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

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Chemical Name:(3R,4S)-1-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-hydroxyazetidin-2-one
CAS No.:213480-22-9
Molecular Formula:C₁₇H₂₂N₂O₆
Molecular Weight:350.371
Hs Code.:

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

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

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

There total 6 articles about (3R,4S)-1-benzyl-4-[(1S,5S)-5-carbamoyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-hydroxyazetidin-2-one 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: 91.0%

: 213480-21-8
Carbamic acid (4S,5S)-5-((2S,3R)-1-benzyl-3-benzyloxy-4-oxo-azetidin-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

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

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 16h; under 760 Torr;
DOI:10.1021/jo980354x

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; ammonium hydroxide; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 1: Condensation / 2: Cycloaddition / 3: Hydrogenolysis / 4: Esterification / 5: ammonolysis / 6: Hydrogenolysis;
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

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

Guidance literature:: Multi-step reaction with 4 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

With pyridine; ammonium hydroxide; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 1: Hydrogenolysis / 2: Esterification / 3: ammonolysis / 4: Hydrogenolysis;
DOI:10.1021/jo980354x