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
Hs Code.:

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

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

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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:

: 66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6
uracil

: 2-benzoyl-3-[(benzoyloxy)methyl]-5-(tert-butyldiphenylsilyl)-3-deoxy-1-O-methyl-α- and β-ribofuranose

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

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%

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

: 183374-93-8
1-[(2R,3R,4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-4-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Guidance literature:: With sodium hydroxide; In methanol; for 1h; Ambient temperature;
DOI:10.1021/jo960669h

Reference yield:

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

: 183375-01-1
C₄₄H₄₈N₄O₁₄S

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