(4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Base Information

Chemical Name:(4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
CAS No.:186459-35-8
Molecular Formula:C₂₀H₂₃NO₄S
Molecular Weight:373.473
Hs Code.:

Synonyms:(4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

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Chemical Property of (4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

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Technology Process of (4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

There total 8 articles about (4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl 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: 96.5%

: 144837-72-9
allyl (4R,5S,6S)-3-benzylthio-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

: 186459-35-8
(4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Guidance literature:: With ammonium fluoride; hydrogen fluoride; In N,N-dimethyl-formamide; at 20 ℃; for 72h;
DOI:10.1039/P19960002851

Reference yield:

: 93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2
(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid

: 186459-35-8
(4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: NaH / tetrahydrofuran / 1.) 10 deg C, 20 min, 2.) 25 deg C, 1 h

2: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -50 °C

3: aq. K₂CO₃ / tetrahydrofuran / 0.25 h / 25 °C

4: 79.1 percent / DCC, DMAP / benzene / 17 h / 25 °C

6: 96.5 percent / NH₄F*HF / dimethylformamide; various solvent(s) / 72 h / 20 °C

With dmap; ammonium fluoride; hydrogen fluoride; sodium hexamethyldisilazane; sodium hydride; potassium carbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;
DOI:10.1039/P19960002851

Reference yield:

: 107514-91-0
(3S,4R)-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<(tert-butyldimethylsilyl)oxy>carbonyl>ethyl>azetidin-2-one

: 186459-35-8
(4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -50 °C

2: aq. K₂CO₃ / tetrahydrofuran / 0.25 h / 25 °C

3: 79.1 percent / DCC, DMAP / benzene / 17 h / 25 °C

5: 96.5 percent / NH₄F*HF / dimethylformamide; various solvent(s) / 72 h / 20 °C

With dmap; ammonium fluoride; hydrogen fluoride; sodium hexamethyldisilazane; potassium carbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;
DOI:10.1039/P19960002851