benzyl (6S,7R)-7-methoxy-6-methyl-2-phenyl-6,7-dihydro[1,3]oxazolo[4,5-c]pyridine-5(4H)-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: benzyl (6S,7R)-7-methoxy-6-methyl-2-phenyl-6,7-dihydro[1,3]oxazolo[4,5-c]pyridine-5(4H)-carboxylate
• 英文别名: benzyl (6S,7R)-7-methoxy-6-methyl-2-phenyl-6,7-dihydro-4H-[1,3]oxazolo[4,5-c]pyridine-5-carboxylate
• 化学式: C₂₂H₂₂N₂O₄
• 分子量: 378.428
• InChiKey: YLSLGKZUNXCUSY-HNAYVOBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(6S,7R)-7-methoxy-6-methyl-2-phenyl-5-(phenylsulfonyl)-4,5,6,7-tetrahydro[1,3]oxazolo[4,5-c]pyridine	436843-98-0	C20H20N2O4S	384.456
  ——	(6S)-6-methyl-2-phenyl-5-(phenylsulfonyl)-5,6-dihydro[1,3]oxazolo[4,5-c]pyridin-7(4H)-one	221454-91-7	C19H16N2O4S	368.413
  ——	methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]propanoate	436843-87-7	C20H19BrN2O5S	479.351

反应信息

• 作为产物：
  描述：

  5-bromo-4-(bromomethyl)-2-phenyl-1,3-oxazole 在 N,N-二甲基丙烯基脲 、 sodium tetrahydroborate 、 正丁基锂 、 samarium diiodide 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 乙腈 为溶剂， 反应 35.5h， 生成 benzyl (6S,7R)-7-methoxy-6-methyl-2-phenyl-6,7-dihydro[1,3]oxazolo[4,5-c]pyridine-5(4H)-carboxylate
  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

文献信息

• New Strategy for the Synthesis of Iminoglycitols from Amino Acids
  作者：Sauda Swaleh、Jürgen Liebscher

  DOI：10.1021/jo010665z

  日期：2002.5.1

  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.