5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N³-pivaloyloxymethyluridine

Base Information

• Chemical Name: 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N³-pivaloyloxymethyluridine
• CAS No.: 244631-66-1
• Molecular Formula: C₅₀H₅₀N₂O₁₇
• Molecular Weight: 950.95

Synonyms:5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N³-pivaloyloxymethyluridine

Chemical Property of 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N³-pivaloyloxymethyluridine

Chemical Property:

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Technology Process of 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N³-pivaloyloxymethyluridine

There total 8 articles about 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N³-pivaloyloxymethyluridine 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: 91.0%

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) → 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N3-pivaloyloxymethyluridine (244631-66-1)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In pyridine; for 16h;

Reference yield:

3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N3-pivaloyloxymethyluridine (244631-66-1)

Guidance literature:

Multi-step reaction with 6 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

6: 91 percent / Et₃N*3HF / pyridine / 16 h

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

Reference yield:

3',5'-di-O-tert-butyldimethylsilyl N3-pivaloyloxymethyl-2'-deoxythymidine (196200-56-3) → 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N3-pivaloyloxymethyluridine (244631-66-1)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 0.71 g / dimethylformamide / 0.5 h

3: 69 percent / K₂CO₃ / methanol / 1 h

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

5: 91 percent / Et₃N*3HF / pyridine / 16 h

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

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

5-(aminomethyl)-2'-deoxyuridine

5-(β-D-glucopyranosyloxymethyl)-2'-deoxyuridine

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