1-(2,3,5-Tri-O-benzoyl-beta-L-ribofuranosyl)-N4-acetylcytosine → 4-Amino-1-((2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

HRID 744165Notes

Reaction equation

HRID 744165 reaction equation
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[CH:44]=[CH:43][C:38]([NH:39]C(=O)C)=[N:37][C:35]1=[O:36])(=O)C1C=CC=CC=1>N.CO>[C@H:11]1([N:34]2[CH:44]=[CH:43][C:38]([NH2:39])=[N:37][C:35]2=[O:36])[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@@H:10]1[OH:9]

Participants

3

Reactant 1

HCID 540996081-(2,3,5-Tri-O-benzoyl-beta-L-ribofuranosyl)-N4-acetylcytosine

Product 1

HCID 1229484-Amino-1-((2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-oneYield 52.1%

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

Compound 7 (0.85 g, 1.42 mmol) in NH3 /MeOH (100 ml) was stirred at room temperature overnight and worked up as in Example 1, Step C to give pure 8 (0.18 g, 52%) as white crystals: m.p. 210° C.

Sources & evidence

ORD record
ord-375d007403f44efe9c9510880103b903
Source dataset
uspto-grants-1996_09
Patent number
US05559101

Reaction notes

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