9-[5-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-phenylselenenyl-β-D-xylofuranosyl]adenine

Base Information

• Chemical Name: 9-[5-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-phenylselenenyl-β-D-xylofuranosyl]adenine
• CAS No.: 134100-24-6
• Molecular Formula: C₂₂H₃₁N₅O₃SeSi
• Molecular Weight: 520.565

Synonyms:9-[5-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-phenylselenenyl-β-D-xylofuranosyl]adenine

Chemical Property of 9-[5-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-phenylselenenyl-β-D-xylofuranosyl]adenine

Chemical Property:

Purity/Quality:

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Technology Process of 9-[5-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-phenylselenenyl-β-D-xylofuranosyl]adenine

There total 3 articles about 9-[5-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-phenylselenenyl-β-D-xylofuranosyl]adenine 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: 87.0%

diphenyl diselenide (1666-13-3) + 9-<2,3-anhydro-5-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>adenine (128803-97-4) → 9-[5-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-phenylselenenyl-β-D-xylofuranosyl]adenine (134100-24-6)

Guidance literature:

diphenyl diselenide; With lithium aluminium tetrahydride; In 1,4-dioxane; for 0.5h;

9-<2,3-anhydro-5-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>adenine; In 1,4-dioxane; for 4h; Heating;

DOI:10.1016/S0040-4020(02)00153-9

Reference yield:

9-(2,3-anhydro-β-D-ribofuranosyl)adenine (2627-64-7) → 9-[5-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-phenylselenenyl-β-D-xylofuranosyl]adenine (134100-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / imidazole / dimethylformamide / 0.42 h / 0 °C

2.1: LiAlH₄ / dioxane / 0.5 h

2.2: 87 percent / dioxane / 4 h / Heating

With 1H-imidazole; lithium aluminium tetrahydride; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(02)00153-9

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 9-[5-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-phenylselenenyl-β-D-xylofuranosyl]adenine (134100-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / imidazole / dimethylformamide / 0.42 h / 0 °C

2.1: LiAlH₄ / dioxane / 0.5 h

2.2: 87 percent / dioxane / 4 h / Heating

With 1H-imidazole; lithium aluminium tetrahydride; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(02)00153-9

upstream raw materials:

diphenyl diselenide

9-<2,3-anhydro-5-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>adenine

9-(2,3-anhydro-β-D-ribofuranosyl)adenine

tert-butyldimethylsilyl chloride

Downstream raw materials:

Acetic acid (2R,3S,5S)-2-(6-amino-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1-phenyl-meth-(E)-ylidene]-tetrahydro-furan-3-yl ester

Propionic acid (2R,3S,4S,5R)-2-(6-amino-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-phenylselanyl-tetrahydro-furan-3-yl ester

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