1-[(2R,5S)-5-azido-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-[(2R,5S)-5-azido-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS No.: 140226-08-0
• Molecular Formula: C10H11N5O4
• Molecular Weight: 265.2254
• Mol file: 140226-08-0.mol

Synonyms:

Chemical Property of 1-[(2R,5S)-5-azido-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-[(2R,5S)-5-azido-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

There total 9 articles about 1-[(2R,5S)-5-azido-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione 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:

1-[(2R,5S)-5-Azido-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,5-dihydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione → 1-(4-azido-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine (140226-08-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h; Yield given; Ambient temperature;

DOI:10.1021/jm00086a013

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) → 1-(4-azido-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine (140226-08-0)

Guidance literature:

Multi-step reaction with 8 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

5: 84 percent / imidazole / dimethylformamide / 1 h / 37 °C

6: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

7: lithium benzoate / dimethylformamide / 5.5 h / Ambient temperature

8: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; sodium azide; tetrabutyl ammonium fluoride; water; sodium methylate; lithium benzoate; Iodine monochloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00086a013

Reference yield:

4'-azido-5'-O-(tert-butyldimethylsilyl)thymidine (140226-07-9) → 1-(4-azido-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine (140226-08-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

2: lithium benzoate / dimethylformamide / 5.5 h / Ambient temperature

3: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; tetrabutyl ammonium fluoride; lithium benzoate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00086a013

upstream raw materials:

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

4'-azido-5'-O-(tert-butyldimethylsilyl)thymidine

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

4'-azidothymidine