methyl 1-[2-chloroadenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate | 1012864-69-5

• 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: methyl 1-[2-chloroadenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate
• 英文别名: methyl (2S,3S,4R,5R)-3,4-diacetyloxy-5-(6-amino-2-chloropurin-9-yl)oxolane-2-carboxylate
• CAS: 1012864-69-5
• 化学式: C₁₅H₁₆ClN₅O₇
• 分子量: 413.774
• InChiKey: JIRJQIDAAIFSBK-MPXOCVNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 1-[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65%的产率得到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
• 作为产物：
  描述：

  beta-D-呋喃核糖酸甲酯三乙酸酯 、 2-氯-6-氨基嘌呤 在 硫酸氢铵 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 、 1,2-二氯乙烷 为溶剂， 反应 16.33h， 以89%的产率得到methyl 1-[2-chloroadenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate
  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.