2,5-di-O-methanesulfonyl-1,4:3,6-dianhydro-D-sorbitol | 24808-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 2,5-di-O-methanesulfonyl-1,4:3,6-dianhydro-D-sorbitol
• 英文别名: 1,4:3,6-dianhydro-2,5-di-O-mesyl-D-glucitol；2,5-di-O-mesyl-D-glucitol；isosorbide 2,5-dimesylate；bis-O-methanesulfonyl-1,4;3,6-dianhydro-D-glucitol；Bis-O-methansulfonyl-1,4;3,6-dianhydro-D-glucit；[(3S,3aS,6R,6aS)-6-methylsulfonyloxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] methanesulfonate
• CAS: 24808-20-6
• 化学式: C₈H₁₄O₈S₂
• 分子量: 302.326
• InChiKey: CFHDLWAMOHQNTF-ULAWRXDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,5-di-O-methanesulfonyl-1,4:3,6-dianhydro-D-sorbitol 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 40.0h， 生成 2-((3aR,6aS)-5-(4-methylphenyl)-3a,6a-dihydro-1H-pyrrolo[3,4-d]triazolyl-4,6-dion)-5-O-mesyl-1,4:3,6-dianhydro-L-iditol
  参考文献：
  名称：

  3+2-Dipolar cycloaddition of dianhydrohexitol azidoderivatives with N-arylmaleimides

  摘要：

  Dianhydrohexitol azides dipolar 3+2 cycloaddition with N-arylmaleimides has been studied with NMR (H-1 and C-13, COSY, NOESY and HSQC) and X-ray analysis. In spite of low asymmetrical induction in this reaction, diastereomerically pure products have been obtained. These products are interesting over their structural similarity to griseolic acid derivatives and dihydropyrrolotriazoles, significant for pharmaceutics. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2015.07.027
• 作为产物：
  描述：

  异山梨醇 在 吡啶 、 甲基磺酰氯 作用下， 生成 2,5-di-O-methanesulfonyl-1,4:3,6-dianhydro-D-sorbitol
  参考文献：
  名称：

  75.多元醇的酸酐。X部分.将葡糖胺转化为1:4-脱水山梨糖醇。亚苄基1：4-脱水山梨醇的结构

  摘要：

  DOI：

  10.1039/jr9480000299

文献信息

• 异山梨醇—单咪唑盐类化合物及其制备方法
  申请人：云南民族大学

  公开号：CN106478653B

  公开（公告）日：2018-10-12

  本发明公开了一系列具有结构通式（如图Ⅰ或Ⅱ）的异山梨醇—单咪唑盐类化合物及其制备方法，以异山梨醇为原料，与甲磺酰氯在无水吡啶条件下转换为异山梨醇甲磺酸酯，接着与2‑甲基咪唑或5,6‑二甲基苯并咪唑在无水DMF溶剂中加热反应合成异山梨醇—单咪唑，在此基础上与溴代烷烃在甲苯溶剂中回流反应合成了异山梨醇—单咪唑盐类化合物。该类化合物表现出了较好的镇痛作用。
• A low molecular weight hydro and organogelator derived from an isohexide and sol–gel transcription of the alcogel
  作者：Steven J. Craythorne、Ciara L. Pollock、Alexander J. Blake、Mark Nieuwenhuyzen、Andrew C. Marr、Patricia C. Marr

  DOI：10.1039/b814274b

  日期：——

  Heating 2,5-di-O-methanesulfonyl-1,4:3,6-dianhydro-D-sorbitol (1) in a range of solvents led to the formation of a gel state at low concentrations. 1 was found to gel aromatics, alcohols and water. The structure of 1 in the solid state was solved by single crystal X-ray crystallography; no strong hydrogen bonds or associated solvents were found in the crystal. Electron micrographs revealed the morphology of the gels to be predominantly rod-like. The ethanol alcogel was used to template silica by sol–gel transcription.

  在一系列溶剂中加热 2,5-二-O-甲磺酰基-1,4:3,6-二氢-D-山梨糖醇（1），可在低浓度下形成凝胶状态。研究发现，1 可以凝胶化芳烃、醇和水。通过单晶 X 射线晶体学研究解决了 1 的固态结构；在晶体中没有发现强氢键或相关溶剂。电子显微照片显示凝胶的形态主要呈棒状。乙醇醇凝胶被用来通过溶胶转录法模板化二氧化硅。
• Low molecular weight gelators (LMWGs) for ionic liquids: the role of hydrogen bonding and sterics in the formation of stable low molecular weight ionic liquid gels
  作者：Peter McNeice、Yingying Zhao、Jianxun Wang、Gerald F. Donnelly、Patricia C. Marr

  DOI：10.1039/c7gc02053h

  日期：——

  of forming a gel with an ionic liquid are rare. We report the ability of 3 sugar based gelators from renewable resources (derived from isosorbide and mannitol) to form gels with 21 ionic liquids comprising a range of cations and anions that are commonly applied in a variety of technologies. It was found that the combined consideration of Kamlet–Taft values with ionic liquid size and shape gives a useful

  能够与离子液体形成凝胶的低分子量胶凝剂很少。我们报告了来自可再生资源（源自异山梨醇和甘露醇）的3种基于糖的胶凝剂与21种离子液体形成凝胶的能力，这些离子液体包含一系列在各种技术中通常应用的阳离子和阴离子。研究发现，将Kamlet-Taft值与离子液体的大小和形状结合起来考虑，可以为成功形成凝胶提供有用的预测指标。
• 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.
• 264. Anhydrides of polyhydric alcohols. Part XV. The reactions of sodium iodide and lithium chloride with dimethanesulphonyl and ditoluene-p-sulphonyl derivatives of the 1 : 4-3 : 6-dianhydrides of D-mannitol, D-sorbitol, and L-iditol
  作者：L. F. Wiggins、D. J. C. Wood

  DOI：10.1039/jr9510001180

  日期：——