反応 #1988706

反応方程式

1-amino-4-phenyl-1,2,3,6-tetrahydropyridine

9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine

ammonia

→

2-Chloro-N-(4-phenyl-1,2,3,6-tetrahydro-1-pyridinyl)adenosine

収率 12.0%

反応条件

後処理

1. 1
   その他The title compound was prepared
2. 2
   その他prepared by the procedure

実験手順

The title compound was prepared according to method A as described above by reacting crude 1-amino-4-phenyl-1,2,3,6-tetrahydropyridine (prepared by the procedure outlined in Example 6) (1.25 g) with 9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.50 g, 3.9 mmol), followed by debenzoylation of the purified product using methanolic ammonia to provide the title 2-Chloro-N-(4-phenyl-1,2,3,6-tetrahydro-1-pyridinyl)adenosine (0.20 g 12%) (after column chromatography) as a foam, 1H NMR (DMSO-d6) δ 3.53-3.70 (4H, m, H-5'a, H-5'b and --CH2 --), 3.94 (1H, q, H-4'), 4.14 (1H, q, H-3'), 4.52 (1H, q, H-2'), 5.07 (1H, t, 5'-0H), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.85 (1H, d, H-1'), 6.15 (1H, br s, vinylic C--H), 7.24-7.51 (5H, m, Ar--H), 8.43 (1H, s, H-8), 9.55 (1H, s, N--H).

出典