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

Base Information

• Chemical Name: 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-5'-O-(4,4'-dimethoxytrityl)-N³-pivaloyloxymethyl-2'-deoxyuridine
• CAS No.: 244631-67-2
• Molecular Formula: C₇₁H₆₈N₂O₁₉
• Molecular Weight: 1253.32

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

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

There total 9 articles about 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-5'-O-(4,4'-dimethoxytrityl)-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: 73.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N3-pivaloyloxymethyluridine (244631-66-1) → 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-5'-O-(4,4'-dimethoxytrityl)-N3-pivaloyloxymethyl-2'-deoxyuridine (244631-67-2)

Guidance literature:

In pyridine; for 3h;

Reference yield:

3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-5'-O-(4,4'-dimethoxytrityl)-N3-pivaloyloxymethyl-2'-deoxyuridine (244631-67-2)

Guidance literature:

Multi-step reaction with 7 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

7: 73 percent / pyridine / 3 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 / 7: Substitution;

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-5'-O-(4,4'-dimethoxytrityl)-N3-pivaloyloxymethyl-2'-deoxyuridine (244631-67-2)

Guidance literature:

Multi-step reaction with 6 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

6: 73 percent / pyridine / 3 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 / 6: Substitution;

upstream raw materials:

4,4'-dimethoxytrityl chloride

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

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

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

Downstream raw materials:

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

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