N-[(3S,5R,6S)-5-(benzyloxy)-6-(hydroxymethyl)-4-oxo-1-(phenylsulfonyl)piperidinyl]-N-methylbenzamide | 436844-07-4

• 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-(hydroxymethyl)-4-oxo-1-(phenylsulfonyl)piperidinyl]-N-methylbenzamide
• 英文别名: N-[(3S,5R,6S)-1-(benzenesulfonyl)-6-(hydroxymethyl)-4-oxo-5-phenylmethoxypiperidin-3-yl]-N-methylbenzamide
• CAS: 436844-07-4
• 化学式: C₂₇H₂₈N₂O₆S
• 分子量: 508.595
• InChiKey: ALVRMOISDKMCOY-KYPHJKQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(3S,5R,6S)-5-(benzyloxy)-6-(hydroxymethyl)-4-oxo-1-(phenylsulfonyl)piperidinyl]-N-methylbenzamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以51%的产率得到N-[(3S,4S,5R,6S)-5-(benzyloxy)-4-hydroxy-6-(hydroxymethyl)-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：

  (6S,7R)-7-(benzyloxy)-6-(hydroxymethyl)-3-methyl-2-phenyl-5-(phenylsulfonyl)-4,5,6,7-tetrahydro[1,3]oxazolo[4,5-c]pyridine-3-ium methyl sulfate 在 氢氧化钾 作用下， 以46%的产率得到N-[(3S,5R,6S)-5-(benzyloxy)-6-(hydroxymethyl)-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