(E)-S-phenyl 3-((2R,3S,5R)-3-(tert-butyldimethylsilyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate

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Chemical Name:(E)-S-phenyl 3-((2R,3S,5R)-3-(tert-butyldimethylsilyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate
CAS No.:911826-90-9
Molecular Formula:C₂₄H₃₂N₂O₅SSi
Molecular Weight:488.68
Hs Code.:

Synonyms:(E)-S-phenyl 3-((2R,3S,5R)-3-(tert-butyldimethylsilyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate

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Chemical Property of (E)-S-phenyl 3-((2R,3S,5R)-3-(tert-butyldimethylsilyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate

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Technology Process of (E)-S-phenyl 3-((2R,3S,5R)-3-(tert-butyldimethylsilyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate

There total 2 articles about (E)-S-phenyl 3-((2R,3S,5R)-3-(tert-butyldimethylsilyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate 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%

: 73818-39-0
(Triphenylphosphoranyliden)thioessigsaeure-S-phenylester

: 131118-61-1
3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde

: 911826-90-9
(E)-S-phenyl 3-((2R,3S,5R)-3-(tert-butyldimethylsilyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate

Guidance literature:: In toluene; at 20 ℃; for 48h;
DOI:10.1016/j.tetlet.2004.04.011

Reference yield:

: 40733-27-5
3'-O-(t-butyldimethylsilyl)thymidine

: 911826-90-9
(E)-S-phenyl 3-((2R,3S,5R)-3-(tert-butyldimethylsilyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate

Guidance literature:: Multi-step reaction with 2 steps

1: Dess-Martin reagent / CH₂Cl₂ / 0 - 20 °C

2: 3.61 g / toluene / 48 h / 20 °C

With Dess-Martin periodane; In dichloromethane; toluene; 2: Wittig reaction;
DOI:10.1021/jm060471h

Reference yield:

: 911826-90-9
(E)-S-phenyl 3-((2R,3S,5R)-3-(tert-butyldimethylsilyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-2-yl)prop-2-enethioate

: 1-((2R,4S,5S)-4-hydroxy-5-((S)-[5-(2,5-dioxo-1,2-dithiolan-3-yl)]-tetrahydrofuran-2-yl))-5-methylpyrimidine-2,4(1H,3H)-dione

Guidance literature:: Multi-step reaction with 4 steps

1: H₂S(gas); Et₃N / dioxane / 2 h / 20 °C

2: 0.591 g / K₃[Fe(CN)6] / dioxane; H₂O / 16 h

3: 95 percent / aq. TFA / tetrahydrofuran / 6 h / 0 °C

4: 95 percent / dimethyldioxirane / acetone / 2 h

With hydrogen sulfide; 3,3-dimethyldioxirane; triethylamine; trifluoroacetic acid; potassium hexacyanoferrate(III); In tetrahydrofuran; 1,4-dioxane; water; acetone;
DOI:10.1021/jm060471h