2',3'-Dideoxyuridine

Base Information

• Chemical Name: 2',3'-Dideoxyuridine
• CAS No.: 5983-09-5
• Molecular Formula: C9H12 N2 O4
• Molecular Weight: 212.205
• Hs Code.: 2934999090
• Mol file: 5983-09-5.mol

Synonyms:2',3'-Dideoxyuridine;d2U

Chemical Property of 2',3'-Dideoxyuridine

Chemical Property:

• Melting Point: 127-129 °C(lit.)
• PKA: 9.39±0.10(Predicted)
• PSA: 84.32000
• Density: 1.397g/cm3
• LogP: -0.79350
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

2’,3’-Dideoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 22-24/25-45-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: 2',3'-Dideoxyuridine (ddU or d2U) is a nucleoside analog investigated for its potential anti-HIV activity. While it exhibits limited efficacy due to inefficient phosphorylation by thymidine kinase, its phosphoramidate ‘ProTide’ derivatives show improved membrane permeability and moderate anti-HIV activity, suggesting that bypassing the initial phosphorylation barrier can enhance its therapeutic potential. However, the underlying metabolic limitations of ddU itself remain a challenge for its antiviral application.

Technology Process of 2',3'-Dideoxyuridine

There total 50 articles about 2',3'-Dideoxyuridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1'-[5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-glycero-pentofuranosyl]uracil → 2',3'-Dideoxyuridine (5983-09-5,153547-98-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/j.chembiol.2019.04.010

Reference yield: 97.0%

2',3'-dideoxy-2',3'-didehydrouridine (5974-93-6) → 2',3'-Dideoxyuridine (5983-09-5,153547-98-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 1h;

DOI:10.1021/jo00256a056

Reference yield: 94.0%

2`,3`-dideoxycytidine (7481-89-2) → 2',3'-Dideoxyuridine (5983-09-5,153547-98-9)

Guidance literature:

With Tris-HCl buffer; at 50 ℃; for 3.5h; pH=7.25;

DOI:10.1007/s10600-006-0080-z

upstream raw materials:

1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-4-methoxypyrimidin-2(1H)-one

1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>uracil

2',3'-dideoxy-2',3'-didehydrouridine

1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)uracil

Downstream raw materials:

1-C-(purin-N⁹-yl)-1,2,3-dideoxy-β-D-erythro-furanose

6-bromo-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine

6-iodo-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine

2-amino-6-bromo-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine

Refernces

An investigation into the anti-HIV activity of 2′,3′-didehydro- 2′,3′-dideoxyuridine (d4U) and 2′,3′-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives

10.1039/b904276h

The study investigates the anti-HIV activity of 2',3'-didehydro-2',3'-dideoxyuridine (d4U) and 2',3'-dideoxyuridine (ddU) and their phosphoramidate ‘ProTide’ derivatives. The researchers hypothesize that the poor anti-HIV activity of d4U and ddU might be due to inefficient phosphorylation by thymidine kinase. Molecular modeling shows that both d4U and ddU have unfavorable positions at the active site of thymidine kinase, which likely hampers their first phosphorylation step. To bypass this issue, the ‘ProTide’ approach was applied, where the phosphate group is masked to improve membrane permeability and reduce susceptibility to dephosphorylation. The study found that while the ‘ProTide’ approach turned ddU into a moderately active anti-HIV agent, it did not enhance the activity of d4U. Enzymatic assays revealed that d4U phosphoramidates were metabolized to release d4U monophosphate, suggesting that poor second and/or third phosphorylation steps are the likely reasons for d4U's lack of anti-HIV activity.