3-O-methanesulfonyl-4-O-acetyl-6-deoxy-6-azido-2,5-anhydro-L-idofuranose dimethylacetal | 959866-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-methanesulfonyl-4-O-acetyl-6-deoxy-6-azido-2,5-anhydro-L-idofuranose dimethylacetal
• 英文别名: [(2S,3R,4S,5R)-2-(azidomethyl)-5-(dimethoxymethyl)-4-methylsulfonyloxyoxolan-3-yl] acetate
• CAS: 959866-72-9
• 化学式: C₁₁H₁₉N₃O₈S
• 分子量: 353.353
• InChiKey: NTWFGBUQCVCNPV-QCLAVDOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-methanesulfonyl-4-O-acetyl-6-deoxy-6-azido-2,5-anhydro-L-idofuranose dimethylacetal 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium tetrahydroborate 、 18-冠醚-6 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 4,6-dideoxy-4-(thymin-1-yl)-6-acetylamino-2,5-anhydro-L-mannitol
  参考文献：
  名称：

  A concise synthesis of 4,6-dideoxy-4-base-6-amino-2,5-anhydro-l-mannitols

  摘要：

  3,6-Di-O-methanesulfonyl-2,5-anhydro-L-idofuranose dimethyl acetal 9 was reacted with NaN3 in DMF to give 6-azido substituted carbohydrate 10 selectively. A series of 6-amino-isonucleosides 4a-d were synthesized by the reaction of nucleobases with epoxide 13, followed by hydrolysis, reduction, and deprotection, in good yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.08.032
• 作为产物：
  描述：

  3,6-di-O-methanesulfonyl-2,5-anhydro-L-idofuranose dimethylacetal 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 81.0h， 生成 3-O-methanesulfonyl-4-O-acetyl-6-deoxy-6-azido-2,5-anhydro-L-idofuranose dimethylacetal
  参考文献：
  名称：

  A concise synthesis of 4,6-dideoxy-4-base-6-amino-2,5-anhydro-l-mannitols

  摘要：

  3,6-Di-O-methanesulfonyl-2,5-anhydro-L-idofuranose dimethyl acetal 9 was reacted with NaN3 in DMF to give 6-azido substituted carbohydrate 10 selectively. A series of 6-amino-isonucleosides 4a-d were synthesized by the reaction of nucleobases with epoxide 13, followed by hydrolysis, reduction, and deprotection, in good yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.08.032

文献信息

• A Convenient Preparation of 5-Iodo-1,4-disubstituted-1,2,3-triazole: Multicomponent One-Pot Reaction of Azide and Alkyne Mediated by CuI−NBS
  作者：Lingjun Li、Guisheng Zhang、Anlian Zhu、Lihe Zhang

  DOI：10.1021/jo800035v

  日期：2008.5.1

  The system of CuI and NBS was found to provide both I+ and Cu+ for the first time. An efficient method for preparation of 5-iodo-1,4-disubstituted-1,2,3-triazole was achieved by multicomponent one-pot reaction of azides with alkynes in the presence of the novel CuI and NBS catalytic system. The high tolerance of various sensitive groups revealed the potential applications of this method in organic

  发现CuI和NBS系统首次提供I +和Cu +。在新型CuI和NBS催化体系的存在下，通过叠氮化物与炔烃的多组分一锅反应，实现了制备5-碘-1,4-二取代-1,2,3-三唑的有效方法。各种敏感性基团的高耐受性揭示了该方法在有机合成和药物发现中的潜在应用。