ChemicalBook CAS DataBase List Idoxuridine

Idoxuridine synthesis

9synthesis methods

Product Name:Idoxuridine
CAS Number:54-42-2
Molecular formula:C9H11IN2O5
Molecular Weight:354.1

Idoxuridine is mainly used topically to treat herpes simplex keratitis.Idoxuridine can be synthesised by several related ways:

1) The reaction of 5-iodouracil (I) with refluxing POCl3 and dimethylaniline gives 2,4-dichloro-5-iodopyrimidine (II), which by reaction with NaOCH3 in refluxing methanol, is converted into 2,4-dimethoxy-5-iodopyrimidine (III). The reaction of (III) with 2-deoxy-3,6-di-Op-toluoyl-D-ribofuranosyl chloride (IV) in acetonitrile yields the ribofuranosyl pyridone (V ), which is demethylated with acetic anhydride – dry HCl to afford 2′-deoxy-5-iodo-3‘, 6′-di-Op-toluoyluridine (VI) Finally, this compound is hydrolyzed with NaOCH3 in methanol.

3) The iodination of 2′-deoxyuridine (IX) with iodine, iodic acid, acetic anhydride, CCl4 and water gives 2′-deoxy-5,6-diiodo-5,6-dihydrouridine (X), which is then treated with NaOH to eliminate HI.

951-78-0 Synthesis

951-78-0
467 suppliers
$5.00/100mg

696-07-1
291 suppliers
$17.00/5g

54-42-2
438 suppliers
$6.00/250mg

66-22-8 Synthesis

66-22-8
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$5.00/10g

Yield:-

Reaction Conditions:

with thymidine phosphorylase from Escherichia coli (E_.C_. 2.4.2.4) immobilized on Sepabeads EC-EP in aq. phosphate buffer; pH=7.5 at 20; for 3 h;Enzymatic reaction;Reagent/catalyst;

Steps:

2.7. Transglycosylation: general protocol
General procedure: To a solution of phosphate buffer (10 mM) at pH 7.5 (10 mL) containing 2′-deoxyuridine (1, 45.6 mg, 20 mM) and the 5-substituted base (8-13, 13-22 mg, 10 mM), 10 IU of immobilized enzyme (EcTP or BsPyNP) were added and the suspension was kept under mechanical stirring at room temperature. In the case of 5-bromovinyluracil (13), pH was set to 10 by using a 10 mM phosphate buffer containing 13.8 mg of potassium carbonate (final concentration 10 mM). Aliquots (0.2 mL) were periodically withdrawn, filtered through a pipette filter device to remove the biocatalyst and analyzed by HPLC (see below for chromatographic conditions and R_t). When the highest conversion was achieved, the reaction was stopped by filtration of the immobilized biocatalyst on a Büchner funnel with a sintered glass disc under reduced pressure. The produced nucleosides (2 and 14-18) were identified by comparison of their HPLC R_t with that of authentic samples.

References:

Serra, Immacolata;Bavaro, Teodora;Cecchini, Davide A.;Daly, Simona;Albertini, Alessandra M.;Terreni, Marco;Ubiali, Daniela [Journal of Molecular Catalysis B: Enzymatic,2013,vol. 95,p. 16 - 22]

FullText

951-78-0 Synthesis

951-78-0
467 suppliers
$5.00/100mg

54-42-2
438 suppliers
$6.00/250mg

References

1956-30-5 Synthesis