165047-01-8

Basic information

• Product Name: URIDINE, 2'-BROMO-2'-DEOXY-5-METHYL-, 5'-BENZOATE 3'-METHANESULFONATE
• Synonyms: URIDINE, 2'-BROMO-2'-DEOXY-5-METHYL-, 5'-BENZOATE 3'-METHANESULFONATE;5'-BENZOYL-3-ETHANESULFONYL-2-BROMOTHYMIDINE;5-BENZOYL-3ETHANESULFONYL-2ROMOTHYMIDINE;5-BENZOYL-3-Methanesulfonyl-2-Bromothymidine
• CAS NO: 165047-01-8
• Molecular Formula: C₁₈H₁₉BrN₂O₈S
• Molecular Weight: 503.32
• Mol File: 165047-01-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: URIDINE, 2'-BROMO-2'-DEOXY-5-METHYL-, 5'-BENZOATE 3'-METHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: URIDINE, 2'-BROMO-2'-DEOXY-5-METHYL-, 5'-BENZOATE 3'-METHANESULFONATE(165047-01-8)
• EPA Substance Registry System: URIDINE, 2'-BROMO-2'-DEOXY-5-METHYL-, 5'-BENZOATE 3'-METHANESULFONATE(165047-01-8)

Safety Data

• Hazardous Substances Data: 165047-01-8(Hazardous Substances Data)

Usage

General Description

URIDINE, 2'-BROMO-2'-DEOXY-5-METHYL-, 5'-BENZOATE, 3'-METHANESULFONATE is a complex chemical compound that is composed of uridine, 2'-bromo-2'-deoxy-5-methyl, 5'-benzoate, and 3'-methanesulfonate. Uridine is a nucleoside that plays a crucial role in the formation of RNA. The 2'-bromo-2'-deoxy-5-methyl compound is a derivative of nucleosides and has potential antiviral properties. The 5'-benzoate group is a benzoic acid derivative, and the 3'-methanesulfonate is a methylsulfonyl group, both of which can have various chemical and biological activities. The combination of these compounds could potentially have applications in pharmaceuticals, biochemistry, and molecular biology.

Upstream product

• 532-32-1 sodium benzoate 
• 99631-18-2 2,2'-Anhydro-1-(5'-O-Benzoyl-3'-O-methylsulfonyl-β-D-arabinofuranosyl)thymine 
• 1463-10-1 5-Methyluridine 
• 99614-96-7 2′,3′,5′-tris(methanesulfonyl)-5-methyluridine 

Downstream Products

• 3056-17-5 stavudin 
• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 106060-78-0 3'-azido-5'-O-benzoyl-3'-deoxythymidine 
• 165047-02-9 ((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(methylsulfonyloxy)-tetrahydrofuran-2-yl)methyl benzoate 
• 70838-44-7 2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine 
• 122567-97-9 5′-benzoyl-2′,3′-didehydro-3′-deoxythymidine 

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.