反应 #1596985

ord-9eccb341ab11418ea4bb6eda726ba468

反应方程式

C=CCn1c(=O)n([C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]2OC(C)=O)c2nc(N)nc(Cl)c21
Compound 41
C=CCn1c(=O)n([C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]2OC(C)=O)c2nc(N)nc(Cl)c21
7-Allyl-2-amino-6-chloro-9-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-7,9-dihydro-purin-8-one
C=CCn1c(=O)n([C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]2OC(C)=O)c2nc(N)ncc21
42
收率 60.0%
C=CCn1c(=O)n([C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]2OC(C)=O)c2nc(N)ncc21
7-Allyl-2-amino-9-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-7,9-dihydro-purin-8-one
收率 60.0%

反应条件

温度
70°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    过滤The suspended particles were filtered off
  2. 2
    浓缩the filtrate concentrated under vacuum
  3. 3
    其他The residue was purified by flash chromatography
  4. 4
    其他The solvent was removed

实验过程

Compound 41 (0.27 g, 0.56 mmol) was dissolved in acetic acid and Zn—Cu couple was added to the solution. The mixture was heated at 70° C. for 18 h. The suspended particles were filtered off and the filtrate concentrated under vacuum. The residue was purified by flash chromatography using 10% to 100% gradient of ethyl acetate in hexanes. The solvent was removed to give 150 mg (60%) of 42 as off-white solid: 1H NMR (400 MHz, CDCl3) δ 6.05 (t, J=4.0 Hz, 1H), 6.03 (d, J=4.0 Hz, 1H), 5.87 (t, J=6.0 Hz, 1H), 5.83 (m, 1H), 5.48 (br s, 2H), 5.33 (s, 1H), 5.29 (d, J=5.6 Hz, 1H), 4.49 (d, J=3.2 Hz, 1H), 4.46 (d, J=3.2 Hz, 1H), 4.41 (d, J=5.6 Hz, 2H), 4.27 (m, 2H), 2.12 (s, 3H), 2.10 (s, 3H), 2.05 (s, 3H); MS (+)-ES [M+H]+ 450.0 m/z.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08211863B2uspto-grants-2012_07