N-[9-[(2R,4S,5R)-4-羟基-5-(苯基甲氧基甲基)四氢呋喃-2-基]嘌呤-6-基]苯甲酰胺 | 130359-85-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: N-[9-[(2R,4S,5R)-4-羟基-5-(苯基甲氧基甲基)四氢呋喃-2-基]嘌呤-6-基]苯甲酰胺
• 英文名称: 9-(5-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-N-benzoyladenine
• 英文别名: 6-N-Benzoyl-5'-O-benzyl-2'-deoxyadenosine；N-[9-[(2R,4S,5R)-4-hydroxy-5-(phenylmethoxymethyl)oxolan-2-yl]purin-6-yl]benzamide
• CAS: 130359-85-2
• 化学式: C₂₄H₂₃N₅O₄
• 分子量: 445.478
• InChiKey: ABXIKYZXEAGUBB-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2R,3S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((benzyloxy)methyl)tetrahydrofuran-3-yl acetylglycinate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以87%的产率得到N-[9-[(2R,4S,5R)-4-羟基-5-(苯基甲氧基甲基)四氢呋喃-2-基]嘌呤-6-基]苯甲酰胺
  参考文献：
  名称：

  Highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides via a 3′-(N-acetyl)-glycyl-directing group

  摘要：

  A facile synthesis of 2'-deoxy-beta-ribonucleosides from 3'-O-(N-acetyl)-glycyl-protected 2'-deoxyribofuranose has been developed. The coupling reactions between the protected 2'-deoxyribose and silylated bases exhibited beta-selectivity up to 98% presumably via a 1',3'-participation mechanism. The 3'-directing group can be introduced and removed easily under mild conditions. This approach provides an efficient and highly stereoselective entry for the synthesis of 2'-deoxy-ribonucleosides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.006

文献信息

• An asymmetric approach to 2-deoxynucleosides via organosulfur building blocks as chemical chameleons
  作者：Barry M. Trost、Christoph Nübling

  DOI：10.1016/0008-6215(90)84067-5

  日期：1990.7

  asymmetric synthesis of 6-N-benzoyl-5'-O-benzyl-2'-deoxyadenosine and its a anomer from non-carbohydrate building blocks is achieved in 7 steps. The sequence builds the basic structures using bis(methylthio)methane and methylthiomethyl phenyl sulfone as both nucleophilic and electrophilic building blocks, a feature that suggests their behavior as chemical chameleons. The asymmetric induction is achieved

  由非碳水化合物结构单元实现6-N-苯甲酰基-5'-O-苄基-2'-脱氧腺苷及其异构体的不对称合成可通过7个步骤完成。该序列使用双（甲硫基）甲烷和甲硫基甲基苯基砜作为亲核和亲电构件来构建基本结构，这一特征表明它们作为化学变色龙的行为。利用基于催化不对称环氧化的动力学拆分来实现不对称诱导。
• TROST, BARRY M.;NUBLING, CHRISTOPH, CARBOHYDR. RES., 202,(1990) C. 1-12
  作者：TROST, BARRY M.、NUBLING, CHRISTOPH

  DOI：——

  日期：——
• Highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides via a 3′-(N-acetyl)-glycyl-directing group
  作者：Zhaogui Liu、Deyao Li、Biaolin Yin、Jiancun Zhang

  DOI：10.1016/j.tetlet.2009.09.006

  日期：2010.1

  A facile synthesis of 2'-deoxy-beta-ribonucleosides from 3'-O-(N-acetyl)-glycyl-protected 2'-deoxyribofuranose has been developed. The coupling reactions between the protected 2'-deoxyribose and silylated bases exhibited beta-selectivity up to 98% presumably via a 1',3'-participation mechanism. The 3'-directing group can be introduced and removed easily under mild conditions. This approach provides an efficient and highly stereoselective entry for the synthesis of 2'-deoxy-ribonucleosides. (C) 2009 Elsevier Ltd. All rights reserved.