5,6-Dichloro-2-ethynyl-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl) 1H-benzimidazole → 5,6-Dichloro-2-ethenyl-1-(5deoxy-beta-D-ribofuranosyl)-1H-benzimidazole

HRID 2227203Notes

Reaction equation

HRID 2227203 reaction equation
[Cl:1][C:2]1[C:26]([Cl:27])=[CH:25][C:5]2[N:6]([C@@H:11]3[O:23][C@H:22]([CH3:24])[C@@H:17]([O:18]C(=O)C)[C@H:12]3[O:13]C(=O)C)[C:7]([C:9]#[CH:10])=[N:8][C:4]=2[CH:3]=1>ClCCl>[Cl:1][C:2]1[C:26]([Cl:27])=[CH:25][C:5]2[N:6]([C@@H:11]3[O:23][C@H:22]([CH3:24])[C@@H:17]([OH:18])[C@H:12]3[OH:13])[C:7]([CH:9]=[CH2:10])=[N:8][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 570077735,6-Dichloro-2-ethynyl-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl) 1H-benzimidazole

Product 1

HCID 220862725,6-Dichloro-2-ethenyl-1-(5deoxy-beta-D-ribofuranosyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5,6-Dichloro-2-ethynyl-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl) 1H-benzimidazole (0.85 g, 0.20 mmol) was deprotected using general procedure III. Crude product was purified by silica gel chromatography using 1:10 methanol:dichloromethane to give the title compound as an off white solid (0.04 g, 0.12 mmol, 59%); MS (ES+): m/z (rel. intensity) 351 (15, M++Na);

Workup

  1. customCrude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0613439ebe75493796c58bfecc8ad927
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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