N-hydroxy-5-norbornene-2,3-dicarboximide ester of N-benzyloxycarbonyl-DL-2-hydroxy-3-aminopropanoic acid | 66962-64-9

• 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: N-hydroxy-5-norbornene-2,3-dicarboximide ester of N-benzyloxycarbonyl-DL-2-hydroxy-3-aminopropanoic acid
• 英文别名: (3,5-Dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl) 2-hydroxy-3-(phenylmethoxycarbonylamino)propanoate；(3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl) 2-hydroxy-3-(phenylmethoxycarbonylamino)propanoate
• CAS: 66962-64-9
• 化学式: C₂₀H₂₀N₂O₇
• 分子量: 400.388
• InChiKey: FPXLOIYVAFTLKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-hydroxy-5-norbornene-2,3-dicarboximide ester of N-benzyloxycarbonyl-DL-2-hydroxy-3-aminopropanoic acid 、 1,2',6'-tri-N-(benzyloxycarbonyl)fortimicin B 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 48.0h， 以1.08 g的产率得到1,2',6',3''-N-benzyloxycarbonyl-4-N-(D,L-3-amino-2-hydroxypropanoyl)fortimicin B
  参考文献：
  名称：

  4-N-acylfortimicins b and the preparation of fortimicin a from fortimicin B

  摘要：

  Selective 4-N-acylation of fortimicin B (2) has been accomplished by 4-N-acylation of 1,2',6'-tri-N-benzyloxycarbonylfortimicin B (4) followed by hydrogenolysis of the N-protecting benzyloxycarbonyl groups. In this manner, fortimicin B was converted into fortimicin A (1), and a series of 4-N-acylfortimicins B (3) was prepared for antibacterial assay. The key intermediate, 1,2',6'-tri-N-benzyloxycarbonylfortimicin B, was prepared either directly from fortimicin B or by converting fortimicin A into 1,2',6',2''-tetra-N-benzyloxycarbonylfortimicin A (6a), followed by selective hydrolysis of the 4-N-(N-benzyloxycarbonyl)glycyl group of the latter.

  DOI：

  10.1016/s0008-6215(00)85134-4
• 作为产物：
  描述：

  N-羟基-5-降冰片烯-2,3-二甲酰亚胺 、 3-(苄氧基羰基)-2-羟基丙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 N-hydroxy-5-norbornene-2,3-dicarboximide ester of N-benzyloxycarbonyl-DL-2-hydroxy-3-aminopropanoic acid
  参考文献：
  名称：

  4-N-acylfortimicins b and the preparation of fortimicin a from fortimicin B

  摘要：

  Selective 4-N-acylation of fortimicin B (2) has been accomplished by 4-N-acylation of 1,2',6'-tri-N-benzyloxycarbonylfortimicin B (4) followed by hydrogenolysis of the N-protecting benzyloxycarbonyl groups. In this manner, fortimicin B was converted into fortimicin A (1), and a series of 4-N-acylfortimicins B (3) was prepared for antibacterial assay. The key intermediate, 1,2',6'-tri-N-benzyloxycarbonylfortimicin B, was prepared either directly from fortimicin B or by converting fortimicin A into 1,2',6',2''-tetra-N-benzyloxycarbonylfortimicin A (6a), followed by selective hydrolysis of the 4-N-(N-benzyloxycarbonyl)glycyl group of the latter.

  DOI：

  10.1016/s0008-6215(00)85134-4

文献信息

• US4347354A
  申请人：——

  公开号：US4347354A

  公开（公告）日：1982-08-31
• US4424343A
  申请人：——

  公开号：US4424343A

  公开（公告）日：1984-01-03
• 4-N-acylfortimicins b and the preparation of fortimicin a from fortimicin B
  作者：Jack Tadanier、Jerry R. Martin、Paul Kurath、Alma W. Goldstein、Paulette Johnson

  DOI：10.1016/s0008-6215(00)85134-4

  日期：1980.2

  Selective 4-N-acylation of fortimicin B (2) has been accomplished by 4-N-acylation of 1,2',6'-tri-N-benzyloxycarbonylfortimicin B (4) followed by hydrogenolysis of the N-protecting benzyloxycarbonyl groups. In this manner, fortimicin B was converted into fortimicin A (1), and a series of 4-N-acylfortimicins B (3) was prepared for antibacterial assay. The key intermediate, 1,2',6'-tri-N-benzyloxycarbonylfortimicin B, was prepared either directly from fortimicin B or by converting fortimicin A into 1,2',6',2''-tetra-N-benzyloxycarbonylfortimicin A (6a), followed by selective hydrolysis of the 4-N-(N-benzyloxycarbonyl)glycyl group of the latter.