(3S,4S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)amino-4-acetoxyazetidin-2-one

Base Information

Chemical Name:(3S,4S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)amino-4-acetoxyazetidin-2-one
CAS No.:269742-76-9
Molecular Formula:C₂₁H₂₀N₂O₆
Molecular Weight:396.4
Hs Code.:

Synonyms:(3S,4S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)amino-4-acetoxyazetidin-2-one

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Chemical Property of (3S,4S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)amino-4-acetoxyazetidin-2-one

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Technology Process of (3S,4S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)amino-4-acetoxyazetidin-2-one

There total 4 articles about (3S,4S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)amino-4-acetoxyazetidin-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: 63.0%

: 64-19-7,77671-22-8
acetic acid

: 199385-33-6
(3S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)aminoazetidin-2-one

: 269742-76-9
(3S,4S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)amino-4-acetoxyazetidin-2-one

Guidance literature:: With peracetic acid; sodium acetate; Ru-carbon; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1055/s-2000-6260

Reference yield:

: 103-80-0
phenylacetyl chloride

: 269742-76-9
(3S,4S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)amino-4-acetoxyazetidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: Na₂CO₃ / acetone; H₂O / 20 °C

2.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

2.2: 65 percent / tetrahydrofuran / 0.33 h / 20 °C

3.1: 59 percent / KMnO₄ / aq. phosphate buffer; acetone / pH 7.5

4.1: 63 percent / AcOOH; AcONa / 5 percent Ru/C / CH₂Cl₂ / 2 h / 20 °C

With peracetic acid; potassium permanganate; sodium acetate; sodium hydride; sodium carbonate; Ru-carbon; In tetrahydrofuran; phosphate buffer; dichloromethane; water; acetone; 1.1: Acylation / 2.1: Metallation / 2.2: Acylation / 3.1: Oxidation / 4.1: Acetoxylation;
DOI:10.1055/s-2000-6260

Reference yield:

: (S)-3-N-(Phenylacetoxy)-1-N-(propen-1-yl)aminoazetidin-2-one

: 269742-76-9
(3S,4S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)amino-4-acetoxyazetidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

1.2: 65 percent / tetrahydrofuran / 0.33 h / 20 °C

2.1: 59 percent / KMnO₄ / aq. phosphate buffer; acetone / pH 7.5

3.1: 63 percent / AcOOH; AcONa / 5 percent Ru/C / CH₂Cl₂ / 2 h / 20 °C

With peracetic acid; potassium permanganate; sodium acetate; sodium hydride; Ru-carbon; In tetrahydrofuran; phosphate buffer; dichloromethane; acetone; 1.1: Metallation / 1.2: Acylation / 2.1: Oxidation / 3.1: Acetoxylation;
DOI:10.1055/s-2000-6260