(3S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-4-[(1Z)-2-oxo-2-phenylethylidene]azetidin-2-one

Base Information

• Chemical Name: (3S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-4-[(1Z)-2-oxo-2-phenylethylidene]azetidin-2-one
• CAS No.: 592528-33-1
• Molecular Formula: C₁₉H₂₇NO₃Si
• Molecular Weight: 345.514

Synonyms:(3S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-4-[(1Z)-2-oxo-2-phenylethylidene]azetidin-2-one

Chemical Property of (3S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-4-[(1Z)-2-oxo-2-phenylethylidene]azetidin-2-one

Chemical Property:

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Technology Process of (3S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-4-[(1Z)-2-oxo-2-phenylethylidene]azetidin-2-one

There total 2 articles about (3S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-4-[(1Z)-2-oxo-2-phenylethylidene]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: 55.0%

2-diazo-acetophenone (3282-32-4) + (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone (86978-81-6) → (3S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-4-[(1Z)-2-oxo-2-phenylethylidene]azetidin-2-one (592528-33-1)

Guidance literature:

(3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone; With chloro-trimethyl-silane; triethylamine; In dichloromethane; at 20 ℃;

2-diazo-acetophenone; With titanium tetrachloride; In dichloromethane; at 20 ℃; for 3h; Further stages.;

DOI:10.1002/ejoc.200210702

Reference yield: 20.0%

(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) + 2-diazo-acetophenone (3282-32-4) → (3S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-4-[(1Z)-2-oxo-2-phenylethylidene]azetidin-2-one (592528-33-1)

Guidance literature:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one; With chloro-trimethyl-silane; triethylamine; In dichloromethane; at 20 ℃;

2-diazo-acetophenone; With titanium tetrachloride; In dichloromethane; at 20 ℃; for 3h; Further stages.;

DOI:10.1002/ejoc.200210702

Reference yield:

<2-(trimethylsilyl)ethyl>oxalyl chloride (109862-07-9) + (3S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-4-[(1Z)-2-oxo-2-phenylethylidene]azetidin-2-one (592528-33-1) → {(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-[2-oxo-2-phenyl-eth-(Z)-ylidene]-azetidin-1-yl}-oxo-acetic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:

In benzene; Heating;

DOI:10.1016/S0040-4039(03)01533-8

upstream raw materials:

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

2-diazo-acetophenone

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

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