(3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-4-phenyl-azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-4-phenyl-azetidin-2-one
• CAS No.: 182155-24-4
• Molecular Formula: C₁₅H₂₃NO₂Si
• Molecular Weight: 277.439

Synonyms:(3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-4-phenyl-azetidin-2-one

Chemical Property of (3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-4-phenyl-azetidin-2-one

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Technology Process of (3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-4-phenyl-azetidin-2-one

There total 7 articles about (3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-4-phenyl-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: 100.0%

(3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-(1-methoxy-1-methyl-ethoxy)-4-phenyl-azetidin-2-one (182155-22-2) → (3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-4-phenyl-azetidin-2-one (182155-24-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1016/0040-4039(96)01420-7

Reference yield: 75.0%

ethylmagnesium bromide (925-90-6) + (S)-1-(tert-Butyl-dimethyl-silanyl)-4-phenyl-azetidine-2,3-dione (182155-26-6) → (3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-4-phenyl-azetidin-2-one (182155-24-4) + (3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-ethyl-3-hydroxy-4-phenyl-azetidin-2-one

Guidance literature:

In tetrahydrofuran; at -40 ℃; for 3h; Yields of byproduct given;

DOI:10.1016/0040-4039(96)01420-7

Reference yield: 68.0%

vinyl magnesium bromide (1826-67-1) + (S)-1-(tert-Butyl-dimethyl-silanyl)-4-phenyl-azetidine-2,3-dione (182155-26-6) → (3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-4-phenyl-azetidin-2-one (182155-24-4) + (3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-4-phenyl-3-vinyl-azetidin-2-one

Guidance literature:

In tetrahydrofuran; at -40 ℃; for 3h; Yields of byproduct given;

DOI:10.1016/0040-4039(96)01420-7

upstream raw materials:

ethylmagnesium bromide

(S)-1-(tert-Butyl-dimethyl-silanyl)-4-phenyl-azetidine-2,3-dione

vinyl magnesium bromide

phenylmagnesium bromide

Downstream raw materials:

(S)-1-(tert-Butyl-dimethyl-silanyl)-4-phenyl-azetidine-2,3-dione

(3R,4S)-1-tert-butoxycarbonyl-3-[(triethylsilyl)oxy]-4-(phenyl)-3-methylazetidinone

(3R,4S)-1-Benzoyl-3-methyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one

(3R,4S)-3-[(triethylsilyl)oxy]-4-(phenyl)-3-methyl-azetidinone

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