2,5-diazido-1,6-di-O-benzoyl-2,5-dideoxy-L-iditol | 76753-12-3

• 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: 2,5-diazido-1,6-di-O-benzoyl-2,5-dideoxy-L-iditol
• 英文别名: 2,5-diazido-1,6-di-O-benzoyl-2,5-dideoxy-L-iditiol；2,5-diazido-1,6-dibenzoyl-2,5-dideoxy-L-iditol；(2S,3R,4R,5S)-2,5-diazido-6-(benzoyloxy)-3,4-dihydroxyhexyl benzoate；[(2S,3R,4R,5S)-2,5-diazido-6-benzoyloxy-3,4-dihydroxyhexyl] benzoate
• CAS: 76753-12-3
• 化学式: C₂₀H₂₀N₆O₆
• 分子量: 440.415
• InChiKey: YQIZDHJIGSHEHS-WNRNVDISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,5-diazido-1,6-di-O-benzoyl-2,5-dideoxy-L-iditol 在 酚酞 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以79%的产率得到2,5-diazido-2,5-dideoxy-L-iditol
  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：

  2,5-diazido-1,6-di-O-benzoyl-2,5-dideoxy-3,4-O-isopropylidene-L-iditol 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以70%的产率得到2,5-diazido-1,6-di-O-benzoyl-2,5-dideoxy-L-iditol
  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

• Synthesis of sorbistin analogues
  作者：Gábor Medgyes、Gyula Jerkovich、János Kuszmann、Péter Fügedi

  DOI：10.1016/0008-6215(89)84037-6

  日期：1989.3

  D-Galactose was converted into the glycosylating agents 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-alpha-D-glucopyranosyl chloride (11) and the methyl beta-D-thiopyranoside 19. Condensation of 11 with 2,5-diazido-1,6-di-O-benzoyl-2,5-di-deoxy-L-iditol in the presence of mercury salts gave 24% of 2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-alp ha-D- glucopyranosyl)-1,6-di-O-benzoyl-2

  将D-半乳糖转化为糖基化试剂4-叠氮基2,3-二-O-苄基-4-脱氧-6-O-丙酰基-α-D-吡喃葡萄糖基氯（11）和甲基β-D-硫吡喃糖苷19.在汞盐存在下，将11与2,5-二叠氮基-1,6-二-O-苯甲酰基-2,5-二脱氧-L-ID醇缩合，得到24％的2,5-二叠氮基-3 -O-（4-叠氮基-2,3-二-O-苄基-4-脱氧-6-O-丙酰-alp ha-D-吡喃葡萄糖基）-1,6-二-O-苯甲酰基-2,5-双脱氧-L-iditol。在2,6-二-叔-叔丁基存在下，三氟甲烷磺酸甲酯促进1,3-二叠氮基-2-O-苄基-1,3-二脱氧-5,6-O-异亚丙基-D-古特洛尔与19的糖基化反应。丁基-4-甲基吡啶得到1,3-二叠氮基-4-O-（4-叠氮基-2,3-二-O-苄基-4-脱氧-6-O-丙酰基-alp ha-D-吡喃葡萄糖基）-2 -O-苄基-1,3-二脱氧-5,6-O-异亚丙基-D-古洛糖
• MEDGYES, GABOR;JERKOVICH, GYULA;KUSZMANN, JANOS;FUGEDI, PETER, CARBOHYDR. RES., 186,(1989) N, C. 225-239
  作者：MEDGYES, GABOR、JERKOVICH, GYULA、KUSZMANN, JANOS、FUGEDI, PETER

  DOI：——

  日期：——
• 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.