1-{4-(tert-butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-{4-(tert-butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-1H-pyrimidine-2,4-dione
CAS No.:223638-13-9
Molecular Formula:C₄₀H₆₄N₂O₇Si₃
Molecular Weight:769.214
Hs Code.:

1-{4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-5-[3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-1<i>H</i>-pyrimidine-2,4-dione

Synonyms:1-{4-(tert-butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-1H-pyrimidine-2,4-dione

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Chemical Property of 1-{4-(tert-butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-1H-pyrimidine-2,4-dione

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Technology Process of 1-{4-(tert-butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-1H-pyrimidine-2,4-dione

There total 7 articles about 1-{4-(tert-butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-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: 89.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 223637-97-6
1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(3-hydroxy-prop-1-ynyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-1H-pyrimidine-2,4-dione

: 223638-13-9
1-{4-(tert-butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-1H-pyrimidine-2,4-dione

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 18h; Ambient temperature;
DOI:10.1016/S0040-4039(99)00483-9

Reference yield:

: 88023-78-3
para-methoxybenzyl chloride

: 223638-13-9
1-{4-(tert-butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / DBU / acetonitrile / 2.5 h / 0 °C

2: 61 percent / TFA / tetrahydrofuran; H₂O / 9.5 h / Ambient temperature

3: oxalyl chloride, DMSO / CH₂Cl₂ / 1.5 h / -78 °C

4: NEt₃ / 24 h / 0 - 20 °C

5: 52 percent / LDA / tetrahydrofuran / -78 deg C, 30 min then 0 deg C to r.t., 2 h

6: 86 percent / CuI, Pd(PPh₃)2Cl₂, NEt₃ / 24 h / Ambient temperature

7: 89 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

With 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; oxalyl dichloride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(99)00483-9

Reference yield:

: 3-(tert-butyl-dimethyl-silanyloxy)-5-[3-(4-methoxy-benzyloxymethyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-carbaldehyde

: 223638-13-9
1-{4-(tert-butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 4 steps

1: NEt₃ / 24 h / 0 - 20 °C

2: 52 percent / LDA / tetrahydrofuran / -78 deg C, 30 min then 0 deg C to r.t., 2 h

3: 86 percent / CuI, Pd(PPh₃)2Cl₂, NEt₃ / 24 h / Ambient temperature

4: 89 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

With 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(99)00483-9