1-[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
CAS No.:183892-43-5
Molecular Formula:C₃₉H₅₂N₂O₆Si₂
Molecular Weight:701.023
Hs Code.:

1-[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

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

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

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

There total 5 articles about 1-[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(hydroxy-phenyl-methyl)-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: 79.0%

: 100-58-3
phenylmagnesium bromide

: 162052-68-8
3'-O-tert-Butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-formyl-thymidin

: 183892-43-5
1-[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: With copper(l) iodide; In tetrahydrofuran; 1.) 2 h, -5 deg C, 2.) 1 h, 0 deg C;
DOI:10.1002/hlca.19960790720

Reference yield:

: 139925-90-9
1-[(2R,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

: 183892-43-5
1-[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 4 steps

1: 1H-imidazole / dimethylformamide / 24 h / 25 °C

2: 80percent aq. AcOH / tetrahydrofuran / 24 h / 25 °C

3: 95 percent / trichloroacetic anhydride, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / -70 °C

4: 79 percent / CuI / tetrahydrofuran / 1.) 2 h, -5 deg C, 2.) 1 h, 0 deg C

With 1H-imidazole; copper(l) iodide; acetic acid; dimethyl sulfoxide; triethylamine; trichloroacetic acid anhydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/hlca.19960790720

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 183892-43-5
1-[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 4 steps

1: 1H-imidazole / dimethylformamide / 24 h / 25 °C

2: 80percent aq. AcOH / tetrahydrofuran / 24 h / 25 °C

3: 95 percent / trichloroacetic anhydride, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / -70 °C

4: 79 percent / CuI / tetrahydrofuran / 1.) 2 h, -5 deg C, 2.) 1 h, 0 deg C

With 1H-imidazole; copper(l) iodide; acetic acid; dimethyl sulfoxide; triethylamine; trichloroacetic acid anhydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/hlca.19960790720