2'-O-acetyl-5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5'-deoxythymidine

Base Information

• Chemical Name: 2'-O-acetyl-5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5'-deoxythymidine
• CAS No.: 1400908-46-4
• Molecular Formula: C₄₅H₅₁N₅O₈Si
• Molecular Weight: 818.014

Synonyms:2'-O-acetyl-5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5'-deoxythymidine

Chemical Property of 2'-O-acetyl-5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5'-deoxythymidine

Chemical Property:

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Technology Process of 2'-O-acetyl-5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5'-deoxythymidine

There total 9 articles about 2'-O-acetyl-5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5'-deoxythymidine 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: 76.0%

Benzyloxymethyl chloride (3587-60-8) + 1-[2-O-acetyl-5-azido-3-O-benzyl-5-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5,6-dideoxy-β-D-ribofuranosyl]thymine (1400908-45-3) → 2'-O-acetyl-5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5'-deoxythymidine (1400908-46-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile; at 10 - 20 ℃; for 4.25h; Inert atmosphere;

DOI:10.1055/s-0031-1289783

Reference yield:

C19H26O7 (843674-28-2) → 2'-O-acetyl-5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5'-deoxythymidine (1400908-46-4)

Guidance literature:

Multi-step reaction with 9 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 3.17 h / 0 - 25 °C / Inert atmosphere

2: 1H-imidazole / dichloromethane / 1 h / 25 °C / Inert atmosphere

3: pyridine / 3 h / 25 °C / Inert atmosphere

4: potassium carbonate / methanol / 0.5 h / 25 °C / Inert atmosphere

5: triethylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere

6: sodium azide / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere

7: sulfuric acid; acetic acid / 2 h / 0 °C / Inert atmosphere

8: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 5 h / 0 - 75 °C / Inert atmosphere

9: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; acetonitrile / 4.25 h / 10 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; sodium azide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 8: Vorbruggen glycosylation;

DOI:10.1055/s-0031-1289783

Reference yield:

C33H42O6Si → 2'-O-acetyl-5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5'-deoxythymidine (1400908-46-4)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 3 h / 25 °C / Inert atmosphere

2: potassium carbonate / methanol / 0.5 h / 25 °C / Inert atmosphere

3: triethylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere

4: sodium azide / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere

5: sulfuric acid; acetic acid / 2 h / 0 °C / Inert atmosphere

6: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 5 h / 0 - 75 °C / Inert atmosphere

7: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; acetonitrile / 4.25 h / 10 - 20 °C / Inert atmosphere

With pyridine; sodium azide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 6: Vorbruggen glycosylation;

DOI:10.1055/s-0031-1289783

upstream raw materials:

Benzyloxymethyl chloride

1-[2-O-acetyl-5-azido-3-O-benzyl-5-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5,6-dideoxy-β-D-ribofuranosyl]thymine

C₁₉H₂₆O₇

5-O-acetyl-3-O-benzyl-7-O-(tert-butyldiphenylsilyl)-6-deoxy-1,2-O-isopropylidene-α-D-allo-hepto-1,4-furanose

Downstream raw materials:

5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5'-deoxythymidine

5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-deoxy-5-C-[(S)-2-hydroxyethyl]thymidine

5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-deoxy-2'-O-methyl-5'-C-[(S)-2-methoxyethyl]thymidine

5'-amino-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-deoxy-2'-O-methyl-5'-C-[(S)-2-methoxyethyl]thymidine

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