4'-azidothymidine

Base Information

• Chemical Name: 4'-azidothymidine
• CAS No.: 130108-72-4
• Molecular Formula: C10H13 N5 O5
• Molecular Weight: 0
• Mol file: 130108-72-4.mol

Synonyms:4'-Azidothymidine

Chemical Property of 4'-azidothymidine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 154.30000
• Density: g/cm³
• LogP: -1.42354

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4'-azidothymidine

There total 6 articles about 4'-azidothymidine 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%

(2R,3S,5R)-2-azido-2-((benzoyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate (1612885-59-2) → 4'-azidothymidine (130108-72-4)

Guidance literature:

With ammonia; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1039/c4md00039k

Reference yield:

1-((2R,4S,5S)-4-hydroxy-5-(iodomethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (25953-14-4,94892-66-7) → 4'-azidothymidine (130108-72-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / sodium methoxide / methanol / 16 h / Heating

2: iodine monochloride, sodium azide / dimethylformamide / 1 h / Ambient temperature

3: 95 percent / pyridine / 16 h / Ambient temperature

4: 1.) m-chloroperbenzoic acid, water, 2.) sodium methoxide / 1.) dichloromethane, RT, 3.5 h, 2.) methanol, RT, 30 min

With pyridine; sodium azide; water; sodium methylate; Iodine monochloride; 3-chloro-benzenecarboperoxoic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00086a013

Reference yield:

1-((2R,4S)-4-hydroxy-5-methylenetetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (28034-72-2) → 4'-azidothymidine (130108-72-4)

Guidance literature:

Multi-step reaction with 3 steps

1: iodine monochloride, sodium azide / dimethylformamide / 1 h / Ambient temperature

2: 95 percent / pyridine / 16 h / Ambient temperature

3: 1.) m-chloroperbenzoic acid, water, 2.) sodium methoxide / 1.) dichloromethane, RT, 3.5 h, 2.) methanol, RT, 30 min

With pyridine; sodium azide; water; sodium methylate; Iodine monochloride; 3-chloro-benzenecarboperoxoic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm00086a013

upstream raw materials:

4'-azido-5'-deoxy-5'-iodo-3'-O-(4-methoxybenzoyl)thymidine

1-((2R,4S,5S)-4-hydroxy-5-(iodomethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

1-((2R,4S,5S)-5-azido-4-hydroxy-5-(iodomethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

1-((2R,4S)-4-hydroxy-5-methylenetetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Downstream raw materials:

1-(4-azido-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine

N-(4-(1-((2R,3S,5R)-3-hydroxy-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)-1H-1,2,3-triazol-4-yl)phenyl)acetamide

1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-5-(4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

1-((2R,4S,5R)-5-(4-cyclohexyl-1H-1,2,3-triazol-1-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Refernces

• 1、 Maag,Rydzewski,McRoberts,Crawford-Ruth,Verheyden,Prisbe. "Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides". . p. 1440 - 1451. Retrieved 2007/10/02.