CAS: 68733-20-0; 1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-α-D-Mannopyranose

该化合物是一种合成碳水化合物衍生物,其特征是存在一个Azido组和多种乙酰组,并附于脱氧甲诺氧基结构.该化合物通常显示白色到白色的晶状表面,在极有机溶剂中可溶解.Azido组(N3)的存在使其在有机合成中成为宝贵的中间体,特别是在可参与各种混合反应的化学应用中.乙酰基组有助于保护羟基功能,增强分子的稳定性和再活性.四乙酰氧基甲氧基环芳诺甘诺甘醇经常用于生物化学研究,特别是在对晶体化过程的研究和为治疗用途开发晶体化合物中.该组的独特结构特征允许有选择性的反应,使其在合成更复杂的甘基分子时成为多用途的建筑块块.与许多乙酰化合物一样,由于潜在的再反应和毒性,应当采取适当的安全措施.

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68733-19-7 56883-33-1 171032-74-9

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    合成工艺路线路线简述

      📜1,3,4,6-Tetra-O-Acetyl Glucopyranose置于吡啶,Sodium Azide体系中,用 二氯甲烷,N,N-二甲基甲酰胺 作为反应溶剂,化学反应 1.5H,反应生成 2-叠氮-2-脱氧-1,3,4,6-四-氧-乙酰-Alpha-D-吡喃甘露糖
      参考文献:1,3,4,6-四-O-乙酰基-2-叠氮基-2-脱氧-α-D-甘露吡喃糖合成方法的改进
      标题:1,3,4,6-四-O-乙酰基-2-叠氮基-2-脱氧-α-D-甘露吡喃糖合成方法的改进
      摘要:为了找到针对脑膜炎奈瑟氏球菌a组的合适的稳定候选疫苗,已经合成了与荚膜多糖有关的几种结构.论文的第一部分描述了从葡萄糖开始的c-膦酸酯类似物的合成.关键步骤是c-膦酸甲酯单体与2-乙酰氨基甘露糖衍生物的6-羟基的mitsunobu偶联.这项工作中包含对2-叠氮基-2-脱氧-D-甘露吡喃糖的改进合成的描述.第二部分概述了脑膜炎奈瑟氏球菌血清型a的天然荚膜多糖中存在的结构元素的合成,包括不同的乙酰化和磷酸化模式.
      DOI:10.1016/j.Carres.2005.09.008

      海关参考信息

      专利信息


      专利号:US-4362720-A
      优先权日:1977-04-14
      标题:Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
      发明人：LEMIEUX RAYMOND U; RATCLIFFE R MURRAY
      权利人:CHEMBIOMED LTD
      摘要:O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.

      专利号:US-4308376-A
      优先权日:1977-04-14
      标 题 :Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
      发明人：LEMIEUX RAYMOND U; RATCLIFFE R MURRAY
      权利人:CHEMBIOMED LTD
      摘要:O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.

      专利号:US-4195174-A
      优先权日:1977-04-14
      标题 :Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals

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      主要参考文献

      参考标题:Ligand Design For Somatostatin Receptor Isoforms 4 And 5
      作者:Arvind Negi,Jian Zhou,Sinclair Sweeney,Paul V. Murphy |发布日期:2019.2
      摘要:Peptidal Peptidomimetics Where Side Chains Of Lysine, Tryptophan, And Phenylalanine (I.E. Functional Epitopes) Are Presented On A Scaffold Or Molecular Framework. However, There Could Be More Structural Information That Would Help Design Ligands Selective For One Or More Of These Isoforms. Here, We Include Synthesis Of New Mimetics And Include Their Evaluation As Ligands For Sstr-4 And Sstr-5. Inhibitors

      合成参考文献


      参考文献:10.1016/j.carres.2005.09.008
      摘要:Teodorović P, Slättegård R, Oscarson S. Improved synthesis of 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-alpha-D-mannopyranose. Carbohydr Res. 2005 Dec 12;340(17):2675–6. doi: 10.1016/j.carres.2005.09.008.
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