5983-09-5

Basic information

• Product Name: 2',3'-Dideoxyuridine
• Synonyms: BETA-D-2',3'-DIDEOXYURIDINE;DDU;1-(2',3'-DIDEOXY-BETA-RIBOFURANOSYL)URACIL;2',3'-DIDEOXYURIDINE;2',3'-Dideoxy-D-uridine;2'', 3''-DIDEOXYURIDINE (DDU);1-[(2S,5R)-5-(hydroxyMethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyriMidine-2,4-dione;2',3'-ddU
• CAS NO: 5983-09-5
• Molecular Formula: C₉H₁₂N₂O₄
• Molecular Weight: 212.2
• EINECS: 2017-001-1
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines
• Mol File: 5983-09-5.mol
• Article Data: 20

Chemical Properties

• Melting Point: 127-129 °C(lit.)
• Appearance: /
• Density: 1.397g/cm3
• Storage Temp.: 2-8°C
• PKA: 9.39±0.10(Predicted)
• BRN: 750592
• CAS DataBase Reference: 2',3'-Dideoxyuridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-Dideoxyuridine(5983-09-5)
• EPA Substance Registry System: 2',3'-Dideoxyuridine(5983-09-5)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 22-24/25-45-36/37/39-27-26
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 5983-09-5(Hazardous Substances Data)

Usage

Chemical Properties

powder

Uses

2’,3’-Dideoxyuridine can be used as prodrug precursors or in antisense oligonucleotide synthesis. Also, it can be used to synthesize ProTide derivatives and evaluated against HIV-1 and HIV-2.

Upstream product

• 5974-93-6 2',3'-dideoxy-2',3'-didehydrouridine 
• 7481-89-2 2`,3`-dideoxycytidine 
• 127676-65-7 C₂₀H₁₅NO₅ 
• 58-96-8 uridine 
• 42867-74-3 1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-uracil 
• 16628-81-2 2',3'-O-(methoxymethylidene)uridine 
• 66-22-8 uracil 
• 69655-05-6 didanosine 
• 28616-91-3 Benzoic acid 5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 56-86-0 L-glutamic acid 
• 187458-07-7 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate 
• 142824-48-4 Benzoic acid (2S,5R)-5-cyano-tetrahydro-furan-2-ylmethyl ester 
• 142824-52-0 Benzoic acid (2S,5R)-5-[3-((E)-3-ethoxy-acryloyl)-ureido]-tetrahydro-furan-2-ylmethyl ester 

Downstream Products

• 129151-58-2 N³-<(diethylphosphono)methyl>-2',3'-dideoxyuridine 
• 126502-08-7 1-C-(purin-N⁹-yl)-1,2,3-dideoxy-β-D-erythro-furanose 
• 102935-28-4 5'-O-acetyl-2',3'-dideoxyuridine 
• 28616-93-5 2',3'-dideoxy-5-bromouridine 
• 105784-83-6 2',3'-dideoxy-5-iodouridine 
• 132194-25-3 6-bromo-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine 
• 120503-37-9 6-iodo-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine 
• 132194-22-0 2-amino-6-bromo-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine 
• 122970-35-8 2-amino-6-chloro-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine 
• 132194-27-5 2,6-dichloro-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine 
• 132194-21-9 2-amino-6-fluoro-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)purine 
• 132194-24-2 6-fluoro-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine 
• 132194-23-1 2-amino-6-iodo-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine 
• 139300-66-6 Oxalic acid (2S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 4-nitro-phenyl ester 

Relevant articles and documents

Di-ddU-α-hydroxyphosphonate and α-hydroxy-α-methylphosphonates as potential prodrugs of antiviral nucleoside analogues

The synthesis of a potential new prodrug system for the antiviral nucleoside ddU 1 based on α-hydroxybenzylphosphonates 2 and 3 is described. In principle, 2, 3 are able to hydrolyze via different mechanisms yielding ddU H-phosphonate 4 or ddU monophosphate 5, respectively.

Synthesis and Characterization of Specific Reverse Transcriptase Inhibitors for Mammalian LINE-1 Retrotransposons

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Developing a collection of immobilized nucleoside phosphorylases for the preparation of nucleoside analogues: Enzymatic synthesis of arabinosyladenine and 2',3'-dideoxyinosine

The use of nucleoside phosphorylases (NPs; EC 2.4.2.n) represents a convenient alternative to the chemical route for the synthesis of natural and modified nucleosides. We purified four recombinantly expressed nucleoside phosphorylases from the bacterial pathogens Citrobacter koseri, Clostridium perfringens, and Streptococcus pyogenes (CkPNPI, CkPNPII, CpUP, SpUP) and their substrate specificity was investigated towards either natural pyrimidine or purine nucleosides and some analogues, namely, arabinosyladenine (araA) and 2',3'-dideoxyinosine (ddI). A 2-3 % activity towards these latter compounds (compared to the natural substrates) was observed. Enzyme activities were compared to the specificities obtained for the enzymes pyrimidine nucleoside phosphorylase from Bacillus subtilis (BsPyNP) and purine nucleoside phosphorylase from Aeromonas hydrophila (AhPNPII) previously reported by some of the authors. The enzymes displaying the suitable specificity for the synthesis of araA and ddI were immobilized on aldehyde-agarose. The immobilized preparations were highly stable at alkaline pH and in the presence of methanol or acetonitrile as cosolvent. They were used in the synthesis of araA and ddI by a one-pot, bienzymatic transglycosylation achieving 74 and 44 % conversion, respectively. Something different: Nucleoside phosphorylases are a convenient alternative to the chemical route for the synthesis of natural and modified nucleosides. Four new nucleoside phosphorylases have been prepared, characterized, and tested for their use in biocatalyzed syntheses of araA and ddI (see scheme). A generally applicable immobilization technique has been found to provide active and stable biocatalysts.