. Protected 5-amino-3,4-dihydroxy and 5-amino-3-hydroxy-4-thiohydroxypiperdines were obtained in the talose series while Mitsunobu reaction of the intermiediates provided access to the altrose series.

  DOI：

  10.1021/jo010665z
• 作为产物：
  描述：

  5-bromo-4-(bromomethyl)-2-phenyl-1,3-oxazole 在 氢氧化钾 、 sodium tetrahydroborate 、 正丁基锂 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 N-[(3S,5R,6S)-5-(benzyloxy)-6-methyl-4-oxo-1-(phenylsulfonyl)piperidinyl]-N-methylbenzamide
  参考文献：
  名称：

  New Strategy for the Synthesis of Iminoglycitols from Amino Acids

  摘要：

  A novel strategy for the enantioselective synthesis of polyhydroxypiperidines, which can be considered as iminoglycitols or 2,6-dideoxyazasugars, was developed, alpha-Benzolsulfonylamino esters served as a C2N building block while 2-bromo-3-(bromomethyl)oxazoles and -thiazoles contributed a C3-unit to the final piperidine ring. At first a dihydropyridine ring was established via alkylation and bromine-lithium exchange. The keto group of the resulting 5,6-dihydro[1,3]oxazolo- and 5,6-dihydro[1,3]thiazolo[4,5-c]pyridin-7(4H)-ones was reduced and, after alkylation reactions, the azole ring was cleaved, thus providing heteroatom substituents for the target piperdines. Protected 5-amino-3,4-dihydroxy and 5-amino-3-hydroxy-4-thiohydroxypiperdines were obtained in the talose series while Mitsunobu reaction of the intermiediates provided access to the altrose series.

  DOI：

  10.1021/jo010665z