(3S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)aminoazetidin-2-one

Base Information

• Chemical Name: (3S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)aminoazetidin-2-one
• CAS No.: 199385-33-6
• Molecular Formula: C₁₉H₁₈N₂O₄
• Molecular Weight: 338.363
• Mol file: 199385-33-6.mol

Synonyms:(3S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)aminoazetidin-2-one

Chemical Property of (3S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)aminoazetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)aminoazetidin-2-one

There total 3 articles about (3S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)aminoazetidin-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: 59.0%

(3S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)-1-N-(propen-1-yl)aminoazetidin-2-one → (3S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)aminoazetidin-2-one (199385-33-6)

Guidance literature:

With potassium permanganate; In phosphate buffer; acetone; pH=7.5;

DOI:10.1055/s-2000-6260

Reference yield:

phenylacetyl chloride (103-80-0) → (3S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)aminoazetidin-2-one (199385-33-6)

Guidance literature:

Multi-step reaction with 3 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

With potassium permanganate; sodium hydride; sodium carbonate; In tetrahydrofuran; phosphate buffer; water; acetone; 1.1: Acylation / 2.1: Metallation / 2.2: Acylation / 3.1: Oxidation;

DOI:10.1055/s-2000-6260

Reference yield:

(S)-3-N-(Phenylacetoxy)-1-N-(propen-1-yl)aminoazetidin-2-one → (3S)-3-N-(Benzyloxycarbonyl)-3-N-(phenylacetoxy)aminoazetidin-2-one (199385-33-6)

Guidance literature:

Multi-step reaction with 2 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

With potassium permanganate; sodium hydride; In tetrahydrofuran; phosphate buffer; acetone; 1.1: Metallation / 1.2: Acylation / 2.1: Oxidation;

DOI:10.1055/s-2000-6260

upstream raw materials:

phenylacetyl chloride

Downstream raw materials:

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

(3S,4S)-4-acetoxy-3-phenylacetamido-1-tert-butyldi methylsilyl-azetidin-2-one

(2S-trans)-N-<2-(acetyloxy)-4-oxo-3-azetidinyl>benzeneacetamide

(1E,5R)-3-Phenylmethyl-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-7-one