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

Base Information

• Chemical Name: 1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 83467-48-5
• Molecular Formula: C₂₆H₃₂N₂O₅Si
• Molecular Weight: 480.636

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

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

Chemical Property:

Purity/Quality:

99.3% ^*data from raw suppliers

3’-O-tert-Butyldiphenylsilylthymidine ^*data from reagent suppliers

Safty Information:

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

There total 35 articles about 1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-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: 100.0%

5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) + tert-butylchlorodiphenylsilane (58479-61-1) → 1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (83467-48-5)

Guidance literature:

5'-O-(4-4'-dimethoxytrityl)thymidine; tert-butylchlorodiphenylsilane; With 1H-imidazole; In dichloromethane; at 20 ℃; for 2h;

With toluene-4-sulfonic acid; In methanol;

Reference yield: 100.0%

1-[(2R,4S,5R)-5-[bis(4-methoxyphenyl)phenylmethoxymethyl]-4-(tert-butyldiphenylsilanyloxy)tetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (198267-31-1) → 1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (83467-48-5)

Guidance literature:

With Amberlyst 15-H; In methanol; at 20 ℃; for 30h;

DOI:10.1021/jo001223a

Reference yield: 99.0%

1-[(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(1,1-dimethylethyl)diphenylsilyl]oxy}tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (289681-49-8) → 1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (83467-48-5)

Guidance literature:

With trifluoroacetic acid; In methanol; for 2.5h; Inert atmosphere;

upstream raw materials:

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

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

5'-O-(tert-butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)thymidine

5'-O-(4-4'-dimethoxytrityl)thymidine

Downstream raw materials:

(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid

1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil

3'-O-tert-Butyldiphenylsilyl-5'-O-methanesulfonyl-thymidine

(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid tert-butyl ester

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