198974-91-3

Upstream product

• 102-09-0 bis(phenyl) carbonate 
• 22423-26-3 O-2,2'-cyclo-5-methyluridine 
• 144-55-8 sodium hydrogencarbonate 

Downstream Products

• 16053-52-4 threothymidine 
• 30516-87-1 Zidovudine 
• 22423-26-3 O-2,2'-cyclo-5-methyluridine 

Relevant academic research and scientific papers

A process for the preparation of beta-thymidine

The invention provides a process for the preparation of beta-thymidine of the formula wherein Me represents methyl groups, which comprises: (a) preparing the deprotected xylothymidine of the formula by removing by conventional method, the acyl group from 1,2,3-tri-O-acyl-xylothymidine of the formula wherein R1 represents acetyl group, R2 represents benzoyl or acetyl group and Me represents methyl group, (b) condensing the deprotected xylothymidine of the formula with dialkyl or diaryl carbonate in the presence of a base and an organic solvent to yield 2,2'-anhydrothymidine of the formula wherein Me represents methyl group, (c) brominating the 2,2'-anhydrothymidine of the formula as defined above by conventional method to afford 2'-bromo derivative of the formula wherein R represents hydrogen of acetyl group, Br represents bromine and Me represents methyl group, (d) reducing the 2'-bromo derivative of the formula by conventional methods to yield beta-thymidine of the formula or its diacetyl derivative.

Synthesis of beta-thymidine

A process is provided in which a mixture of alpha- and beta-anomers is converted selectively to the desired beta-thymidine. The process involves the following steps: (a) converting a mixture of alpha- and beta-anomers of tetra-O-acylribofuranose to tri-O-acyl-β-ribothymidine; (b) converting tri-O-acyl-β-ribothymidine to β-ribothymidine; (c) converting β-ribothymidine to 2,2'-anhydro-β-thymidine; (d) converting 2,2'-anhydro-β-thymidine to 2'-halo-2'-deoxy-5-methyluridine; and (e) converting 2'-halo-2'-deoxy-5-methyluridine to beta-thymidine. The mixture of alpha- and beta-anomers of tetra-O-acylribofuranose may be produced by any suitable procedure such as by converting lower alkyl ribofuranoside to the tetra-O-acylribofuranose mixture. The lower alkyl ribofuranosides may in turn be produced by various methods. However, a desirable way of effecting this conversion involves use of D-ribose as the starting material which is converted to the lower alkyl ribofuranoside.