(S)-3-Benzyl-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxazolidine-2,5-dione

Base Information

Chemical Name:(S)-3-Benzyl-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxazolidine-2,5-dione
CAS No.:260354-45-8
Molecular Formula:C₂₂H₂₃NO₆
Molecular Weight:397.428
Hs Code.:

Synonyms:(S)-3-Benzyl-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxazolidine-2,5-dione

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Chemical Property of (S)-3-Benzyl-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxazolidine-2,5-dione

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Technology Process of (S)-3-Benzyl-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxazolidine-2,5-dione

There total 8 articles about (S)-3-Benzyl-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxazolidine-2,5-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: 98.0%

: 260354-43-6
(3R,4R)-1-Benzyl-3-hydroxy-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-azetidin-2-one

: 260354-45-8
(S)-3-Benzyl-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxazolidine-2,5-dione

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; In phosphate buffer; dichloromethane; water; at 0 ℃; for 3h; pH=7.0;
DOI:10.1021/jo990964c

Reference yield:

: 1025887-95-9
Benzyl-[1-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-meth-(E)-ylidene]-amine

: 260354-45-8
(S)-3-Benzyl-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxazolidine-2,5-dione

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 91 percent / H₂ / Pd/C / methanol / 16 h / 20 °C / 760.05 Torr

3: 98 percent / TEMPO; KBr; NaOCl / CH₂Cl₂; H₂O; aq. phosphate buffer / 3 h / 0 °C / pH 7.0

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; hydrogen; triethylamine; potassium bromide; palladium on activated charcoal; In methanol; phosphate buffer; dichloromethane; water; 1: Cycloaddition / 2: Hydrogenation / 3: cycloexpansion;
DOI:10.1021/jo990964c

Reference yield:

: 122517-81-1
(2R,3S)-methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate

: 260354-45-8
(S)-3-Benzyl-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxazolidine-2,5-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / p-TsOH*H₂O / benzene / 1 h / Heating

2: DIBAL / toluene / 2 h / -78 °C

3: CH₂Cl₂ / 1 h / 0 °C

4: Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 91 percent / H₂ / Pd/C / methanol / 16 h / 20 °C / 760.05 Torr

6: 98 percent / TEMPO; KBr; NaOCl / CH₂Cl₂; H₂O; aq. phosphate buffer / 3 h / 0 °C / pH 7.0

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; potassium bromide; palladium on activated charcoal; In methanol; phosphate buffer; dichloromethane; water; toluene; benzene; 1: Cycloaddition / 2: Reduction / 3: Condensation / 4: Cycloaddition / 5: Hydrogenation / 6: cycloexpansion;
DOI:10.1021/jo990964c