Sodium methanolate methanol → 4-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidin-2(1H)-one
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([CH:8]2[C:12]([O:14]C(=O)C3C=CC=CC=3)([CH3:13])[CH:11]([O:23]C(=O)C3C=CC=CC=3)[CH:10]([CH2:32][O:33]C(=O)C3C=CC=CC=3)[O:9]2)[C:4](=[O:42])[N:3]=1.C[O-].[Na+].CO>>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([CH:8]2[C:12]([OH:14])([CH3:13])[CH:11]([OH:23])[CH:10]([CH2:32][OH:33])[O:9]2)[C:4](=[O:42])[N:3]=1Participants
3
Procedure
In one synthesis method, depicted in FIG. 5, the synthesis comprises reacting cytosine, BSA and SnCl4/acetonitrile with 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose (FIG. 5, compound 1) to form 4-amino-1-(3,4-dibenzoyloxy-5-benzoyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one (FIG. 5, compound 2); and reacting (FIG. 5, compound 2) with NaOMe/MeOH to provide 4-amino-1-(3,4-dihydroxy-5-hydroxymethyl-3-methyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one (FIG. 5, compound 3), also known as 2-C-methyl-β-D-ribofuranose. The use of cytosine as a starting material rather than benzoyl-cytosine improves the “atom economy” of the process and simplifies purification at later steps.
Sources & evidence
- ORD record
- ord-4880bdd9e7984622a0e95d7b92bff655
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625875B2
Reaction notes
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