2,5-diazido-2,5-dideoxy-D-mannitol | 76753-17-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2,5-diazido-2,5-dideoxy-D-mannitol
• 英文别名: (2R,3R,4R,5R)-2,5-diazidohexane-1,3,4,6-tetrol
• CAS: 76753-17-8
• 化学式: C₆H₁₂N₆O₄
• 分子量: 232.199
• InChiKey: AJDVVWLIZKCKGI-KVTDHHQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,5-diazido-2,5-dideoxy-D-mannitol 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 (3R,3aR,6R,6aR)-3,6-diazidohexahydrofuro[3,2-b]furan
  参考文献：
  名称：

  Synthesis and biological activity of 1,4:3,6-dianhydro-2,5-diazido-2,5-dideoxyhexitols

  摘要：

  Reaction of 1,4:3,6-dianhydro-2,5-di-O-mesyl- and -tosyl-D-mannitol with sodium azide afforded the 2,5-diazido-L-iditol derivative. The analogous D-glucitol isomer was obtained in a similar reaction starting from the corresponding D-glucitol derivatives, and showed significant, hypnotic activity in animals. For establishing the structure-activity relationship, 1,4:3,6-dianhydro-2,5-diazido-2,5-dideoxy-L-mannitol (19), as well as its antipode 27 [1,4:3,6-dianhydro-2,5-diazido-2,5-dideoxy-D-mannitol] was synthesized, starting from D-mannitol. Compound 19 was as effective as Doriden (3-ethyl-3-phenylglutarimide), a hypnotic drug. The antipode 27 and the bioisosteric 1(4),3(6)-dithio derivative were inactive.

  DOI：

  10.1016/s0008-6215(00)84675-3
• 作为产物：
  描述：

  1,6-di-O-benzoyl-3,4-O-isopropylidene-L-iditol 在 吡啶 、 盐酸 、 sodium azide 、 酚酞 、 sodium methylate 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.0h， 生成 2,5-diazido-2,5-dideoxy-D-mannitol
  参考文献：
  名称：

  Synthesis and biological activity of 1,4:3,6-dianhydro-2,5-diazido-2,5-dideoxyhexitols

  摘要：

  Reaction of 1,4:3,6-dianhydro-2,5-di-O-mesyl- and -tosyl-D-mannitol with sodium azide afforded the 2,5-diazido-L-iditol derivative. The analogous D-glucitol isomer was obtained in a similar reaction starting from the corresponding D-glucitol derivatives, and showed significant, hypnotic activity in animals. For establishing the structure-activity relationship, 1,4:3,6-dianhydro-2,5-diazido-2,5-dideoxy-L-mannitol (19), as well as its antipode 27 [1,4:3,6-dianhydro-2,5-diazido-2,5-dideoxy-D-mannitol] was synthesized, starting from D-mannitol. Compound 19 was as effective as Doriden (3-ethyl-3-phenylglutarimide), a hypnotic drug. The antipode 27 and the bioisosteric 1(4),3(6)-dithio derivative were inactive.

  DOI：

  10.1016/s0008-6215(00)84675-3

文献信息

• US4332818A
  申请人：——

  公开号：US4332818A

  公开（公告）日：1982-06-01
• Synthesis and biological activity of 1,4:3,6-dianhydro-2,5-diazido-2,5-dideoxyhexitols
  作者：János Kuszmann、Gábor Medgyes

  DOI：10.1016/s0008-6215(00)84675-3

  日期：1980.10

  Reaction of 1,4:3,6-dianhydro-2,5-di-O-mesyl- and -tosyl-D-mannitol with sodium azide afforded the 2,5-diazido-L-iditol derivative. The analogous D-glucitol isomer was obtained in a similar reaction starting from the corresponding D-glucitol derivatives, and showed significant, hypnotic activity in animals. For establishing the structure-activity relationship, 1,4:3,6-dianhydro-2,5-diazido-2,5-dideoxy-L-mannitol (19), as well as its antipode 27 [1,4:3,6-dianhydro-2,5-diazido-2,5-dideoxy-D-mannitol] was synthesized, starting from D-mannitol. Compound 19 was as effective as Doriden (3-ethyl-3-phenylglutarimide), a hypnotic drug. The antipode 27 and the bioisosteric 1(4),3(6)-dithio derivative were inactive.