1-[2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]thymine

Base Information

• Chemical Name: 1-[2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]thymine
• CAS No.: 774226-09-4
• Molecular Formula: C₃₄H₃₈N₂O₆SeSi
• Molecular Weight: 677.731

Synonyms:1-[2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]thymine

Chemical Property of 1-[2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]thymine

Chemical Property:

Purity/Quality:

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Technology Process of 1-[2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]thymine

There total 8 articles about 1-[2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]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: 88.0%

1-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]thymine (180699-58-5) + acetic anhydride (108-24-7) → 1-[2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]thymine (774226-09-4)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1081/NCN-120030721

Reference yield:

1-(3-deoxy-3-phenylseleno-β-D-arabinofuranosyl)thymine (774226-13-0) → 1-[2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]thymine (774226-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / pyridine / 20 °C

2: 88 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1081/NCN-120030721

Reference yield:

1-(3-deoxy-3-phenylseleno-5-O-trityl-β-D-arabinofuranosyl)thymine (774226-07-2) → 1-[2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]thymine (774226-09-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / aq. AcOH / 1 h / 80 °C

2: 75 percent / pyridine / 20 °C

3: 88 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; acetic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1081/NCN-120030721

upstream raw materials:

1-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]thymine

acetic anhydride

1-(3-deoxy-3-phenylseleno-β-D-arabinofuranosyl)thymine

1-(3-deoxy-3-phenylseleno-5-O-trityl-β-D-arabinofuranosyl)thymine

Downstream raw materials:

5'-O-(tert-butyldiphenylsilyl)-4'-cyano-2',3'-didehydro-3'-deoxythymidine

1-[2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-β-D-glycero-pent-3-enofuranosyl]thymine

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