[(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2E)-ylidene]-acetic acid benzyl ester

Base Information

• Chemical Name: [(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2E)-ylidene]-acetic acid benzyl ester
• CAS No.: 868082-97-7
• Molecular Formula: C₂₀H₂₉NO₄Si
• Molecular Weight: 375.54

Synonyms:[(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2E)-ylidene]-acetic acid benzyl ester

Chemical Property of [(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2E)-ylidene]-acetic acid benzyl ester

Chemical Property:

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Technology Process of [(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2E)-ylidene]-acetic acid benzyl ester

There total 1 articles about [(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2E)-ylidene]-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: 54.0%

(3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone (86978-81-6) + benzyl diazoacetate (52267-51-3) → [(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2E)-ylidene]-acetic acid benzyl ester (868082-97-7) + [(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2Z)-ylidene]-acetic acid benzyl ester (868082-96-6)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jm0580510

Reference yield: 43.0%

[(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2E)-ylidene]-acetic acid benzyl ester (868082-97-7) + methanethiosulfonic acid S-methyl ester (2949-92-0,31761-75-8) → (E)-benzyl 2-{(S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-1-(methylthio)-4-oxoazetidin-2-ylidene}acetate (1339193-17-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/cmdc.201100282

Reference yield: 39.0%

[(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2E)-ylidene]-acetic acid benzyl ester (868082-97-7) + 3,5-dibenzyloxylbenzoyl chloride (28917-44-4) → [(S)-1-(3,5-Bis-benzyloxy-benzoyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2E)-ylidene]-acetic acid benzyl ester

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃;

DOI:10.1016/j.bmc.2005.06.041

upstream raw materials:

(3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone

benzyl diazoacetate

Downstream raw materials:

(E)-benzyl 2-((S)-3-((R)-1-hydroxyethyl)-1-(methylthio)-4-oxoazetidin-2-ylidene)acetate

(R)-1-((S,E)-2-[2-(benzyloxy)-2-oxoethylidene]-1-(methylthio)-4-oxoazetidin-3-yl)ethyl 4-hydroxybenzoate

(R)-1-{(S,E)-2-[2-(benzyloxy)-2-oxoethylidene]-1-(methylthio)-4-oxoazetidin-3-yl}ethyl 4-hydroxy-3,5-dimethoxybenzoate

(E)-benzyl 2-{(S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-1-(methylthio)-4-oxoazetidin-2-ylidene}acetate

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