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

Base Information

• Chemical Name: 1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-β-D-erythro-pentofuranosyl>-N³-benzoylthymine
• CAS No.: 241817-16-3
• Molecular Formula: C₄₁H₄₂N₂O₈Si
• Molecular Weight: 718.879

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

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

There total 9 articles about 1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-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: 63.0%

benzoyl chloride (98-88-4) + 1-<3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-β-D-erythro-pentofuranosyl>-N3-benzoylthymine (241817-14-1) → 1-<5-O-benzoyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-β-D-erythro-pentofuranosyl>-N3-benzoylthymine (241817-16-3)

Guidance literature:

With pyridine; at -5 ℃; for 0.666667h;

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-β-D-erythro-pentofuranosyl>-N3-benzoylthymine (241817-16-3)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; potassium carbonate; In methanol;

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-β-D-erythro-pentofuranosyl>-N3-benzoylthymine (241817-16-3)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In methanol; dichloromethane;

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

upstream raw materials:

benzoyl chloride

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

thymin

tert-butylchlorodiphenylsilane

Downstream raw materials:

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

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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