(2S,3R)-4-nitrobenzyl 5-(4-bromophenylsulphonylamino)-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate

Base Information

Chemical Name:(2S,3R)-4-nitrobenzyl 5-(4-bromophenylsulphonylamino)-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate
CAS No.:130677-11-1
Molecular Formula:C₂₁H₂₂BrN₃O₈S
Molecular Weight:556.391
Hs Code.:

Synonyms:

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Chemical Property of (2S,3R)-4-nitrobenzyl 5-(4-bromophenylsulphonylamino)-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate

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Technology Process of (2S,3R)-4-nitrobenzyl 5-(4-bromophenylsulphonylamino)-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate

There total 11 articles about (2S,3R)-4-nitrobenzyl 5-(4-bromophenylsulphonylamino)-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate 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:

: 114342-03-9
benzyl (2-oxo-azetidin-1-yl)acetate

: 130677-11-1
(2S,3R)-4-nitrobenzyl 5-(4-bromophenylsulphonylamino)-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate

Guidance literature:: Multi-step reaction with 5 steps

1: 1) lithium bis(trimethylsilyl)amide / 1) THF, -70 deg C, 15 min, 2) THF, -70 deg C, 2 h

2: 39 percent / 1,5-diazabicyclo<4.3.0>non-5-ene / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 78 percent / NaOH (1M) / H₂O / 5.5 h / 36 °C / protease subtilisin Carlsberg (EC 3.4.21.14) (400 units, pH 6.5)

4: hydrogen / 5percent Pd/C / ethanol; H₂O / Ambient temperature

5: 1) 0.5M - caesium carbonate / 1) THF - water, pH 8, 2) DMF, overnight

With sodium hydroxide; DBN; hydrogen; caesium carbonate; lithium hexamethyldisilazane; palladium on activated charcoal; In ethanol; dichloromethane; water;
DOI:10.1039/P19900001513

Reference yield:

: 114342-03-9
benzyl (2-oxo-azetidin-1-yl)acetate

: 130677-11-1,130793-35-0
threo-4-nitrobenzyl 5-(4-bromophenylsulphonylamino)-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate

Guidance literature:: Multi-step reaction with 4 steps

1: 1) lithium bis(trimethylsilyl)amide / 1) THF, -70 deg C, 15 min, 2) THF, -70 deg C, 2 h

2: 39 percent / 1,5-diazabicyclo<4.3.0>non-5-ene / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 99 percent / hydrogen / 5percent Pd/C / ethanol; H₂O / Ambient temperature

4: 1) 0.5M - caesium carbonate / 1) THF - water, pH 8, 2) DMF, overnight

With DBN; hydrogen; caesium carbonate; lithium hexamethyldisilazane; palladium on activated charcoal; In ethanol; dichloromethane; water;
DOI:10.1039/P19900001513

Reference yield:

: 130676-99-2
benzyl (3-bromopropionamido)acetate

: 130677-11-1,130793-35-0
threo-4-nitrobenzyl 5-(4-bromophenylsulphonylamino)-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate

Guidance literature:: Multi-step reaction with 5 steps

1: 38 percent / potassium hydroxide, tetrabutylammonium bromide / CH₂Cl₂; acetonitrile / 0.5 h

2: 1) lithium bis(trimethylsilyl)amide / 1) THF, -70 deg C, 15 min, 2) THF, -70 deg C, 2 h

3: 39 percent / 1,5-diazabicyclo<4.3.0>non-5-ene / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 99 percent / hydrogen / 5percent Pd/C / ethanol; H₂O / Ambient temperature

5: 1) 0.5M - caesium carbonate / 1) THF - water, pH 8, 2) DMF, overnight

With potassium hydroxide; DBN; tetrabutylammomium bromide; hydrogen; caesium carbonate; lithium hexamethyldisilazane; palladium on activated charcoal; In ethanol; dichloromethane; water; acetonitrile;
DOI:10.1039/P19900001513