117626-99-0

Basic information

• Product Name: 3'-acetate-2'-deoxy-5-ethynyl-uridine
• Synonyms: 3'-acetate-2'-deoxy-5-ethynyl-uridine
• CAS NO: 117626-99-0
• Molecular Formula: C13H14N2O6
• Molecular Weight: 294.26006
• Mol File: 117626-99-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3'-acetate-2'-deoxy-5-ethynyl-uridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-acetate-2'-deoxy-5-ethynyl-uridine(117626-99-0)
• EPA Substance Registry System: 3'-acetate-2'-deoxy-5-ethynyl-uridine(117626-99-0)

Safety Data

• Hazardous Substances Data: 117626-99-0(Hazardous Substances Data)

Upstream product

• 134218-81-8 5’-O-(tert-butyldimethylsilyl)-2’-deoxy-5-iodouridine 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 144872-52-6 1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidine-2,4-(1H,3H)dione 
• 117626-97-8 5'-O-(4,4'-dimethoxytrityl)-5-(1-phenyl-1H-1,2,3-triazol-4-yl)-2'-deoxyuridine 
• 117626-98-9 3'-Acetyl-2'-deoxy-5-ethynyl-5'-(4,4'-dimethoxytrityl)uridine 

Downstream Products

• 61135-33-9 2'-deoxy-5-ethynyluridine 
• 55520-67-7 5-vinyl-2'-deoxyuridine 
• 117627-05-1 5'-O-<(Carboxymethyl)hydroxyphosphinyl>-2'-deoxy-5-ethynyluridine Disodium Salt 
• 117626-80-9 Sodium; {[(2R,3S,5R)-5-(2,4-dioxo-5-vinyl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-acetate 
• 117626-97-8 5'-O-(4,4'-dimethoxytrityl)-5-(1-phenyl-1H-1,2,3-triazol-4-yl)-2'-deoxyuridine 
• 287980-23-8 5-vinyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine 

Relevant articles and documents

New synthetic route to ethynyl-dUTP: A means to avoid formation of acetyl and chloro vinyl base-modified triphosphates that could poison SELEX experiments

5-Ethynyl-2′-deoxyuridine is a common base-modified nucleoside analogue that has served in various applications including selection experiments for potent aptamers and in biosensing. The synthesis of the corresponding triphosphates involves a mild acidic deprotection step. Herein, we show that this deprotection leads to the formation of other nucleoside analogs which are easily converted to triphosphates. The modified nucleoside triphosphates are excellent substrates for numerous DNA polymerases under both primer extension and PCR conditions and could thus poison selection experiments by blocking sites that need to be further modified. The formation of these nucleoside analogs can be circumvented by application of a new synthetic route that is described herein.

Synthesis and Antiviral Activity of Phosphonoacetic and Phosphonoformic Acid Esters of 5-Bromo-2'-deoxyuridine and Related Pyrimidine Nucleosides and Acyclonucleosides

Phosphonoacetic acid (PAA, 1) was coupled with various acyclonucleosides, 2'-deoxyuridines, cytidines, and arabinosyluracils, with 2,4,6-triisopropylbenzenesulfonyl chloride (TPS) or dicyclohexylcarbodiimide (DCCI) as condensing agents, to give a range of phosphonate esters.The carboxylic ester linkage of PAA to the 5'-position of 5-bromo-2'-deoxyuridine (BUdR, 3) was achieved via the mixed anhydride formed from (diethylphosphono)acetic acid and trifluoroacetic anhydride.Phosphonoformic acid (PFA, 2) was coupled with BUdR by using the DCCI method to give the phosphonate ester (59).Of these compounds only phosphonate esters in the 2'-deoxyuridine series showed significant activity against herpes simplex virus types 1 and 2.The BUdR-PAA derivative (7) and the BUdR-PFA derivative (59) were highly active, especially the latter, which was more active than the parent nucleoside BUdR (3) against the type 2 virus.The active compounds may exert their effects by extracellular or intracellular hydrolysis to the corresponding antiviral agents, but an intrinsic component of antiviral activity may also be involved.