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

Base Information

Chemical Name:5-bromo-1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(3-hydroxy-prop-1-ynyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-1H-pyrimidine-2,4-dione
CAS No.:223637-92-1
Molecular Formula:C₂₆H₃₅BrN₂O₇Si
Molecular Weight:595.563
Hs Code.:

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

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

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

There total 5 articles about 5-bromo-1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(3-hydroxy-prop-1-ynyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-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: 52.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 223637-86-3
1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(2,2-dibromo-vinyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-1H-pyrimidine-2,4-dione

: 223637-92-1
5-bromo-1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(3-hydroxy-prop-1-ynyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-1H-pyrimidine-2,4-dione

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; -78 deg C, 30 min then 0 deg C to r.t., 2 h;
DOI:10.1016/S0040-4039(99)00483-9

Reference yield:

: 88023-78-3
para-methoxybenzyl chloride

: 223637-92-1
5-bromo-1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(3-hydroxy-prop-1-ynyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 5 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

With oxalyl dichloride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; 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

: 223637-92-1
5-bromo-1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(3-hydroxy-prop-1-ynyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 2 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

With triethylamine; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1016/S0040-4039(99)00483-9