1,6-di-O-benzoyl-3,4-O-isopropylidene-L-iditol | 76753-14-5

• 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: 1,6-di-O-benzoyl-3,4-O-isopropylidene-L-iditol
• 英文别名: 1,6-Dibenzoyl-3,4-isopropylidene-L-iditol；[(2S)-2-[(4R,5R)-5-[(1S)-2-benzoyloxy-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl] benzoate
• CAS: 76753-14-5
• 化学式: C₂₃H₂₆O₈
• 分子量: 430.455
• InChiKey: PBBWGCYLZSQEET-VNTMZGSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  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 98.5h， 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：

  苯甲酸 、 1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol 在 sodium benzoate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以55%的产率得到1,6-di-O-benzoyl-3,4-O-isopropylidene-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

• 1,4;3,6-Dianhydro-2,5-diazido-2,5-dideoxy-hexitols
  申请人：Egyt Gyogyszervegyeszeti Gyar

  公开号：US04332818A1

  公开（公告）日：1982-06-01

  The invention relates to new stereoisomeric 1,4;3,6-dianhydro-2,5-diazido-2,5-dideoxy-hexitols of the Formula I. These compounds can be prepared by (a) reacting a hexitol derivative of the general Formula II /wherein R is a mesyl or tosyl group/ in an aqueous or anhydrous organic solvent with an alkali metal azide or ammonium azide; or (b) mesylating or tosylating a compound of the Formula III and treating the mixed ester of the general Formula IV thus obtained /wherein R is as stated above/ with a base; or (c) subjecting a compound of the Formula III to debenzoylation and subsequently to partial esterification and treating the compound of the general Formula V thus obtained /wherein R is as stated above/ with a base. The new compounds of the Formula I possess valuable hypnotic properties and can be used in therapy. ##STR1##

  本发明涉及新的立体异构体1,4;3,6-二脱水-2,5-二叠氮基-2,5-二脱氧己糖的化合物，化学式为I。这些化合物可以通过以下方法制备：（a）在水性或无水有机溶剂中，用碱金属叠氮化物或氨叠氮化物与一般化学式II的己糖衍生物（其中R为甲烷基磺酰基或对甲苯磺酰基）反应；或（b）对式III的化合物进行甲烷基化或对甲苯基化，然后用碱处理得到一般式IV的混合酯（其中R如上所述）；或（c）将式III的化合物进行去苯甲酰化，然后进行部分酯化，用碱处理得到一般式V的化合物（其中R如上所述）。化合物I具有有价值的催眠作用，可用于治疗。
• 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.