1-[(2R,4S,5S)-5-Bromomethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2R,4S,5S)-5-Bromomethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 183375-05-5
• Molecular Formula: C₂₆H₃₁BrN₂O₄Si
• Molecular Weight: 543.533

Synonyms:1-[(2R,4S,5S)-5-Bromomethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property of 1-[(2R,4S,5S)-5-Bromomethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

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Technology Process of 1-[(2R,4S,5S)-5-Bromomethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

There total 2 articles about 1-[(2R,4S,5S)-5-Bromomethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 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: 94.0%

5’-bromo-5’-deoxythymidine (25905-51-5) + tert-butylchlorodiphenylsilane (58479-61-1) → 1-[(2R,4S,5S)-5-Bromomethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (183375-05-5)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; at 40 ℃; for 14h;

DOI:10.1021/jo960669h

Reference yield:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 1-[(2R,4S,5S)-5-Bromomethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (183375-05-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / PPH₃, CBr₄ / pyridine / 1 h

2: 94 percent / imidazole / tetrahydrofuran / 14 h / 40 °C

With 1H-imidazole; carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; pyridine;

DOI:10.1021/jo960669h

Reference yield: 52.0%

1-[(2R,4S,5S)-5-Bromomethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (183375-05-5) + Thioacetic acid S-[(2S,3S,4R,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-ylmethyl] ester (183374-94-9) → C52H62N4O9SSi2 + C54H64N4O10SSi2 (183375-07-7)

Guidance literature:

With caesium carbonate; In tetrahydrofuran; for 10h; Ambient temperature;

DOI:10.1021/jo960669h

upstream raw materials:

5’-bromo-5’-deoxythymidine

tert-butylchlorodiphenylsilane

thymidine

Downstream raw materials:

C₅₄H₆₄N₄O₁₀SSi₂

C₄₃H₄₆N₄O₁₂S

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