[(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-phenylsulfanyl-tetrahydro-furan-3-yl]-acetonitrile

Base Information

Chemical Name:[(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-phenylsulfanyl-tetrahydro-furan-3-yl]-acetonitrile
CAS No.:180896-08-6
Molecular Formula:C₂₃H₃₁N₃O₅SSi
Molecular Weight:489.668
Hs Code.:

[(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-phenylsulfanyl-tetrahydro-furan-3-yl]-acetonitrile

Synonyms:[(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-phenylsulfanyl-tetrahydro-furan-3-yl]-acetonitrile

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Chemical Property of [(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-phenylsulfanyl-tetrahydro-furan-3-yl]-acetonitrile

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Technology Process of [(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-phenylsulfanyl-tetrahydro-furan-3-yl]-acetonitrile

There total 5 articles about [(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-phenylsulfanyl-tetrahydro-furan-3-yl]-acetonitrile 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: 86.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 180896-09-7
[(2R,3R,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-3-phenylsulfanyl-tetrahydro-furan-3-yl]-acetonitrile

: 180896-08-6
[(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-phenylsulfanyl-tetrahydro-furan-3-yl]-acetonitrile

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 14h; Ambient temperature;
DOI:10.1021/jo960577s

Reference yield:

: 84828-97-7
1-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione

: 180896-08-6
[(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-phenylsulfanyl-tetrahydro-furan-3-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / CH₂Cl₂; tetrahydrofuran / 3 h / Ambient temperature

2: 59 percent / PhSH / tetrahydrofuran / 3 h / Ambient temperature

3: 71 percent / NH₄F / methanol / 2 h / 65 °C

4: 86 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

With 1H-imidazole; ammonium fluoride; thiophenol; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo960577s

Reference yield:

: 2973-86-6
lithium thiophenoxide

: 180896-08-6
[(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-phenylsulfanyl-tetrahydro-furan-3-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 3 steps

1: 59 percent / PhSH / tetrahydrofuran / 3 h / Ambient temperature

2: 71 percent / NH₄F / methanol / 2 h / 65 °C

3: 86 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

With 1H-imidazole; ammonium fluoride; thiophenol; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo960577s