130481-61-7

Basic information

• Product Name: 1-(3-azido-2,3,5-trideoxy-beta-D-erythro-hexofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione
• Synonyms: 2,4(1H,3H)-Pyrimidinedione, 1-(3-azido-2,3,5-trideoxy-.beta.-D-erythro-hexofuranosyl)-5-methyl-; 2,4(1H,3H)-Pyrimidinedione, 1-(3-azido-2,3,5-trideoxy-beta-D-erythro-hexofuranosyl)-5-methyl-
• CAS NO: 130481-61-7
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 281.2679
• Mol File: 130481-61-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-(3-azido-2,3,5-trideoxy-beta-D-erythro-hexofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-azido-2,3,5-trideoxy-beta-D-erythro-hexofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione(130481-61-7)
• EPA Substance Registry System: 1-(3-azido-2,3,5-trideoxy-beta-D-erythro-hexofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione(130481-61-7)

Safety Data

• Hazardous Substances Data: 130481-61-7(Hazardous Substances Data)

Upstream product

• 189194-84-1 5'-deoxy-5'-C-(4,4'-dimethoxytrityloxymethyl)thymidine 
• 22567-03-9 5'-homothymidine 
• 148522-79-6 C₂₅H₃₈N₂O₆Si 
• 1610517-69-5 C₂₅H₃₆N₂O₅Si 
• 142325-10-8 5′-deoxy-5′-C-methenyl-3′-O-(tert-butyldimethylsilyl)thymidine 
• 131118-61-1 3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde 
• 40733-27-5 3'-O-(t-butyldimethylsilyl)thymidine 
• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 
• 50-89-5 thymidine 
• 1610517-71-9 C₃₂H₃₃N₅O₆ 
• 130481-53-7 Benzoic acid (R)-2-((3aR,5R,6R,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-p-tolyloxythiocarbonyloxy-ethyl ester 
• 130481-52-6 Benzoic acid (R)-2-hydroxy-2-((3aR,5R,6R,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester 
• 64993-88-0 1,2-O-isopropylidene-3-O-methanesulfonyl-α-D-allofuranose 
• 14728-80-4 1,2:5,6-di-O-isopropylidene-3-O-(methylsulphonyl)-α-D-allofuranose 

Relevant articles and documents

Phospho-carboxylic anhydride of a homologated nucleoside leads to primer degradation in the presence of a polymerase

Starting from thymidine, through a series of key synthetic transformations (e.g., Wittig reaction, hydroboration, Mitsunobu reaction and TEMPO oxidation) a nucleoside homologue bearing a phospho-carboxylic anhydride group at 6′ position was synthesized. The potential of polymerases to catalyze amide bond formation was investigated by using a modified primer with an amino group at 3′ position and the synthesized phosphoanhydro compound as substrate. Unfortunately, we did not observe the desired product either by gel electrophoresis or mass spectrometry. In contrast, the instability of the phosphoanhydro compound could lead to pyrophosphate formation and thus, to pyrophosphorolysis of the primer rather than to primer extension.

Side-Chain Derivatives of Biologically Active Nucleosides. 1. Side-Chain Analogs of 3'-Azido-3'-deoxythymidine (AZT)

Starting from 3-O-mesyl-1,2-O-isopropylidene-α-D-allofuranose (9) the anomeric mixtures of the requisite carbohydrates 1,2-di-O-acetyl-6-O-benzoyl-5-deoxy-3-O-mesyl-D-allofuranoses 17Aα/β, 1,2-di-O-acetyl-5,6-di-O-benzoyl-3-O-mesyl-D-allofuranoses 17Bα/β,

1-(3′- Azido-2′, 3′, 5′ - trideoxy- β - d . Allofuranosyl) thymine a side-chain homologue of 3′- azido - 3′-deoxythymidine

1-(3′-Azido-2′,3′,5′-trideoxy-β-D- allofuranosyl)thymine 12 (homo-AZT) was synthesized starting from 1,2;5,6-di-O-isopropylidene- 3-O-mesyl-α-D-allofuranose 1 in an eleven step sequence (overall yield: 4%).