3'-Azido-3'-deoxy-5-Methyuridine

Base Information

• Chemical Name: 3'-Azido-3'-deoxy-5-Methyuridine
• CAS No.: 215176-58-2
• Molecular Formula: C10H13N5O5
• Molecular Weight: 283.244
• Mol file: 215176-58-2.mol

Synonyms:1-((2R,3R,4S,5S)-4-Azido-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione;1-(3-azido-3-deoxy-β-D-ribofuranosyl)thymine;1-(3'-azido-3'-deoxy-β-D-ribofuranosyl)thymine;AZT;3'-azido-3'-deoxy-5-methyluridine;3'-azido-3'-deoxythymidine;3'-azido-3'-deoxy-β-ribosylthimine;

Chemical Property of 3'-Azido-3'-deoxy-5-Methyuridine

Chemical Property:

• PSA: 154.30000
• LogP: -1.77274

Purity/Quality:

97% ^*data from raw suppliers

2α-HydroxyZidovudine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2α-Hydroxy Zidovudine is a metabolite of Zidovudine (A825000); a potent and selective inhibitor of HIV-1 replication.

Technology Process of 3'-Azido-3'-deoxy-5-Methyuridine

There total 11 articles about 3'-Azido-3'-deoxy-5-Methyuridine 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: 79.0%

3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine (215176-57-1) → 1-(3'-azido-3'-deoxy-β-D-ribofuranosyl)thymine (215176-58-2)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 1h;

DOI:10.1080/15257770.2013.847957

Reference yield:

4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (120042-40-2) → 1-(3'-azido-3'-deoxy-β-D-ribofuranosyl)thymine (215176-58-2)

Guidance literature:

With sodium methylate; In methanol; for 1h;

DOI:10.1002/ejoc.200300177

Reference yield:

3-Azido-3-deoxy-1,2-di-O-acetyl-5-O-(4-methylbenzoyl)-β-D-ribofuranose (75096-64-9) → 1-(3'-azido-3'-deoxy-β-D-ribofuranosyl)thymine (215176-58-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: chlorotrimethylsilane; pyridine / various solvent(s) / Heating

1.2: trimethylsilil trifluoromethanesulfonate / 1,2-dichloro-ethane / 5 h

2.1: 1.52 g / NaOCH₃ / methanol / 1 h

With pyridine; chloro-trimethyl-silane; sodium methylate; In methanol;

DOI:10.1002/ejoc.200300177

upstream raw materials:

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

3-Azido-3-deoxy-1,2-di-O-acetyl-5-O-(4-methylbenzoyl)-β-D-ribofuranose

thymin

Downstream raw materials:

1-(3-azido-3-deoxy-5-O-trityl-β-D-ribofuranosyl)thymine

3'-deoxy-3'-(4-phenyl-1,2,3-triazol-1-yl)-5-methyluridine

O-2,2'-anhydro-1-(3-azido-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine

3'-azido-3'-deoxythymidine