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

Base Information

Chemical Name:5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-deoxy-5-C-[(S)-2-hydroxyethyl]thymidine
CAS No.:1400908-48-6
Molecular Formula:C₂₇H₃₁N₅O₇
Molecular Weight:537.572
Hs Code.:

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

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

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

There total 11 articles about 5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-deoxy-5-C-[(S)-2-hydroxyethyl]thymidine 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: 75.0%

: 1400908-47-5
5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5'-deoxythymidine

: 1400908-48-6
5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-deoxy-5-C-[(S)-2-hydroxyethyl]thymidine

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1.5h; Inert atmosphere;
DOI:10.1055/s-0031-1289783

Reference yield:

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

: 1400908-48-6
5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-deoxy-5-C-[(S)-2-hydroxyethyl]thymidine

Guidance literature:: Multi-step reaction with 2 steps

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

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; potassium carbonate; In tetrahydrofuran; methanol;
DOI:10.1055/s-0031-1289783

Reference yield:

: 843674-28-2
C₁₉H₂₆O₇

: 1400908-48-6
5'-azido-3'-O-benzyl-3-N-(benzyloxymethyl)-5'-deoxy-5-C-[(S)-2-hydroxyethyl]thymidine

Guidance literature:: Multi-step reaction with 11 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

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

11: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; sodium azide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetrabutyl ammonium fluoride; 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