(4S)-3-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]oxazolidine-3,5-dione

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Chemical Name:(4S)-3-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]oxazolidine-3,5-dione
CAS No.:213480-23-0
Molecular Formula:C₁₇H₂₀N₂O₇
Molecular Weight:364.355
Hs Code.:

Synonyms:(4S)-3-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]oxazolidine-3,5-dione

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Chemical Property of (4S)-3-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]oxazolidine-3,5-dione

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Technology Process of (4S)-3-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]oxazolidine-3,5-dione

There total 7 articles about (4S)-3-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]oxazolidine-3,5-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: 90.0%

: 213480-22-9
(3R,4S)-1-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-hydroxyazetidin-2-one

: 213480-23-0
(4S)-3-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]oxazolidine-3,5-dione

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; In phosphate buffer; dichloromethane; at -5 - 0 ℃; pH=7;
DOI:10.1021/jo980354x

Reference yield:

: 81028-12-8
(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

: 213480-23-0
(4S)-3-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]oxazolidine-3,5-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 4A MS / CH₂Cl₂ / 1 h / 0 °C

2: 8.29 g / triethylamine / CH₂Cl₂ / -78 - 20 °C

3: 95 percent / hydrogen / Pd/C / methanol / 20 °C / 760 Torr

4: pyridine / CH₂Cl₂ / 0.75 h / 0 - 20 °C

5: 9.95 g / aq. NH₃ / tetrahydrofuran / 0.5 h / 0 - 20 °C

6: 91 percent / hydrogen / Pd/C / methanol / 16 h / 20 °C / 760 Torr

7: 90 percent / sodium hypochlorite; 2,2,6,6-tetramethylpiperidin-1-oxyl; potassium bromide / CH₂Cl₂; aq. phosphate buffer / -5 - 0 °C / pH 7

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; ammonium hydroxide; sodium hypochlorite; hydrogen; triethylamine; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; dichloromethane; 1: Condensation / 2: Cycloaddition / 3: Hydrogenolysis / 4: Esterification / 5: ammonolysis / 6: Hydrogenolysis / 7: Oxidation;
DOI:10.1021/jo980354x

Reference yield:

: 190007-79-5
(3R,4S)-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-benzyloxyazetidin-2-one

: 213480-23-0
(4S)-3-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]oxazolidine-3,5-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / hydrogen / Pd/C / methanol / 20 °C / 760 Torr

2: pyridine / CH₂Cl₂ / 0.75 h / 0 - 20 °C

3: 9.95 g / aq. NH₃ / tetrahydrofuran / 0.5 h / 0 - 20 °C

4: 91 percent / hydrogen / Pd/C / methanol / 16 h / 20 °C / 760 Torr

5: 90 percent / sodium hypochlorite; 2,2,6,6-tetramethylpiperidin-1-oxyl; potassium bromide / CH₂Cl₂; aq. phosphate buffer / -5 - 0 °C / pH 7

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; ammonium hydroxide; sodium hypochlorite; hydrogen; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; dichloromethane; 1: Hydrogenolysis / 2: Esterification / 3: ammonolysis / 4: Hydrogenolysis / 5: Oxidation;
DOI:10.1021/jo980354x