6-deoxy-6-acetylamino-2,5:3,4-dianhydro-L-talose dimethylacetal | 959866-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 6-deoxy-6-acetylamino-2,5:3,4-dianhydro-L-talose dimethylacetal
• 英文别名: N-[[(1R,2S,4R,5R)-4-(dimethoxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]methyl]acetamide
• CAS: 959866-74-1
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: NWWRCWKOBFROTG-JQCXWYLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-deoxy-6-acetylamino-2,5:3,4-dianhydro-L-talose dimethylacetal 在 盐酸 、 sodium tetrahydroborate 、 18-冠醚-6 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 4,6-dideoxy-4-(adenin-9-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 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 108.5h， 生成 6-deoxy-6-acetylamino-2,5:3,4-dianhydro-L-talose 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 concise synthesis of 4,6-dideoxy-4-base-6-amino-2,5-anhydro-l-mannitols
  作者：Fang Wang、Zhen-Jun Yang、Hong-Wei Jin、Liang-Ren Zhang、Li-He Zhang

  DOI：10.1016/j.tetasy.2007.08.032

  日期：2007.9

  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.