Uridine → Ribavirin

HRID 1769936Notes

Reaction equation

HRID 1769936 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([NH2:8])=[O:7])=[N:2]1.N1C=CN=N1.[C@@H:14]1(N2C=CC(=O)NC2=O)[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]1[OH:16].[C@@H]1(N2C3N=CN=C(O)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.[C@@H]1(N2C=CC(N)=NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.[C@@H]1(N2C3N=C(N)NC(=O)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.P([O-])(O)(O)=O.[K+]>>[CH:5]1[N:1]([C@@H:14]2[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]2[OH:16])[N:2]=[C:3]([C:6]([NH2:8])=[O:7])[N:4]=1

Participants

9

Reactant 8

HCID 6029UridineHCID 6175CytidineHCID 60961AdenosineHCID 516951Monobasic potassium phosphateHCID 135398635GuanosineHCID 178418936HCID 178418936, compoundHCID 178513825HCID 178513825, compoundHCID 178521066(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxypurin-9-yl)oxolane-3,4-diol

Product 1

HCID 37542Ribavirin

Procedure

By using a substrate solution (pH 6.0) containing 40 mM 1,2,4-triazole-3-carboxamide (hereinafter called "triazole") as the base donor, 40 mM uridine, inosine, cytidine, adenosine or guanosine as the saccharide residue donor and 40 mM potassium dihydrogenphosphate, ribavirin was produced in the same manner as in Example 1. The results are shown in Table 7.

Sources & evidence

ORD record
ord-1e09a9e199bc4a8781d7a3f227cfef63
Source dataset
uspto-grants-1995_01
Patent number
US05384251

Reaction notes

Loading…