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

Base Information

• Chemical Name: (5S,6S)-5-bromo-O⁶-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilylthymidine
• CAS No.: 161922-92-5
• Molecular Formula: C₂₆H₃₁BrN₂O₅Si
• Molecular Weight: 559.532

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

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

Chemical Property:

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

There total 6 articles about (5S,6S)-5-bromo-O⁶-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilylthymidine 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: 49.0%

1'-O-methyl-2'-deoxy-3'-O-tert-butyldiphenylsilyl-5'-O6-(5-bromo-5-methyl-6-hydro-1H-pyrimidine-2,4-dione) riboside → (5S,6S)-5-bromo-O6-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilylthymidine (161922-92-5)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 1.5h;

DOI:10.1055/s-1994-25717

Reference yield: 35.0%

1'-O-methyl-2'-deoxy-3'-O-tert-butyldiphenylsilyl-5'-O6-(5-bromo-5-methyl-6-hydro-1H-pyrimidine-2,4-dione) riboside → (5S,6S)-5-bromo-O6-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilylthymidine (161922-92-5) + (5R,6R)-5-Bromo-6-[(2R,3S)-3-(tert-butyl-diphenyl-silanyloxy)-5-methoxy-tetrahydro-furan-2-ylmethoxy]-5-methyl-dihydro-pyrimidine-2,4-dione

Guidance literature:

With zirconocene dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1055/s-1994-25717

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → (5S,6S)-5-bromo-O6-5'-cyclo-6-hydro-2'-deoxy-3'-O-tert-butyldiphenylsilylthymidine (161922-92-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NBS, TFA / dimethylformamide / 7 h / Ambient temperature

2: imidazole / dimethylformamide / 12 h / Ambient temperature

3: 49 percent / 4A molecular sieves, BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / 0 - 20 °C

With 1H-imidazole; N-Bromosuccinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-1994-25717

upstream raw materials:

thymin

tert-butylchlorodiphenylsilane

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

Downstream raw materials:

1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

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