99631-18-2

Basic information

• Product Name: 2,2'-Anhydro-1-(5'-O-Benzoyl-3'-O-methylsulfonyl-β-D-arabinofuranosyl)thymine
• Synonyms: 2,2'-Anhydro-1-(5'-O-Benzoyl-3'-O-methylsulfonyl-β-D-arabinofuranosyl)thymine
• CAS NO: 99631-18-2
• Molecular Weight: 422.416
• Mol File: 99631-18-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2,2'-Anhydro-1-(5'-O-Benzoyl-3'-O-methylsulfonyl-β-D-arabinofuranosyl)thymine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Anhydro-1-(5'-O-Benzoyl-3'-O-methylsulfonyl-β-D-arabinofuranosyl)thymine(99631-18-2)
• EPA Substance Registry System: 2,2'-Anhydro-1-(5'-O-Benzoyl-3'-O-methylsulfonyl-β-D-arabinofuranosyl)thymine(99631-18-2)

Safety Data

• Hazardous Substances Data: 99631-18-2(Hazardous Substances Data)

Upstream product

• 582-25-2 Potassium benzoate 
• 99614-96-7 2′,3′,5′-tris(methanesulfonyl)-5-methyluridine 
• 120649-55-0 1-(5-O-benzoyl-β-D-ribofuranosyl)thymine 
• 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

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

Relevant articles and documents

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.

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.