5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine

Base Information

• Chemical Name: 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine
• CAS No.: 244631-64-9
• Molecular Formula: C₆₂H₇₈N₂O₁₇Si₂
• Molecular Weight: 1179.48

Synonyms:5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine

Chemical Property of 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine

Chemical Property:

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Technology Process of 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine

There total 8 articles about 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine 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: 96.0%

3',5'-di-O-tert-butyldimethylsilyl-5-hydroxymethyl-N3-pivaloyloxymethyl-2'-deoxyuridine (244631-62-7) + 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (149707-75-5) → 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N3-pivaloyloxymethyl-2'-deoxyuridine (244631-64-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In 1,2-dichloro-ethane; for 1.5h;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N3-pivaloyloxymethyl-2'-deoxyuridine (244631-64-9)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 1 h / 20 °C

2: 98 percent / K₂CO₃ / dimethylformamide

3: Br₂ / CCl₄ / 2 h / Heating; Irradiation

4: 0.71 g / dimethylformamide / 0.5 h

5: 69 percent / K₂CO₃ / methanol / 1 h

6: 60 percent / HgBr₂; Hg(CN)2; powdered molecular sieves, 4 Angstroem / acetonitrile / 3 h

With 1H-imidazole; molecular sieve; 4 A molecular sieve; bromine; mercury(II) cyanide; potassium carbonate; mercury dibromide; In methanol; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile; 1: silylation / 2: Substitution / 3: Bromination / 4: Acetoxylation / 5: Deacetylation / 6: Condensation;

Reference yield:

3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N3-pivaloyloxymethyl-2'-deoxyuridine (244631-64-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / K₂CO₃ / dimethylformamide

2: Br₂ / CCl₄ / 2 h / Heating; Irradiation

3: 0.71 g / dimethylformamide / 0.5 h

4: 69 percent / K₂CO₃ / methanol / 1 h

5: 60 percent / HgBr₂; Hg(CN)2; powdered molecular sieves, 4 Angstroem / acetonitrile / 3 h

With molecular sieve; 4 A molecular sieve; bromine; mercury(II) cyanide; potassium carbonate; mercury dibromide; In methanol; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Bromination / 3: Acetoxylation / 4: Deacetylation / 5: Condensation;

upstream raw materials:

3',5'-di-O-tert-butyldimethylsilyl-5-hydroxymethyl-N³-pivaloyloxymethyl-2'-deoxyuridine

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

tert-butyldimethylsilyl chloride

3',5'-O-di(tert-butyldimethylsilyl)thymidine

Downstream raw materials:

5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-5'-O-(4,4'-dimethoxytrityl)-N³-pivaloyloxymethyl-2'-deoxyuridine

N⁴-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine

N⁴-benzoyl-3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine

N⁴-benzoyl-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine

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