9-(4',6'-O-benzylidene-β-D-glucopyranosyl)-H-6-chloropurine | 1000376-94-2

• 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-β-D-glucopyranosyl)-H-6-chloropurine
• 英文别名: (2R,4aR,6R,7R,8R,8aS)-6-(6-chloropurin-9-yl)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 1000376-94-2
• 化学式: C₁₈H₁₇ClN₄O₅
• 分子量: 404.81
• InChiKey: FQZGPNJMKVOPJU-SRXKGNOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  6-Chloro-9-β-D-glucopyranosilpurin 、 苯甲醛二甲缩醛 在 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以230 mg的产率得到9-(4',6'-O-benzylidene-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.