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:

98%,99%, ^*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:

• 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.

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:

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-fluoro-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)purine

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

Refernces

• 1、 Banuelos-Sanchez, Guillermo,Franco-Montalban, Francisco,Tamayo, Juan A.. "NMR studies of pyrimidinic nucleosides derived from 2,3-dideoxy-d-ribose with inhibitory activity on LINE-1 mobility". . p. 118 - 125. Retrieved 2019/11/28.
• 2、 Pertenbreiter, Florian,Balzarini, Jan,Meier, Chris. "Nucleoside mono- and diphosphate prodrugs of 2′,3′-dideoxyuridine and 2′,3′-dideoxy-2′,3′-didehydrouridine". . p. 94 - 106. Retrieved 2015/03/13.