p-nitrobenzyl (2R)- and (2S)-2-<(3S,4R)-4-methylthio-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>-4,4-dimethyl-3-oxopentanoates

Base Information

Chemical Name:p-nitrobenzyl (2R)- and (2S)-2-<(3S,4R)-4-methylthio-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>-4,4-dimethyl-3-oxopentanoates
CAS No.:146039-57-8
Molecular Formula:C₂₇H₂₉N₃O₁₁S
Molecular Weight:603.607
Hs Code.:

p-nitrobenzyl (2R)- and (2S)-2-<(3S,4R)-4-methylthio-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>-4,4-dimethyl-3-oxopentanoates

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Chemical Property of p-nitrobenzyl (2R)- and (2S)-2-<(3S,4R)-4-methylthio-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>-4,4-dimethyl-3-oxopentanoates

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Technology Process of p-nitrobenzyl (2R)- and (2S)-2-<(3S,4R)-4-methylthio-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>-4,4-dimethyl-3-oxopentanoates

There total 5 articles about p-nitrobenzyl (2R)- and (2S)-2-<(3S,4R)-4-methylthio-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>-4,4-dimethyl-3-oxopentanoates 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: 80.0%

: 3282-30-2
pivaloyl chloride

: 146142-28-1
p-nitrobenzyl (-)-(3S,4R)-<4-methylthio-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>acetate

: 146039-57-8,146142-29-2
p-nitrobenzyl (2R)- and (2S)-2-<(3S,4R)-4-methylthio-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>-4,4-dimethyl-3-oxopentanoates

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -75 ℃; for 0.5h;
DOI:10.1055/s-1992-26329

Reference yield:

: 87154-05-0
(+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane

: 146039-57-8,146142-29-2
p-nitrobenzyl (2R)- and (2S)-2-<(3S,4R)-4-methylthio-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>-4,4-dimethyl-3-oxopentanoates

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / m-chloroperbenzoic acid (MCPBA) / CH₂Cl₂ / 4.5 h / -5 - 5 °C

2: 75 percent / aq. AcOH / 2.5 h / Heating

3: 75 percent / acetonitrile; H₂O / 0.67 h / 0 °C

4: 70 percent / Cs₂CO₃ / acetonitrile / 4 h / 0 °C

5: 80 percent / lithium bisamide / tetrahydrofuran / 0.5 h / -75 °C

With caesium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1055/s-1992-26329

Reference yield:

: 87154-03-8
(+)-(3S,4R)-4-<(2R)-2-(1-hydroxypropyl)-sulfonyl>-3-(p-nitrobenzyloxycarbonyloxymethyl)azetidin-2-one

: 146039-57-8,146142-29-2
p-nitrobenzyl (2R)- and (2S)-2-<(3S,4R)-4-methylthio-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>-4,4-dimethyl-3-oxopentanoates

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / acetonitrile; H₂O / 0.67 h / 0 °C

2: 70 percent / Cs₂CO₃ / acetonitrile / 4 h / 0 °C

3: 80 percent / lithium bisamide / tetrahydrofuran / 0.5 h / -75 °C

With caesium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; water; acetonitrile;
DOI:10.1055/s-1992-26329