244642-03-3

Basic information

• Product Name: Thymidine, 3'-azido-3'-deoxy-, 5'-(phenylmethyl phosphonate)
• CAS NO: 244642-03-3
• Molecular Formula: C17H20N5O6P
• Molecular Weight: 421.349
• Mol File: 244642-03-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Thymidine, 3'-azido-3'-deoxy-, 5'-(phenylmethyl phosphonate)(CAS DataBase Reference)
• NIST Chemistry Reference: Thymidine, 3'-azido-3'-deoxy-, 5'-(phenylmethyl phosphonate)(244642-03-3)
• EPA Substance Registry System: Thymidine, 3'-azido-3'-deoxy-, 5'-(phenylmethyl phosphonate)(244642-03-3)

Safety Data

• Hazardous Substances Data: 244642-03-3(Hazardous Substances Data)

Upstream product

• 322684-67-3 C₂₀H₂₈N₅O₆P 
• 329237-23-2 O-cyclohexyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate 
• 322684-86-6 C₂₀H₂₇N₂O₆P 
• 376356-94-4 C₁₅H₂₄N₅O₆P 
• 322684-70-8 P-(tert-butyl)-3'-azido-3'-deoxythymidine 5'-hydrogenphosphonate 
• 329237-18-5 ((2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isopropyl phosphonate 
• 158689-24-8 O-ethyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate 
• 158689-23-7 C₁₁H₁₆N₅O₆P 
• 124930-59-2 3'-azido-3'-deoxythymidin-5'-yl H-phosphonate monoester 
• 3056-17-5 stavudin 
• 29706-85-2 3'-azido-2',3'-dideoxythymidine monophosphate 
• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 329237-23-2 O-cyclohexyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate 
• 124930-59-2 3'-azido-3'-deoxythymidin-5'-yl H-phosphonate monoester 
• 30516-87-1 3'-azido-2',3'-deoxythymidine 

Relevant articles and documents

Synthesis of AZT/d4T boranophosphates as anti-HIV prodrug candidates

AZT/d4T phosphonates were synthesized by sequential condensation of AZT/ d4T with the corresponding alcohols or 5′-DMT-thymidine in the presence of pivaloyl chloride. Sequential silylation, boronation, and hydrolysis in ammonium hydroxide of these phosphonates led to anti-HIV prodrug candidates AZT/d4T boranophosphates.

P-(Alkyl)-nucleoside 5′-hydrogenphosphonates as depot forms of antiviral nucleotide analogues

P-(Alkyl)esters of AZT 5′-hydrogenphosphonate were synthesized and their stabilities in the phosphate buffer and human serum were evaluated. The esters bearing residues of primary and secondary alcohols were degraded to give AZT, whereas those containing tertiary alkyl groups yielded AZT 5′-hydrogenphosphonate. The corresponding derivatives of d2A and d2T showed the same properties.