1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-5'-(tert-butyldiphenylsilyl)-3'-deoxy-β-ribofuranosyl}uracil

Base Information

• Chemical Name: 1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-5'-(tert-butyldiphenylsilyl)-3'-deoxy-β-ribofuranosyl}uracil
• CAS No.: 183374-92-7
• Molecular Formula: C₄₀H₄₀N₂O₈Si
• Molecular Weight: 704.852
• Mol file: 183374-92-7.mol

Synonyms:1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-5'-(tert-butyldiphenylsilyl)-3'-deoxy-β-ribofuranosyl}uracil

Chemical Property of 1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-5'-(tert-butyldiphenylsilyl)-3'-deoxy-β-ribofuranosyl}uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-5'-(tert-butyldiphenylsilyl)-3'-deoxy-β-ribofuranosyl}uracil

There total 1 articles about 1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-5'-(tert-butyldiphenylsilyl)-3'-deoxy-β-ribofuranosyl}uracil 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:

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 2-benzoyl-3-[(benzoyloxy)methyl]-5-(tert-butyldiphenylsilyl)-3-deoxy-1-O-methyl-α- and β-ribofuranose → 1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-5'-(tert-butyldiphenylsilyl)-3'-deoxy-β-ribofuranosyl}uracil (183374-92-7)

Guidance literature:

With TMSTf; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; Yield given. Multistep reaction; 1.) CH₃CN, 10 min, 2.) CH₃CN, 40 deg C, 12 h;

DOI:10.1021/jo960669h

Reference yield: 70.0%

1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-5'-(tert-butyldiphenylsilyl)-3'-deoxy-β-ribofuranosyl}uracil (183374-92-7) → 1-[(2R,3R,4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-4-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (183374-93-8)

Guidance literature:

With sodium hydroxide; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo960669h

Reference yield:

1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-5'-(tert-butyldiphenylsilyl)-3'-deoxy-β-ribofuranosyl}uracil (183374-92-7) → C44H48N4O14S (183375-01-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / aq. NaOH / methanol / 1 h / Ambient temperature

2: 65 percent / PPh₃, DIAD / acetonitrile; tetrahydrofuran / 2 h / Ambient temperature

3: 1.) Cs₂CO₃, 2.) Oxone, NaOAc / 1.) THF, room temperature, 3 h; DMF, 2.5 h, 2.) MeOH, THF, room temperature, 2 h

4: pyridine

5: 79 percent / Hf/pyridine / 3 h / Ambient temperature

6: 97 percent / TEA, DMAP / pyridine / 2.5 h / Ambient temperature

With pyridine; dmap; Oxone; sodium hydroxide; di-isopropyl azodicarboxylate; TEA; hydrogen fluoride; sodium acetate; caesium carbonate; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; acetonitrile;

DOI:10.1021/jo960669h

upstream raw materials:

uracil

Downstream raw materials:

1-[(2R,3R,4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-4-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Thioacetic acid S-[(2S,3S,4R,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-ylmethyl] ester

C₄₃H₄₆N₄O₁₂S

C₄₄H₄₈N₄O₁₄S