1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione
• CAS No.: 73971-82-1
• Molecular Formula: C10H13 N5 O4
• Molecular Weight: 267.244
• Mol file: 73971-82-1.mol

Synonyms:1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione

Chemical Property of 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione

Chemical Property:

• PSA: 134.33000
• LogP: -0.33124

Purity/Quality:

97% ^*data from raw suppliers

3''-epi-Azido-3''-deoxythymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3'-ent-Azido-3'-deoxythymidine is the 3’-enantiomer of 3'-Azido-3'-deoxythymidine (A825000), a potent and selective inhibitor of HIV-1 replication.

Technology Process of 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione

There total 11 articles about 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-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: 83.0%

1-(3-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine (66503-47-7) → 1-(3'-azido-2',3'-dideoxy-β-D-threo-pentofuranosyl)thymine (73971-82-1,399024-19-2)

Guidance literature:

With water; acetic acid; at 120 ℃; for 0.333333h;

DOI:10.1002/hlca.200390295

Reference yield: 38.0%

2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) + 4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-1,1-dimethoxy-D-glycero-pentanose (371164-35-1) → 3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2) + 1-(3'-azido-2',3'-dideoxy-β-D-threo-pentofuranosyl)thymine (73971-82-1,399024-19-2) + 1-((2S,4R,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (399024-19-2) + alpha-3'-azido-2',3'-dideoxythymidine (66323-40-8,399024-19-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -30 - 20 ℃; Further byproducts given;

DOI:10.1016/S0040-4020(01)00695-0

Reference yield:

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine (42214-24-4) → 1-(3'-azido-2',3'-dideoxy-β-D-threo-pentofuranosyl)thymine (73971-82-1,399024-19-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / NaN₃ / dimethylformamide / 4 h / 100 °C

2: 83 percent / AcOH; H₂O / 0.33 h / 120 °C

With sodium azide; water; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1002/hlca.200390295

upstream raw materials:

1-(3-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine

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

4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-1,1-dimethoxy-D-glycero-pentanose

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine