1-[3-O-benzoyl-2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-(benzoyl)uracil

Base Information

• Chemical Name: 1-[3-O-benzoyl-2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-(benzoyl)uracil
• CAS No.: 251296-71-6
• Molecular Formula: C₂₉H₃₄N₂O₈Si
• Molecular Weight: 566.683

Synonyms:1-[3-O-benzoyl-2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-(benzoyl)uracil

Chemical Property of 1-[3-O-benzoyl-2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-(benzoyl)uracil

Chemical Property:

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Technology Process of 1-[3-O-benzoyl-2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-(benzoyl)uracil

There total 3 articles about 1-[3-O-benzoyl-2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-(benzoyl)uracil 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: 81.0%

1-[3-O-benzoyl-2,5-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-(benzoyl)uracil (251296-70-5) → 1-[3-O-benzoyl-2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-(benzoyl)uracil (251296-71-6)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1021/jo9908647

Reference yield:

benzoyl chloride (98-88-4) → 1-[3-O-benzoyl-2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-(benzoyl)uracil (251296-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / pyridine / 20 °C

2: 81 percent / TFA; H₂O / CH₂Cl₂ / 0.75 h / 20 °C

With pyridine; water; trifluoroacetic acid; In dichloromethane; 1: Acylation / 2: desilylation;

DOI:10.1021/jo9908647

Reference yield:

2',5'-bis-O-(tert-butyldimethylsilyl)uridine (54925-66-5) → 1-[3-O-benzoyl-2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-(benzoyl)uracil (251296-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / pyridine / 20 °C

2: 81 percent / TFA; H₂O / CH₂Cl₂ / 0.75 h / 20 °C

With pyridine; water; trifluoroacetic acid; In dichloromethane; 1: Acylation / 2: desilylation;

DOI:10.1021/jo9908647

upstream raw materials:

1-[3-O-benzoyl-2,5-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-(benzoyl)uracil

benzoyl chloride

2',5'-bis-O-(tert-butyldimethylsilyl)uridine

Downstream raw materials:

5'-azido-3'-O-benzoyl-2'-O-(tert-butyldimethylsilyl)-5'-deoxyuridine

5'-amino-3'-O-benzoyl-2'-O-(tert-butyldimethylsilyl)-5'-deoxyuridine

1-[3-O-benzoyl-2-O-(tert-butyldimethylsilyl)-5-chloro-5-deoxy-β-D-ribofuranosyl]-3-N-(benzoyl)uracil

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