(6S,7S)-6-methyl-2-phenyl-5-(phenylsulfonyl)-7-phthalimido-4,5,6,7-tetrahydro[1,3]oxazolo[4,5-c]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (6S,7S)-6-methyl-2-phenyl-5-(phenylsulfonyl)-7-phthalimido-4,5,6,7-tetrahydro[1,3]oxazolo[4,5-c]pyridine
• 英文别名: 2-[(6S,7S)-5-(benzenesulfonyl)-6-methyl-2-phenyl-6,7-dihydro-4H-[1,3]oxazolo[4,5-c]pyridin-7-yl]isoindole-1,3-dione
• 化学式: C₂₇H₂₁N₃O₅S
• 分子量: 499.547
• InChiKey: QBWNWYRWVRBYAP-SBUREZEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-bromo-4-(bromomethyl)-2-phenyl-1,3-oxazole 在 sodium tetrahydroborate 、 正丁基锂 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 乙腈 为溶剂， 反应 4.0h， 生成 (6S,7S)-6-methyl-2-phenyl-5-(phenylsulfonyl)-7-phthalimido-4,5,6,7-tetrahydro[1,3]oxazolo[4,5-c]pyridine
  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.