ethyl (4S,6R,7S)-7-benzyloxy-6-(benzyloxymethyl)-4-methoxy-2,4,6,7-tetrahydropyrano[3,4-c]pyrrole-3-carboxylate | 1096364-63-4

• 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: ethyl (4S,6R,7S)-7-benzyloxy-6-(benzyloxymethyl)-4-methoxy-2,4,6,7-tetrahydropyrano[3,4-c]pyrrole-3-carboxylate
• 英文别名: ethyl (4S,6R,7S)-4-methoxy-7-phenylmethoxy-6-(phenylmethoxymethyl)-2,4,6,7-tetrahydropyrano[3,4-c]pyrrole-3-carboxylate
• CAS: 1096364-63-4
• 化学式: C₂₆H₂₉NO₆
• 分子量: 451.519
• InChiKey: DRJQXZAVYLZUDD-DSBYRVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 2,3-dideoxy-3-C-(p-tolylsulfonyl)-4,6-di-O-(phenylmethyl)-α-D-erythro-hex-2-enopyranoside 、 异氰基乙酸乙酯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以81%的产率得到ethyl (4S,6R,7S)-7-benzyloxy-6-(benzyloxymethyl)-4-methoxy-2,4,6,7-tetrahydropyrano[3,4-c]pyrrole-3-carboxylate
  参考文献：
  名称：

  Densely Functionalized Chiral Pyrroles from Endocyclic, Exocyclic, and Acyclic Vinyl Sulfone-Modified Carbohydrates

  摘要：

  A wide range of vinyl sulfone-modified carbohydrates have been prepared as starting materials for the synthesis of polysubstituted chiral pyrroles. All these vinyl sulfones reacted efficiently with ethylisocyanoacetate to generate a plethora of new pyrrole derivatives. Furanosyl rings opened up during pyrrole synthesis, and pyranosyl rings were opened up by reacting the pyrrole with POCl3/DMF. This paper also reports one of the most efficient and practical routes for the synthesis of beta-substituted pyrroles.

  DOI：

  10.1021/jo801948m