(3R,4R)-cis-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

Base Information

• Chemical Name: (3R,4R)-cis-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
• CAS No.: 103173-99-5
• Molecular Formula: C₁₅H₁₈N₄O₄
• Molecular Weight: 318.332

Synonyms:(3R,4R)-cis-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

Chemical Property of (3R,4R)-cis-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

Chemical Property:

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Technology Process of (3R,4R)-cis-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

There total 3 articles about (3R,4R)-cis-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-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: 55.0%

azidoacetic acid potassium salt + (S)-4-[(Z)-2-(4-Methoxy-phenyl)-vinyl]-2,2-dimethyl-[1,3]dioxolane → (3R,4R)-cis-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (103173-99-5)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; triethylamine; In dichloromethane; -20 deg C then r.t. overnight;

DOI:10.1039/c39860000161

Reference yield:

N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine (103239-04-9) + azidoacetic acid potassium salt → (3R,4R)-cis-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (103173-99-5)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; triethylamine; In dichloromethane; Yield given; Ambient temperature;

DOI:10.1021/jo00253a013

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (3R,4R)-cis-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (103173-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / 1 h / 0 °C

2: 55 percent / cyanuric chloride, Et₃N / CH₂Cl₂ / -20 deg C then r.t. overnight

With 1,3,5-trichloro-2,4,6-triazine; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1039/c39860000161

upstream raw materials:

N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

(3R,4R)-3-azido-4-[(S)-1,2-dihydroxyethyl]-1-(4-methoxyphenyl)azetidin-2-one

(3R,4R)-cis-1-(p-anisyl)-3-amino-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

(2R,3R)-3-Azido-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid

(3R,4R)-cis-1-(p-anisyl)-3-azido-4-carbomethoxyazetidin-2-one

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