1-[7a-(tert-butyl-diphenyl-silanyloxymethyl)-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-[7a-(tert-butyl-diphenyl-silanyloxymethyl)-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
CAS No.:500773-47-7
Molecular Formula:C₂₉H₃₄N₂O₅Si
Molecular Weight:518.685
Hs Code.:

1-[7a-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-3,3a,5,7a-tetrahydro-2<i>H</i>-furo[3,2-<i>b</i>]pyran-2-yl]-5-methyl-1<i>H</i>-pyrimidine-2,4-dione

Synonyms:1-[7a-(tert-butyl-diphenyl-silanyloxymethyl)-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

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Chemical Property of 1-[7a-(tert-butyl-diphenyl-silanyloxymethyl)-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

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Technology Process of 1-[7a-(tert-butyl-diphenyl-silanyloxymethyl)-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

There total 11 articles about 1-[7a-(tert-butyl-diphenyl-silanyloxymethyl)-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-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: 74.0%

: 500773-46-6
1-[4-allyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

: 500773-47-7
1-[7a-(tert-butyl-diphenyl-silanyloxymethyl)-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 25 ℃; for 4h;
DOI:10.1016/S0040-4039(02)01926-3

Reference yield:

: 40733-28-6
5'-tert-butyldimethylsilyloxy-2'-deoxythymidine

: 500773-47-7
1-[7a-(tert-butyl-diphenyl-silanyloxymethyl)-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 10 steps

1.1: 80 percent / NaH in oil / tetrahydrofuran / 4 h / 40 °C / ultrasound irradiation

2.1: 96 percent / n-tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: DCC; pyridinium trifluoroacetate / dimethylsulfoxide / 12 h / 20 °C

4.1: aq NaOH / dioxane / 6 h / 20 °C

4.2: NaBH₄ / dioxane / 0.5 h / 20 °C

5.1: 64 percent / pyridine / 3 h / 20 °C

6.1: imidazole / dimethylformamide / 12 h / 20 °C

7.1: 67 percent / aq. AcOH / tetrahydrofuran / 24 h / 20 °C

8.1: 98 percent / Dess-Martin periodinane; H₂O / CH₂Cl₂ / 1 h / 20 °C

9.1: 89 percent / tetrahydrofuran / 2.5 h / -78 - 0 °C

10.1: 74 percent / Grubbs' second generation catalyst / CH₂Cl₂ / 4 h / 25 °C

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium hydroxide; tetrabutyl ammonium fluoride; water; pyridinium trifluroacetate; sodium hydride; Dess-Martin periodane; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 3.1: Moffatt method / 9.1: Wittig reaction;
DOI:10.1016/S0040-4039(02)01926-3

Reference yield:

: 50-89-5,28854-96-8,3545-96-8,50-88-4
thymidine

: 500773-47-7
1-[7a-(tert-butyl-diphenyl-silanyloxymethyl)-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 11 steps

1.1: 87 percent / imidazole / dimethylformamide / 6 h / 20 °C

2.1: 80 percent / NaH in oil / tetrahydrofuran / 4 h / 40 °C / ultrasound irradiation

3.1: 96 percent / n-tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4.1: DCC; pyridinium trifluoroacetate / dimethylsulfoxide / 12 h / 20 °C

5.1: aq NaOH / dioxane / 6 h / 20 °C

5.2: NaBH₄ / dioxane / 0.5 h / 20 °C

6.1: 64 percent / pyridine / 3 h / 20 °C

7.1: imidazole / dimethylformamide / 12 h / 20 °C

8.1: 67 percent / aq. AcOH / tetrahydrofuran / 24 h / 20 °C

9.1: 98 percent / Dess-Martin periodinane; H₂O / CH₂Cl₂ / 1 h / 20 °C

10.1: 89 percent / tetrahydrofuran / 2.5 h / -78 - 0 °C

11.1: 74 percent / Grubbs' second generation catalyst / CH₂Cl₂ / 4 h / 25 °C

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium hydroxide; tetrabutyl ammonium fluoride; water; pyridinium trifluroacetate; sodium hydride; Dess-Martin periodane; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 4.1: Moffatt method / 10.1: Wittig reaction;
DOI:10.1016/S0040-4039(02)01926-3