(3S,4R)-3-<(1R)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2-oxo-4-(2-propynyl)-1-azetidineacetic acid,(4-nitrophenyl)methyl ester

Base Information

• Chemical Name: (3S,4R)-3-<(1R)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2-oxo-4-(2-propynyl)-1-azetidineacetic acid,(4-nitrophenyl)methyl ester
• CAS No.: 139179-07-0
• Molecular Formula: C₂₃H₃₂N₂O₆Si
• Molecular Weight: 460.602
• Mol file: 139179-07-0.mol

Synonyms:(3S,4R)-3-<(1R)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2-oxo-4-(2-propynyl)-1-azetidineacetic acid,(4-nitrophenyl)methyl ester

Chemical Property of (3S,4R)-3-<(1R)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2-oxo-4-(2-propynyl)-1-azetidineacetic acid,(4-nitrophenyl)methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-<(1R)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2-oxo-4-(2-propynyl)-1-azetidineacetic acid,(4-nitrophenyl)methyl ester

There total 3 articles about (3S,4R)-3-<(1R)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2-oxo-4-(2-propynyl)-1-azetidineacetic acid,(4-nitrophenyl)methyl 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: 76.0%

4-nitrobenzyl chloride (619-73-8) + (3S,4R)-3-<(1R)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2-oxo-4-(2-propynyl)-1-azetidineacetic acid (139179-05-8) → (3S,4R)-3-<(1R)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2-oxo-4-(2-propynyl)-1-azetidineacetic acid,(4-nitrophenyl)methyl ester (139179-07-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)89561-2

Reference yield:

(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-<(1R)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2-oxo-4-(2-propynyl)-1-azetidineacetic acid,(4-nitrophenyl)methyl ester (139179-07-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 66.9 percent / zinc, diethylaluminum chloride / tetrahydrofuran; toluene / 0 degC, 2 h, room t., overnight

2: 90 percent / sodium hydride / tetrahydrofuran; dimethylformamide / Ambient temperature

3: 76 percent / dicyclohexylcarbodiimide, dimethylaminopyridine / tetrahydrofuran

With dmap; diethylaluminium chloride; sodium hydride; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)89561-2

Reference yield:

(3S,4R)-3-{(1R)-{[tert-butyl(dimethyl)silyl]oxo}ethyl-4-prop-2-yn-1-yl}azetidine-2-one (85254-20-2) → (3S,4R)-3-<(1R)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2-oxo-4-(2-propynyl)-1-azetidineacetic acid,(4-nitrophenyl)methyl ester (139179-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / sodium hydride / tetrahydrofuran; dimethylformamide / Ambient temperature

2: 76 percent / dicyclohexylcarbodiimide, dimethylaminopyridine / tetrahydrofuran

With dmap; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)89561-2

upstream raw materials:

4-nitrobenzyl chloride

(3S,4R)-3-<(1R)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2-oxo-4-(2-propynyl)-1-azetidineacetic acid

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

(3S,4R)-3-{(1R)-{[tert-butyl(dimethyl)silyl]oxo}ethyl-4-prop-2-yn-1-yl}azetidine-2-one

Downstream raw materials:

(3S,4R)-3-<(1R)-1-<<(1,1-dimethylethyl)-dimethylsilyl>oxy>ethyl>-2-oxo-4-<3-<(4-fluorophenyl)-sulfonyl>-2-iodo-2(E)-propenyl>-1-azetidineacetic acid,(4-nitrophenyl)methyl ester

(2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[1-(4-fluoro-benzenesulfonyl)-meth-(Z)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(4-fluoro-benzenesulfonylmethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(5R,6S)-3-<<4-(fluorophenyl)-sulfonyl>methyl>-6-<(1R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylic acid,(4-nitrophenyl)methyl ester