(6S)-5,5-dibromo-O⁶-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilyluridine

Base Information

• Chemical Name: (6S)-5,5-dibromo-O⁶-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilyluridine
• CAS No.: 161922-93-6
• Molecular Formula: C₂₅H₂₈Br₂N₂O₅Si
• Molecular Weight: 624.401

Synonyms:(6S)-5,5-dibromo-O⁶-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilyluridine

Chemical Property of (6S)-5,5-dibromo-O⁶-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilyluridine

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Technology Process of (6S)-5,5-dibromo-O⁶-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilyluridine

There total 4 articles about (6S)-5,5-dibromo-O⁶-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilyluridine 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: 38.0%

1'-O-methyl-2'-deoxy-3'-O-tert-butyldiphenylsilyl-5'-O6-(5,5-dibromo-6-hydro-1H-pyrimidine-2,4-dione) riboside → (6S)-5,5-dibromo-O6-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilyluridine (161922-93-6) + (R)-5,5-Dibromo-6-[(2R,3S)-3-(tert-butyl-diphenyl-silanyloxy)-5-methoxy-tetrahydro-furan-2-ylmethoxy]-dihydro-pyrimidine-2,4-dione

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 0 - 20 ℃; for 5h;

DOI:10.1055/s-1994-25717

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (6S)-5,5-dibromo-O6-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilyluridine (161922-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 12 h / Ambient temperature

2: 48 percent / 4A molecular sieves, TMSOTf / CH₂Cl₂ / 5 h / 0 - 20 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-1994-25717

Reference yield:

5,5-Dibromo-6-((2R,3S)-3-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethoxy)-dihydro-pyrimidine-2,4-dione → (6S)-5,5-dibromo-O6-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilyluridine (161922-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 12 h / Ambient temperature

2: 48 percent / 4A molecular sieves, TMSOTf / CH₂Cl₂ / 5 h / 0 - 20 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-1994-25717

upstream raw materials:

tert-butylchlorodiphenylsilane

1-O-methyl-2-deoxy-D-ribofuranoside

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