(3S,4R)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-azetidin-2-one

Base Information

• Chemical Name: (3S,4R)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-azetidin-2-one
• CAS No.: 256371-18-3
• Molecular Formula: C₂₀H₃₁NO₂Si
• Molecular Weight: 345.557
• Mol file: 256371-18-3.mol

Synonyms:(3S,4R)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-azetidin-2-one

Chemical Property of (3S,4R)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-azetidin-2-one

There total 6 articles about (3S,4R)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-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: 96.0%

benzyl bromide (100-39-0) + (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-vinyl-2-azetidinone (112256-72-1) → (3S,4R)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-azetidin-2-one (256371-18-3)

Guidance literature:

(3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-vinyl-2-azetidinone; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; at -78 ℃; for 6h;

DOI:10.1021/ja993080j

Reference yield:

(3S,4S)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-ethynyl-azetidin-2-one (108053-21-0) → (3S,4R)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-azetidin-2-one (256371-18-3)

Guidance literature:

With hydrogen; Lindlar catalyst; In Petroleum ether;

DOI:10.1016/S0040-4039(00)84472-X

Reference yield:

N-<3-(trimethylsilyl)-2-propynylidene>benzylamine (101911-11-9) → (3S,4R)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-azetidin-2-one (256371-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 55 percent

2: 1.) KOH, H₂O, 2.) (PyS)2-Ph₃P / 1.) THF, 2.) CH₃CN

3: imidazole / dimethylformamide

4: H₂ / Lindlar cat. / petroleum ether

With 1H-imidazole; potassium hydroxide; water; hydrogen; triphenylphosphine; Lindlar catalyst; In N,N-dimethyl-formamide; Petroleum ether;

DOI:10.1016/S0040-4039(00)84472-X

upstream raw materials:

(3S,4S)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-ethynyl-azetidin-2-one

benzyl bromide

(3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-vinyl-2-azetidinone

N-<3-(trimethylsilyl)-2-propynylidene>benzylamine

Downstream raw materials:

(3S,4R)-1-Benzyl-4-(2-benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one

(3S,4R)-1-Benzyl-3-((R)-1-methoxy-ethyl)-4-vinyl-azetidin-2-one