3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O₄-(phenoxyacetyloxybutyl)thymidine

Base Information

• Chemical Name: 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O₄-(phenoxyacetyloxybutyl)thymidine
• CAS No.: 1396763-92-0
• Molecular Formula: C₄₉H₆₀N₂O₁₀Si
• Molecular Weight: 865.108

Synonyms:3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O₄-(phenoxyacetyloxybutyl)thymidine

Chemical Property of 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O₄-(phenoxyacetyloxybutyl)thymidine

Chemical Property:

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Technology Process of 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O₄-(phenoxyacetyloxybutyl)thymidine

There total 2 articles about 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O₄-(phenoxyacetyloxybutyl)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: 75.1%

3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O4-(hydroxybutyl)thymidine (1396763-84-0) + Phenoxyacetyl chloride (701-99-5) → 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O4-(phenoxyacetyloxybutyl)thymidine (1396763-92-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 1.91667h; Cooling with ice;

DOI:10.1039/c2ob25705j

Reference yield:

3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[5-methyl-4-triazolylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside (80971-34-2) → 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O4-(phenoxyacetyloxybutyl)thymidine (1396763-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,4-dioxane / 15 h

2: triethylamine / tetrahydrofuran / 1.92 h / Cooling with ice

With triethylamine; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1039/c2ob25705j

Reference yield: 94.1%

3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O4-(phenoxyacetyloxybutyl)thymidine (1396763-92-0) → 5'-O-(4,4'-dimethoxytrityl)-O4-(phenoxyacetyloxybutyl)thymidine (1396763-94-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.25h;

DOI:10.1039/c2ob25705j

upstream raw materials:

3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O₄-(hydroxybutyl)thymidine

Phenoxyacetyl chloride

3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[5-methyl-4-triazolylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-O₄-(phenoxyacetyloxybutyl)thymidine

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