p-Toluenesulfonate → 3-Pentofuranosyl-3,4,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-7-ol

HRID 261058Notes

Reaction equation

HRID 261058 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.S([O:22][CH2:23][CH:24]1[NH:32][CH:31]=[N:30][C:29]2[N:28]([C@@H:33]3[O:45][C@H:44]([CH2:46][O:47]C(=O)C)[C@@H:39]([O:40]C(=O)C)[C@H:34]3[O:35]C(=O)C)[CH:27]=[N:26][C:25]1=2)(C1C=CC(C)=CC=1)(=O)=O>C(#N)C>[CH2:24]1[C:25]2[N:26]=[CH:27][N:28]([C@@H:33]3[O:45][C@H:44]([CH2:46][OH:47])[C@@H:39]([OH:40])[C@H:34]3[OH:35])[C:29]=2[NH:30][CH:31]=[N:32][CH:23]1[OH:22]

Participants

4

Reactant 2

HCID 85570p-ToluenesulfonateHCID 178476354HCID 178476354, compound

Product 1

HCID 1287573-Pentofuranosyl-3,4,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-7-olYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The tosylate (I, 211 mg) obtained in Example 2 was dissolved in acetonitrile (10 ml) and 0.5 N Ba(OH)2 (10 ml) was added. The homogeneous brown solution was then stirred for 4 hr, when no tosylate (I) was detected on thin-layer chromatogram. After treating the reaction mixture as in Example 2, isocoformycin (21 mg, 20%) was obtained.

Workup

  1. additionAfter treating the reaction mixture as in Example 2

Sources & evidence

ORD record
ord-f65a7b0e8c6e47c4956a6ad7a8d73e8e
Source dataset
uspto-grants-1979_08
Patent number
US04163839

Reaction notes

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