1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-erythro-pentofuranosyl>-N³-benzoylthymine

Base Information

• Chemical Name: 1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-erythro-pentofuranosyl>-N³-benzoylthymine
• CAS No.: 241817-17-4
• Molecular Formula: C₄₅H₅₀N₂O₁₀Si
• Molecular Weight: 806.985

Synonyms:1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-erythro-pentofuranosyl>-N³-benzoylthymine

Chemical Property of 1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-erythro-pentofuranosyl>-N³-benzoylthymine

Chemical Property:

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Technology Process of 1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-erythro-pentofuranosyl>-N³-benzoylthymine

There total 10 articles about 1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-erythro-pentofuranosyl>-N³-benzoylthymine 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: 75.0%

2-Methoxyethoxymethyl chloride (3970-21-6) + 1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-β-D-erythro-pentofuranosyl>-N3-benzoylthymine (241817-16-3) → 1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-erythro-pentofuranosyl>-N3-benzoylthymine (241817-17-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 50 ℃; for 48h;

DOI:10.1016/S0968-0896(99)00061-9

Reference yield:

benzoyl chloride (98-88-4) → 1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-erythro-pentofuranosyl>-N3-benzoylthymine (241817-17-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / pyridine / 80 °C

2: 74 percent / K₂CO₃ / methanol / 0.5 h / -5 °C

3: 63 percent / pyridine / 0.67 h / -5 °C

4: 75 percent / i-Pr₂NEt / CH₂Cl₂ / 48 h / 50 °C

With pyridine; potassium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1016/S0968-0896(99)00061-9

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → 1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-erythro-pentofuranosyl>-N3-benzoylthymine (241817-17-4)

Guidance literature:

Multi-step reaction with 6 steps

1: (NH₄)2SO₄ / Heating

2: 62 percent / TMSOTf / CH₂Cl₂ / 1.) room temperature, overnight, 2.) 50 deg C, 24 h

3: 70 percent / pyridine / 80 °C

4: 74 percent / K₂CO₃ / methanol / 0.5 h / -5 °C

5: 63 percent / pyridine / 0.67 h / -5 °C

6: 75 percent / i-Pr₂NEt / CH₂Cl₂ / 48 h / 50 °C

With pyridine; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1016/S0968-0896(99)00061-9

upstream raw materials:

2-Methoxyethoxymethyl chloride

1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-β-D-erythro-pentofuranosyl>-N³-benzoylthymine

benzoyl chloride

thymin

Downstream raw materials:

1-<3-deoxy-3-C-hydroxymethyl-2-O-(2-methoxyethoxymethyl)-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl>thymine

1-<3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-erythro-pentofuranosyl>thymine

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