[(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]-acetic acid tert-butyl ester

Base Information

Chemical Name:[(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]-acetic acid tert-butyl ester
CAS No.:185556-99-4
Molecular Formula:C₂₁H₂₆N₂O₇S
Molecular Weight:450.513
Hs Code.:

[(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]-acetic acid tert-butyl ester

Synonyms:[(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]-acetic acid tert-butyl ester

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Chemical Property of [(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]-acetic acid tert-butyl ester

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Technology Process of [(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]-acetic acid tert-butyl ester

There total 1 articles about [(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]-acetic acid tert-butyl ester 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: 95.0%

: 185556-93-8
[(2R,3R,3aR,9aR)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-3-phenylsulfanyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl]-acetic acid tert-butyl ester

: 185556-99-4
[(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]-acetic acid tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/jo9613601

Reference yield: 91.0%

: 13154-24-0
triisopropylsilyl chloride

: 185556-99-4
[(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]-acetic acid tert-butyl ester

: 185557-00-0
[(2R,3R,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-phenylsulfanyl-5-triisopropylsilanyloxymethyl-tetrahydro-furan-3-yl]-acetic acid tert-butyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 24h; Ambient temperature;
DOI:10.1021/jo9613601

Reference yield:

: 185556-99-4
[(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]-acetic acid tert-butyl ester

: 185556-84-7
1-((3aS,4R,6R,6aR)-2-Oxo-3a-phenylsulfanyl-6-triisopropylsilanyloxymethyl-hexahydro-furo[3,4-b]furan-4-yl)-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

2: 90 percent / mCPBA / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) room temp., 10 h

3: LiSPh / tetrahydrofuran / 20 h / Ambient temperature

With 1H-imidazole; lithium thiophenoxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo9613601