(3S,4R)-3-[(R)-1-(t-butyldimethylsiloxy)ethyl]-4-[(R)-1-(2-hydroxybenzoyl)ethyl]-2-azetidinone

Base Information

• Chemical Name: (3S,4R)-3-[(R)-1-(t-butyldimethylsiloxy)ethyl]-4-[(R)-1-(2-hydroxybenzoyl)ethyl]-2-azetidinone
• CAS No.: 175417-05-7
• Molecular Formula: C₂₀H₃₁NO₄Si
• Molecular Weight: 377.556
• Mol file: 175417-05-7.mol

Synonyms:(3S,4R)-3-[(R)-1-(t-butyldimethylsiloxy)ethyl]-4-[(R)-1-(2-hydroxybenzoyl)ethyl]-2-azetidinone

Chemical Property of (3S,4R)-3-[(R)-1-(t-butyldimethylsiloxy)ethyl]-4-[(R)-1-(2-hydroxybenzoyl)ethyl]-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-[(R)-1-(t-butyldimethylsiloxy)ethyl]-4-[(R)-1-(2-hydroxybenzoyl)ethyl]-2-azetidinone

There total 2 articles about (3S,4R)-3-[(R)-1-(t-butyldimethylsiloxy)ethyl]-4-[(R)-1-(2-hydroxybenzoyl)ethyl]-2-azetidinone 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: 78.0%

1-(2-Hydroxy-phenyl)-propan-1-on (610-99-1) + (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → (3S,4R)-3-[(R)-1-(t-butyldimethylsiloxy)ethyl]-4-[(R)-1-(2-hydroxybenzoyl)ethyl]-2-azetidinone (175417-05-7)

Guidance literature:

1-(2-Hydroxy-phenyl)-propan-1-on; With tributyl-amine; titanium tetrachloride; In dichloromethane; at -78 - -40 ℃; for 1h;

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one; In dichloromethane; at -20 ℃; for 10h; Further stages.;

DOI:10.1016/j.tet.2003.11.048

Reference yield:

1-(2-Hydroxy-phenyl)-propan-1-on (610-99-1) + (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(S)-2-(2-hydroxy-phenyl)-1-methyl-2-oxo-ethyl]-azetidin-2-one + (3S,4R)-3-[(R)-1-(t-butyldimethylsiloxy)ethyl]-4-[(R)-1-(2-hydroxybenzoyl)ethyl]-2-azetidinone (175417-05-7)

Guidance literature:

1-(2-Hydroxy-phenyl)-propan-1-on; With tributyl-amine; titanium tetrachloride; In dichloromethane; at -78 - -40 ℃; for 1h;

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one; In dichloromethane; at -20 ℃; for 10h; Further stages. Title compound not separated from byproducts.;

DOI:10.1016/j.tet.2003.11.048

Reference yield: 60.0%

(3S,4R)-3-[(R)-1-(t-butyldimethylsiloxy)ethyl]-4-[(R)-1-(2-hydroxybenzoyl)ethyl]-2-azetidinone (175417-05-7) → (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid (93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2)

Guidance literature:

With silica gel; ozone; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/j.tet.2003.11.048

upstream raw materials:

1-(2-Hydroxy-phenyl)-propan-1-on

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

Downstream raw materials:

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid