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DOI: 10.1055/s-2003-45000
Efficient Preparation of 2-Deoxy-3,5-di-O-p-toluoyl-α-d-ribofuranosyl Chloride
Publication History
Publication Date:
18 December 2003 (online)
Abstract
An efficient method for the synthesis of 1-O-methyl-3,5-di-O-p-toluoyl-2-deoxy-α/β-d-ribose is described. Upon treatment with HCl, 2-deoxy-3,5-di-O-p-toluoyl-α-d-ribofuranosyl chloride, previously unstable, was produced as a white solid, stable in air indefinitely.
Key words
1-O-methyl-3,5-di-O-p-toluoyl-2-deoxy-α/β-d-ribose - 2-deoxy-3,5-di-O-p-toluoyl-α-d-ribofuranosyl chloride - 1-O-methyl-2-deoxy-α/β-d-ribose - hydrogen chloride - p-toluic anhydride
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References
Dhimitruka, I.; SantaLucia, J. Jr., manuscript in preparation.
12p-Toluic anhydride was prepared as follows: p-Toluoyl chloride (1 equiv), water (0.5 equiv) and Et3N (1 equiv) were dissolved in acetone (0.03 mol/30 mL). The solution was stirred for 2 h then filtered. Et3N·HCl at 0 °C was washed with acetone (30 m L) and the combined acetone solutions evaporated to afford the product.