99631-18-2

Upstream product

• 120649-55-0 1-(5-O-benzoyl-β-D-ribofuranosyl)thymine 
• 99614-96-7 2′,3′,5′-tris(methanesulfonyl)-5-methyluridine 
• 582-25-2 Potassium benzoate 
• 3180-76-5 2',3',5'-tri-O-benzoyluridine 
• 1463-10-1 5-Methyluridine 
• 532-32-1 sodium benzoate 
• 120673-67-8 1-<5-O-Benzoyl-2,3-O-bis(methylsulfonyl)-β-D-ribofuranosyl>thymine 

Downstream Products

• 115913-83-2 3'-cyano-3'-deoxy-β-D-arabinofuranosylthymine 
• 14486-22-7 1-(2,3-anhydro-β-D-lyxofuranosyl)thymine 
• 3056-17-5 stavudin 
• 122567-97-9 5′-benzoyl-2′,3′-didehydro-3′-deoxythymidine 
• 165047-01-8 5′-benzoyl-3′α-methanesulfonyl-2′α-bromothymidine 

Relevant academic research and scientific papers

Multistep Continuous Flow Synthesis of Stavudine

Herein, we demonstrate an elegant multistep continuous flow synthesis for stavudine (d4T), a potent nucleoside chemotherapeutic agent for human immunodeficiency virus, acquired immunodeficiency syndrome (AIDS) and AIDS-related conditions. This was accomplished via six chemical transformations in five sequential continuous flow reactors from an affordable starting material, 5-methyluridine. In the first instance, single step continuous flow synthesis was demonstrated with an average of 97% yield, 21.4 g/h throughput per step, and a total of 15.5 min residence time. Finally, multistep continuous flow synthesis of d4T in 87% total yield with a total residence time of 19.9 min and 117 mg/h throughput without intermediate purification was demonstrated.

Independent synthesis and fate studies of impurities in process intermediates of the anti-AIDS drug d4T

Impurities in isolated intermediates in a process to prepare d4T were identified, independently synthesized, and then taken through the process to determine their ultimate fate. Some of the products from these fate studies were also independently synthesized and used in the validation of impurity assay methods.

5'-Benzoyl-2'α'-bromo-3'-O-methanesulfonylthymidine: A Superior Nucleoside for the Synthesis of the Anti-Aids Drug D4T (Stavudine).

The anti-AIDS drug d4T is prepared in 75percent overall yiled starting from the readily available ribonucleoside 5-methyluridine (1).The key step in this new synthesis is the zinc-induced reductive elimination of the bromomesylate 4, which affords d4T without nucleoside bond cleavage.A facile procedure for the deprotection/isolation of this highly water soluble product is also described.