2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-methyl-thiopropionic acid S-p-tolyl ester

Base Information

• Chemical Name: 2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-methyl-thiopropionic acid S-p-tolyl ester
• CAS No.: 101765-72-4
• Molecular Formula: C₂₂H₃₅NO₃SSi
• Molecular Weight: 421.676
• Mol file: 101765-72-4.mol

Synonyms:

Chemical Property of 2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-methyl-thiopropionic acid S-p-tolyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-methyl-thiopropionic acid S-p-tolyl ester

There total 1 articles about 2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-methyl-thiopropionic acid S-p-tolyl 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: 46.0%

Trimethyl-(2-methyl-1-p-tolylsulfanyl-propenyloxy)-silane (101765-68-8) + Acetic acid (2R,3R)-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester (86978-81-6,87392-17-4,92217-75-9) → 2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-methyl-thiopropionic acid S-p-tolyl ester (101765-72-4)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In dichloromethane; Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4039(00)94938-4

Reference yield:

2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-methyl-thiopropionic acid S-p-tolyl ester (101765-72-4) → (2R,5S,6S)-6-(1-Hydroxy-ethyl)-4,4-dimethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (78270-60-7,86420-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / methanol

2: according to the Merck method

With sodium hydroxide; In methanol;

DOI:10.1016/S0040-4039(00)94938-4

Reference yield:

2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-methyl-thiopropionic acid S-p-tolyl ester (101765-72-4) → (S)-3-{2-[(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-nitro-benzyloxyoxalyl)-4-oxo-azetidin-2-yl]-2-methyl-propionylsulfanyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Guidance literature:

applied Oida's method;

DOI:10.1016/S0040-4039(00)94938-4

upstream raw materials:

Trimethyl-(2-methyl-1-p-tolylsulfanyl-propenyloxy)-silane

Acetic acid (2R,3R)-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester

Downstream raw materials:

(2R,5S,6S)-6-(1-Hydroxy-ethyl)-4,4-dimethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester