9-(4',6'-O-benzylidene-2',3'-di-O-trifluoromethanesulfonyl-β-D-glucopyranosyl)-H-6-chloropurine | 1000376-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-(4',6'-O-benzylidene-2',3'-di-O-trifluoromethanesulfonyl-β-D-glucopyranosyl)-H-6-chloropurine
• 英文别名: [(2R,4aR,6R,7R,8S,8aR)-6-(6-chloropurin-9-yl)-2-phenyl-7-(trifluoromethylsulfonyloxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] trifluoromethanesulfonate
• CAS: 1000376-96-4
• 化学式: C₂₀H₁₅ClF₆N₄O₉S₂
• 分子量: 668.936
• InChiKey: XWZJMLVLHQSOIL-NIFYWOHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  175
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  9-(4',6'-O-benzylidene-2',3'-di-O-trifluoromethanesulfonyl-β-D-glucopyranosyl)-H-6-chloropurine 、 四丁基醋酸铵 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以86%的产率得到9-(2',3'-di-O-acetyl-4',6'-O-benzylidene-β-D-altropyranosyl)-H-6-chloropurine
  参考文献：
  名称：

  Facile synthesis of 1′,2′-cis-β-pyranosyladenine nucleosides

  摘要：

  1',2'-cis-O-Glycosyladenine nucleosides, such as beta-altroside, beta-marmoside, and beta-idoside, were efficiently synthesized from the corresponding 1',2'- trans- beta-6-chloropurine derivatives, beta-glucoside, and beta-galactoside. Nucleophilic substitution of the O-tri-fluoromethanesulfonyl groups at the C-2' and/or 3' was carried out using tetrabutylammonium acetate or cesium acetate under mild conditions. Subsequent deprotection and amidation afforded the desired compounds, 1',2'-cis-beta-pyranosyladenine nucleosides. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.08.009
• 作为产物：
  描述：

  9-(4',6'-O-benzylidene-β-D-glucopyranosyl)-H-6-chloropurine 、 三氟甲磺酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以95%的产率得到9-(4',6'-O-benzylidene-2',3'-di-O-trifluoromethanesulfonyl-β-D-glucopyranosyl)-H-6-chloropurine
  参考文献：
  名称：

  Facile synthesis of 1′,2′-cis-β-pyranosyladenine nucleosides

  摘要：

  1',2'-cis-O-Glycosyladenine nucleosides, such as beta-altroside, beta-marmoside, and beta-idoside, were efficiently synthesized from the corresponding 1',2'- trans- beta-6-chloropurine derivatives, beta-glucoside, and beta-galactoside. Nucleophilic substitution of the O-tri-fluoromethanesulfonyl groups at the C-2' and/or 3' was carried out using tetrabutylammonium acetate or cesium acetate under mild conditions. Subsequent deprotection and amidation afforded the desired compounds, 1',2'-cis-beta-pyranosyladenine nucleosides. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.08.009

文献信息

• Facile synthesis of 1′,2′-cis-β-pyranosyladenine nucleosides
  作者：Takayuki Ando、Hisashi Shinohara、Xiong Luo、Mahmoud Kandeel、Yukio Kitade

  DOI：10.1016/j.carres.2007.08.009

  日期：2007.12

  1',2'-cis-O-Glycosyladenine nucleosides, such as beta-altroside, beta-marmoside, and beta-idoside, were efficiently synthesized from the corresponding 1',2'- trans- beta-6-chloropurine derivatives, beta-glucoside, and beta-galactoside. Nucleophilic substitution of the O-tri-fluoromethanesulfonyl groups at the C-2' and/or 3' was carried out using tetrabutylammonium acetate or cesium acetate under mild conditions. Subsequent deprotection and amidation afforded the desired compounds, 1',2'-cis-beta-pyranosyladenine nucleosides. (c) 2007 Elsevier Ltd. All rights reserved.