N⁴-benzoyl-1-<(5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-α-D-erythro-pentofuranosyl>uracil

Base Information

• Chemical Name: N⁴-benzoyl-1-<(5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-α-D-erythro-pentofuranosyl>uracil
• CAS No.: 175544-75-9
• Molecular Formula: C₃₃H₃₇N₃O₄Si
• Molecular Weight: 567.76

Synonyms:N⁴-benzoyl-1-<(5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-α-D-erythro-pentofuranosyl>uracil

Chemical Property of N⁴-benzoyl-1-<(5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-α-D-erythro-pentofuranosyl>uracil

Chemical Property:

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Technology Process of N⁴-benzoyl-1-<(5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-α-D-erythro-pentofuranosyl>uracil

There total 6 articles about N⁴-benzoyl-1-<(5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-α-D-erythro-pentofuranosyl>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: 40.9%

N4,O-bis(trimethylsilyl)-N4-benzoylcytosine (64339-87-3) + Acetic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-methyl-tetrahydro-furan-2-yl ester → N4-benzoyl-1-<(5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-α-D-erythro-pentofuranosyl>uracil (175544-75-9) + N4-benzoyl-1-<(5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-β-D-erythro-pentofuranosyl>uracil (175544-72-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 0.583333h; Ambient temperature;

DOI:10.1080/07328319608002379

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → N4-benzoyl-1-<(5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-α-D-erythro-pentofuranosyl>uracil (175544-75-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

2: 58.7 percent / LDA / tetrahydrofuran / 2 h / -78 °C

3: 74.6 percent / DIBALH / CH₂Cl₂ / 2 h / -78 °C

4: 86.6 percent / Py, DMAP / CH₂Cl₂ / 2 h / 0 °C

5: 29.4 percent / trimethylsilyl trifluoromethane sulfonate / 1,2-dichloro-ethane / 0.58 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1080/07328319608002379

Reference yield:

4-N-benzoylcytosine (26661-13-2) → N4-benzoyl-1-<(5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-α-D-erythro-pentofuranosyl>uracil (175544-75-9)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium sulfate / 3 h / Heating

2: 29.4 percent / trimethylsilyl trifluoromethane sulfonate / 1,2-dichloro-ethane / 0.58 h / Ambient temperature

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane;

DOI:10.1080/07328319608002379

upstream raw materials:

N₄,O-bis(trimethylsilyl)-N₄-benzoylcytosine

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

4-N-benzoylcytosine

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

Downstream raw materials:

1-(2,3-dideoxy-2-C-methyl-α-D-erythro-pentofuranosyl)cytosine

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