1-(5-O-benzyl-2,3-dideoxy-3-fluoro-2-phenylselenenyl-α,β-D-ribofuranosyl)-N³-benzoylthymine

Base Information

• Chemical Name: 1-(5-O-benzyl-2,3-dideoxy-3-fluoro-2-phenylselenenyl-α,β-D-ribofuranosyl)-N³-benzoylthymine
• CAS No.: 220718-14-9
• Molecular Formula: C₃₀H₂₇FN₂O₅Se
• Molecular Weight: 593.513

Synonyms:1-(5-O-benzyl-2,3-dideoxy-3-fluoro-2-phenylselenenyl-α,β-D-ribofuranosyl)-N³-benzoylthymine

Chemical Property of 1-(5-O-benzyl-2,3-dideoxy-3-fluoro-2-phenylselenenyl-α,β-D-ribofuranosyl)-N³-benzoylthymine

Chemical Property:

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Technology Process of 1-(5-O-benzyl-2,3-dideoxy-3-fluoro-2-phenylselenenyl-α,β-D-ribofuranosyl)-N³-benzoylthymine

There total 2 articles about 1-(5-O-benzyl-2,3-dideoxy-3-fluoro-2-phenylselenenyl-α,β-D-ribofuranosyl)-N³-benzoylthymine 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: 58.0%

N-3-benzoylthymine (4330-20-5) + phenyl 5-O-benzyl-3-deoxy-3-fluoro-1-seleno-α-D-arabino-furanoside (220718-13-8) → 1-(5-O-benzyl-2,3-dideoxy-3-fluoro-2-phenylselenenyl-α,β-D-ribofuranosyl)-N3-benzoylthymine (220718-14-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In N,N-dimethyl-formamide;

DOI:10.1021/jo980911f

Reference yield:

Benzeneselenol (645-96-5) → 1-(5-O-benzyl-2,3-dideoxy-3-fluoro-2-phenylselenenyl-α,β-D-ribofuranosyl)-N3-benzoylthymine (220718-14-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / boron trifluoride ethyl etherate / CH₂Cl₂ / 3 h / 20 °C

2: 84 percent / ammonia / methanol / 4 h / 0 °C

3: 58 percent / Ph₃P; DEAD / dimethylformamide

With boron trifluoride diethyl etherate; ammonia; triphenylphosphine; diethylazodicarboxylate; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Deacetylation / 3: Condensation;

DOI:10.1021/jo980911f

Reference yield:

1-(5-O-benzyl-2,3-dideoxy-3-fluoro-2-phenylselenenyl-α,β-D-ribofuranosyl)-N3-benzoylthymine (220718-14-9) → 3-Benzoyl-1-((4S,5R)-5-benzyloxymethyl-4-fluoro-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 1h; Heating;

DOI:10.1021/jo980911f

upstream raw materials:

N-3-benzoylthymine

phenyl 5-O-benzyl-3-deoxy-3-fluoro-1-seleno-α-D-arabino-furanoside

Benzeneselenol

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