[(2S,3S,4R,5R)-4-acetyloxy-2-(ethylcarbamoyl)-5-methoxyoxolan-3-yl] acetate | 379222-49-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3S,4R,5R)-4-acetyloxy-2-(ethylcarbamoyl)-5-methoxyoxolan-3-yl] acetate
• CAS: 379222-49-8
• 化学式: C₁₂H₁₉NO₇
• 分子量: 289.285
• InChiKey: IVMKGCNSYBBZOU-DTHBNOIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4R,5R)-4-acetyloxy-2-(ethylcarbamoyl)-5-methoxyoxolan-3-yl] acetate 在 ammonium sulfate 、 硫酸 、 六甲基二硅氮烷 作用下， 生成 2,3-di-O-acetyl-1-deoxy-1-(2,6-dichloro-9H-purin-9-yl) N-ethyl-β-D-ribofuranuronamide
  参考文献：
  名称：

  COUPLING OF 2,6-DISUBSTITUTED PURINES TO RIBOSE-MODIFIED SUGARS

  摘要：

  1,2,3-Tri-O-acetyl-N-ethyl-beta -D-ribofuranuronamide was synthesized in three steps starting from 1-O-methyl-(2,3-O-isopropylidene)-beta -D-ribofuranuronic acid. Both the triacetyl and the 1-O-methyl-2,3-di-O-acetyl derivatives were coupled to the 2,6-dichloropurine to obtain the acetylated 1-(2,6-dichloro-9H-purin-9-yl)- 1-deoxy-N-ethyl-beta -D-erythro-pentofuranuronamide. H-1 NMR and n.O.e. data accounted for both anomeric and N-7/N-9 isomeric configuration.

  DOI：

  10.1081/ncn-100002427
• 作为产物：
  描述：

  (3AS,4S,6R,6AR)-N-ethyl-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide 在 吡啶 、 Dowex 50 (H⁺) 作用下， 以 甲醇 为溶剂， 生成 [(2S,3S,4R,5R)-4-acetyloxy-2-(ethylcarbamoyl)-5-methoxyoxolan-3-yl] acetate
  参考文献：
  名称：

  COUPLING OF 2,6-DISUBSTITUTED PURINES TO RIBOSE-MODIFIED SUGARS

  摘要：

  1,2,3-Tri-O-acetyl-N-ethyl-beta -D-ribofuranuronamide was synthesized in three steps starting from 1-O-methyl-(2,3-O-isopropylidene)-beta -D-ribofuranuronic acid. Both the triacetyl and the 1-O-methyl-2,3-di-O-acetyl derivatives were coupled to the 2,6-dichloropurine to obtain the acetylated 1-(2,6-dichloro-9H-purin-9-yl)- 1-deoxy-N-ethyl-beta -D-erythro-pentofuranuronamide. H-1 NMR and n.O.e. data accounted for both anomeric and N-7/N-9 isomeric configuration.

  DOI：

  10.1081/ncn-100002427