{(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidin-1-yl}-acetic acid benzyl ester

Base Information

• Chemical Name: {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidin-1-yl}-acetic acid benzyl ester
• CAS No.: 828942-68-3
• Molecular Formula: C₂₂H₃₃NO₄Si
• Molecular Weight: 403.594
• Mol file: 828942-68-3.mol

Synonyms:{(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidin-1-yl}-acetic acid benzyl ester

Chemical Property of {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidin-1-yl}-acetic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidin-1-yl}-acetic acid benzyl ester

There total 1 articles about {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidin-1-yl}-acetic acid benzyl ester 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: 83.0%

(3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-vinyl-2-azetidinone (112256-72-1) + Benzyl bromoacetate (5437-45-6) → {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidin-1-yl}-acetic acid benzyl ester (828942-68-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.tetasy.2004.10.021

Reference yield: 100.0%

carbon monoxide (201230-82-2) + {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidin-1-yl}-acetic acid benzyl ester (828942-68-3) → [(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-(3-oxo-propyl)-azetidin-1-yl]-acetic acid benzyl ester

Guidance literature:

With (2,5-norbornadiene)Rh⁺B^-Ph₄; chiral binaphthyl-based phosphine ligand; hydrogen; In benzene; at 60 ℃; for 90h; under 45600 Torr;

DOI:10.1016/j.tetasy.2004.10.021

Reference yield:

carbon monoxide (201230-82-2) + {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidin-1-yl}-acetic acid benzyl ester (828942-68-3) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((S)-1-methyl-2-oxo-ethyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester + [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-1-methyl-2-oxo-ethyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester + [(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-(3-oxo-propyl)-azetidin-1-yl]-acetic acid benzyl ester

Guidance literature:

With (2,5-norbornadiene)Rh⁺B^-Ph₄; chiral binaphthyl-based phosphine ligand; hydrogen; In benzene; at 60 ℃; for 90h; under 45600 Torr; Title compound not separated from byproducts;

DOI:10.1016/j.tetasy.2004.10.021

upstream raw materials:

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

Benzyl bromoacetate