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

Base Information

• Chemical Name: 1-[2-O-acetyl-5-azido-3-O-benzyl-5-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5,6-dideoxy-β-D-ribofuranosyl]thymine
• CAS No.: 1400908-45-3
• Molecular Formula: C₃₇H₄₃N₅O₇Si
• Molecular Weight: 697.863

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

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

Chemical Property:

Purity/Quality:

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

There total 8 articles about 1-[2-O-acetyl-5-azido-3-O-benzyl-5-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5,6-dideoxy-β-D-ribofuranosyl]thymine 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%

C34H41N3O7Si + thymin (65-71-4,28806-14-6,691841-57-3) → 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)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 75 ℃; for 5h; Inert atmosphere;

DOI:10.1055/s-0031-1289783

Reference yield:

C19H26O7 (843674-28-2) → 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)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1055/s-0031-1289783

Reference yield:

5-O-acetyl-3-O-benzyl-7-O-(tert-butyldiphenylsilyl)-6-deoxy-1,2-O-isopropylidene-α-D-allo-hepto-1,4-furanose (1400908-42-0) → 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)

Guidance literature:

Multi-step reaction with 5 steps

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

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

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

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

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

With sodium azide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; potassium carbonate; acetic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 5: Vorbruggen glycosylation;

DOI:10.1055/s-0031-1289783

upstream raw materials:

C₁₉H₂₆O₇

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

thymin

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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