N⁶-benzyl-2-chloroadenosine-5'-N-methyl uronamide | 1012864-76-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁶-benzyl-2-chloroadenosine-5'-N-methyl uronamide
• 英文别名: (2S,3S,4R,5R)-5-[6-(benzylamino)-2-chloropurin-9-yl]-3,4-dihydroxy-N-methyloxolane-2-carboxamide
• CAS: 1012864-76-4
• 化学式: C₁₈H₁₉ClN₆O₄
• 分子量: 418.84
• InChiKey: PAMJIPZGEMDABX-PFHKOEEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 1-[N⁶-benzyl-2-chloroadenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate 、 甲胺 以 四氢呋喃 为溶剂， 反应 0.33h， 以60%的产率得到N⁶-benzyl-2-chloroadenosine-5'-N-methyl uronamide
  参考文献：
  名称：

  An efficient convergent synthesis of adenosine-5′-N-alkyluronamides

  摘要：

  Herein we report an efficient synthesis of adenosine-5'-N-alkyluronamides in which an enzyme-mediated deacetylation reaction is a key to the selective modification of the 5'-N-position, prior to coupling the ribose and purine components via a microwave-assisted Vorbruggen coupling. This approach provides access to highly functionalised adenosines with 2- and N-6-substitutents, which can be incorporated before or after the ribose-coupling step. In all cases the microwave-assisted Vorbruggen coupling conditions afforded anomerically pure purine ribosides in good to excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.100

文献信息

• An efficient convergent synthesis of adenosine-5′-N-alkyluronamides
  作者：Shane M. Devine、Peter J. Scammells

  DOI：10.1016/j.tet.2007.11.100

  日期：2008.2

  Herein we report an efficient synthesis of adenosine-5'-N-alkyluronamides in which an enzyme-mediated deacetylation reaction is a key to the selective modification of the 5'-N-position, prior to coupling the ribose and purine components via a microwave-assisted Vorbruggen coupling. This approach provides access to highly functionalised adenosines with 2- and N-6-substitutents, which can be incorporated before or after the ribose-coupling step. In all cases the microwave-assisted Vorbruggen coupling conditions afforded anomerically pure purine ribosides in good to excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.