반응 #351061

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2,6-Dichloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)benzimidazole

→

67

2,6-Dichloro-I-(βribofuranosyl)benzimidazole

용매

ammonia

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후처리

1. 1
   기타Volatile materials were evaporated in vacuo
2. 2
   기타to provide a white powdery precipitate
3. 3
   기타This residue was recrystallized from MeOH

실험 절차

2,6-Dichloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)benzimidazole (66) (1.8 grams) was dissolved in methanolic ammonia (35 ml). The reaction material was stirred in a pressure bottle for 5 hours at room temperature. Volatile materials were evaporated in vacuo to provide a white powdery precipitate. This residue was recrystallized from MeOH to yield 561 mg (2 crops, 85%) of 67 as colorless needles. MP 162°-163° C. 1H NMR (DMSO-d6): d 8.30 (d, 1, 7-H, J7-5 =2.0 Hz), 7.64 (d, 1, 4-H, J4-5 =8.5 Hz), 7.31 (dd, 1, 5-H), 5.89 (d, 1, 1'-H, J1'-2' =8.0 Hz), 5.49 (d, 1, 2'-OH, J2'-2' =6 5 Hz), 5.35 (t, 1, 5'-OH, J5'-5'OH =5.0 Hz), 5.28 (d, 1, 3'-OH, J3'-3'OH =4.5 Hz), 4.46 (m, 1, 2'-H, J2'-3' =5.-5 Hz), 4.14 (m, 1, 3'-H, J3'-4' =2.0 Hz), 4.00 (m, 1, 4'-H, J4'-5' =J4'-5" =3.0 Hz), 3.70 (m, 2, 5'-H and 5"-H, J5'-5" =12.0 Hz). 13C NMR (DMSO-d6) d 140.72 (C2), 140.17 (C3a), 133.56 (C7a), 127.86 (C6), 123.23 (C5), 128.34 (C6), 120.03 (C4), 113.15 (C7), 89.00 (C1'), 86.26 (C4'), 71.37 (C2'), 69.72 (C3'), 61.12 (C5').

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