反応 #44344

反応方程式

1-Ethynyl-2-methyl-cyclohexanol

2-iodo-NECA

→

5-[6-Amino-2-(1-hydroxy-2-methyl-cyclohexylethynyl)-purin-9-yl]-3,4-dihydroxytetrahydrofuran-2-carboxylic acid ethylamide

収率 65.0%

反応条件

後処理

1. 1
   その他gave JR3177A (8.0 mg) and JR3177B (8.2 mg) (overall yield 65%) as white solids
2. 2
   その他after purification by a silica plug and RP-HPLC

実験手順

The reaction of 1-Ethynyl-2-methyl-cyclohexanol (JR3169B) (100 mg, 0.72 mmol) with 2-iodo-NECA (25 mg, 0.06 mmol) under the general coupling conditions gave JR3177A (8.0 mg) and JR3177B (8.2 mg) (overall yield 65%) as white solids after purification by a silica plug and RP-HPLC. JR3177A: 1H NMR (CD3OD-d4) δ 8.47 (s, 1 H), 6.05 (d, J=6.9 Hz, 1 H), 4.77 (dd, J=6.9 Hz, J=4.9 Hz, 1 H), 4.45 (d, J=1.9 Hz, 1 H), 4.34 (dd, J=4.6 Hz, J=2.1 Hz, 1 H), 3.41 (m, 2 H), 2.13 (d, J=12.7 Hz, 2 H), 1.65 (m, 5 H), 1.32 (m, 2 H), 1.14 (t, J=7.0 Hz, 3 H), 1.13 (d, J=6.6 Hz, 3 H). 13C NMR (CD3OD-d4) δ. APCI m/z (rel intensity) 445.3 (MH+, 100), 427.4 (80), 254.4 (14). 1H NMR (CD3OD-d4) δ 8.49 (s, 1 H), 6.05 (d, J=6.9 Hz, 1 H), 4.78 (dd, J=6.4 Hz, J=4.9 Hz, 1 H), 4.45 (d, J=1.9 Hz, 1 H), 4.34 (dd, J=4.6 Hz, J=1.6 Hz, 1 H), 3.42 (m, 2 H), 2.12 (d, J=12.3 Hz, 2 H), 1.65 (m, 4 H), 1.35 (m, 4 H), 1.14 (t, J=7.3 Hz, 3 H), 1.12 (d, J=6.6 Hz, 3 H). 13C NMR (CD3OD-d4) δ. APCI m/z (rel intensity) 445.7 (MH+, 100), 427.3 (35), 254.4 (3.5).

出典