2'-O-ACETYL-5'-O-BENZOYL-3'-DEOXY-5-METHYLURIDINE

Base Information

• Chemical Name: 2'-O-ACETYL-5'-O-BENZOYL-3'-DEOXY-5-METHYLURIDINE
• CAS No.: 143653-60-5
• Molecular Formula: C19H20N2O7
• Molecular Weight: 388.377
• Mol file: 143653-60-5.mol

Synonyms:2'-O-ACETYL-5'-O-BENZOYL-5-METHYL-3'-DEOXYURIDINE;

Chemical Property of 2'-O-ACETYL-5'-O-BENZOYL-3'-DEOXY-5-METHYLURIDINE

Chemical Property:

• PSA: 116.69000
• LogP: 0.92120

Purity/Quality:

97% ^*data from raw suppliers

2''-O-Acetyl-5''-O-benzoyl-5-methyl-3''-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2''-O-Acetyl-5''-O-benzoyl-5-methyl-3''-deoxyuridine can be used in therapeutic use and biological study of deoxyribonucleosides and derivatives as anti-amoebic agents.

Technology Process of 2'-O-ACETYL-5'-O-BENZOYL-3'-DEOXY-5-METHYLURIDINE

There total 7 articles about 2'-O-ACETYL-5'-O-BENZOYL-3'-DEOXY-5-METHYLURIDINE 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: 93.0%

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → 2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine (143653-60-5)

Guidance literature:

With tin(IV) chloride; In acetonitrile;

DOI:10.1016/S0040-4039(00)74670-3

Reference yield: 33.0%

1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)-5-methyluracil (188754-55-4) → 2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine (143653-60-5)

Guidance literature:

With magnesium(II) perchlorate; 3,6,9-trimethyl-9H-carbazole; In water; isopropyl alcohol; Photolysis;

DOI:10.1021/jo0003652

Reference yield:

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → 2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine (143653-60-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 10 h / 20 °C

2: 94 percent / SnCl₄ / acetonitrile / 20 °C

3: 33 percent / 3,6-dimethyl-9-methylcarbazole; Mg(ClO₄)2 / propan-2-ol; H₂O / Photolysis

With 2,6-dimethylpyridine; magnesium(II) perchlorate; tin(IV) chloride; 3,6,9-trimethyl-9H-carbazole; In dichloromethane; water; isopropyl alcohol; acetonitrile; 1: Acylation / 2: Substitution / 3: Elimination;

DOI:10.1021/jo0003652

upstream raw materials:

5-Methyl-1-trimethylsilanyl-1H-pyrimidine-2,4-dione

(2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

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

Downstream raw materials:

3'-deoxy-5'-O-dimethoxytrityl-5-methyluridine

Diisopropyl-phosphoramidous acid (2R,3R,5S)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Refernces

• 1、 Kumar,Khan,Manglani,Khan,Katti. "Synthesis and antifungal activity of 3'-deoxyribonucleosides". . p. 1049 - 1058. Retrieved 2007/10/02.