3'-azido-3'-deoxyarabinothymidine

Base Information

• Chemical Name: 3'-azido-3'-deoxyarabinothymidine
• CAS No.: 99614-77-4
• Molecular Formula: C₁₀H₁₃N₅O₅
• Molecular Weight: 283.244
• Mol file: 99614-77-4.mol

Synonyms:1-((2R,3S,4S,5S)-4-Azido-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione;3'-azido-3'-deoxythymidine;

Chemical Property of 3'-azido-3'-deoxyarabinothymidine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 154.30000
• Density: g/cm³
• LogP: -1.77274

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-azido-3'-deoxyarabinothymidine

There total 12 articles about 3'-azido-3'-deoxyarabinothymidine 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: 78.6%

1-(3-azido-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine (128269-50-1) → 3'-azido-3'-deoxythymidine (99614-77-4)

Guidance literature:

With acetic acid; at 90 ℃; for 0.416667h;

DOI:10.1002/ejoc.200300177

Reference yield:

1-{(2R,3S,4S,5S)-4-Azido-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (114551-13-2) → 3'-azido-3'-deoxythymidine (99614-77-4)

Guidance literature:

With acetic acid; at 22 ℃; for 0.5h; Yield given;

DOI:10.1021/jm00402a038

Reference yield:

1-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (138239-62-0) → 3'-azido-3'-deoxythymidine (99614-77-4)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / 1) ice-bath, 15 min; 2) 20 deg C, 3 h

2: aq. NaOH / ethanol / 1 h / 60 °C

3: NaN₃, water / acetone / 20 h / Heating

4: aq. AcOH / 0.5 h / 22 °C

With pyridine; sodium hydroxide; sodium azide; water; acetic acid; In ethanol; dichloromethane; acetone;

DOI:10.1021/jm00402a038

upstream raw materials:

1-{(2R,3S,4S,5S)-4-Azido-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

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

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

thymin