5-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine

Base Information

• Chemical Name: 5-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine
• CAS No.: 244631-68-3
• Molecular Formula: C₄₇H₇₄N₂O₁₆Si₂
• Molecular Weight: 979.279

Synonyms:5-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine

Chemical Property of 5-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine

Chemical Property:

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Technology Process of 5-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine

There total 8 articles about 5-(2-O-benzyl-3,4,6-tri-O-acetyl-α-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: 66.0%

O-(3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranosyl)trichloroacetimidate + 3',5'-di-O-tert-butyldimethylsilyl-5-hydroxymethyl-N3-pivaloyloxymethyl-2'-deoxyuridine (244631-62-7) → 5-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N3-pivaloyloxymethyl-2'-deoxyuridine (244631-68-3)

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-O-benzyl-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N3-pivaloyloxymethyl-2'-deoxyuridine (244631-68-3)

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: 66 percent / powdered molecular sieves 4 Angstroem; TMSOTf / 1,2-dichloro-ethane / 1.5 h

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; bromine; potassium carbonate; In methanol; tetrachloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: silylation / 2: Substitution / 3: Bromination / 4: Acetoxylation / 5: Deacetylation / 6: glucosylation;

Reference yield:

3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → 5-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N3-pivaloyloxymethyl-2'-deoxyuridine (244631-68-3)

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: 66 percent / powdered molecular sieves 4 Angstroem; TMSOTf / 1,2-dichloro-ethane / 1.5 h

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; bromine; potassium carbonate; In methanol; tetrachloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: Substitution / 2: Bromination / 3: Acetoxylation / 4: Deacetylation / 5: glucosylation;

upstream raw materials:

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

tert-butyldimethylsilyl chloride

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

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

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