Preparation of Thioarabinofuranosyl Compounds and Use Thereof

Secrist, III etal, US Patent 6,576,621 (June 10, 2003) Assignee Southern Research Institute 

Utility Anti-Neoplastic Agent Inhibitor of DNA Replication 

L-Xylose (167 mmol) was stirred 5 hours in 675 ml 0.5% HCl in methyl alcohol at ambient temperature and neutralized with Amberlite IRA-400 OH anion exchange resin. The 

The product from Step 1 (60.9 mmol) dissolved in 350 ml THF was treated with NaH (370 mmol) and then stirred 15 minutes at 0°C. Thereafter, benzyl bromide (214 mmol) and solid NBU4I (0.96 mmol) were added and the mixture stirred 3 days at ambient temperature. It was quenched with 25 ml methyl alcohol, concentrated, purified by chromatography on silica gel with cyclohexane/EtOAc, 9 1, and the product isolated in 87% yield. H-NMR and MS data supplied. 

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