benzyl (2R,3R,4'S)-[3'-2H₂,4,5-3H₂]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(4'-thiophenyl-2-'oxoazetidin-1'-yl)pentanoate

Base Information

• Chemical Name: benzyl (2R,3R,4'S)-[3'-2H₂,4,5-3H₂]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(4'-thiophenyl-2-'oxoazetidin-1'-yl)pentanoate
• CAS No.: 255399-01-0
• Molecular Formula: C₂₉H₃₀N₂O₆S
• Molecular Weight: 540.601

Synonyms:benzyl (2R,3R,4'S)-[3'-2H₂,4,5-3H₂]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(4'-thiophenyl-2-'oxoazetidin-1'-yl)pentanoate

Chemical Property of benzyl (2R,3R,4'S)-[3'-2H₂,4,5-3H₂]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(4'-thiophenyl-2-'oxoazetidin-1'-yl)pentanoate

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Technology Process of benzyl (2R,3R,4'S)-[3'-2H₂,4,5-3H₂]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(4'-thiophenyl-2-'oxoazetidin-1'-yl)pentanoate

There total 7 articles about benzyl (2R,3R,4'S)-[3'-2H₂,4,5-3H₂]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(4'-thiophenyl-2-'oxoazetidin-1'-yl)pentanoate 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: 19.0%

[2,3-3H]-N-benzyloxycarbonyl-3-aminopropanal (255398-96-0) + benzyl (4'S)-[3-2H2]-(4'-thiophenyl-2-'oxoazetidin-1'-yl) acetate (255399-00-9) → benzyl (2R,3R,4'S)-[3'-2H2,4,5-3H2]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(4'-thiophenyl-2-'oxoazetidin-1'-yl)pentanoate (255399-01-0)

Guidance literature:

benzyl (4'S)-[3-2H₂]-(4'-thiophenyl-2-'oxoazetidin-1'-yl) acetate; With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

[2,3-3H]-N-benzyloxycarbonyl-3-aminopropanal; In tetrahydrofuran; hexane; for 2h;

DOI:10.1021/ja992649d

Reference yield:

thiophenol (108-98-5) → benzyl (2R,3R,4'S)-[3'-2H2,4,5-3H2]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(4'-thiophenyl-2-'oxoazetidin-1'-yl)pentanoate (255399-01-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (+)-cinchonine / benzene / 41 h / 40 °C

2.1: LiHMDS / hexane; tetrahydrofuran / 0.83 h / -78 °C

2.2: hexane; tetrahydrofuran / 1.75 h / -78 - -20 °C

3.1: LHMDS / tetrahydrofuran; hexane / 2 h / -78 °C

3.2: 19 percent / hexane; tetrahydrofuran / 2 h

With lithium hexamethyldisilazane; Cinchonin; In tetrahydrofuran; hexane; benzene; 1.1: Substitution / 2.1: deprotonation / 2.2: Substitution / 3.1: Metallation / 3.2: Addition;

DOI:10.1021/ja992649d

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyl (2R,3R,4'S)-[3'-2H2,4,5-3H2]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(4'-thiophenyl-2-'oxoazetidin-1'-yl)pentanoate (255399-01-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aq. NaHCO₃ / dioxane / 3.75 h / 0 - 20 °C

2.1: Et₃N / tetrahydrofuran / 2 h / 0 °C

3.1: aq. sodium borohydride / tetrahydrofuran / 5 h / 0 °C

4.1: (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -78 °C

5.1: LHMDS / tetrahydrofuran; hexane / 2 h / -78 °C

5.2: 19 percent / hexane; tetrahydrofuran / 2 h

With sodium tetrahydroborate; oxalyl dichloride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; 1.1: Acylation / 2.1: Condensation / 3.1: Reduction / 4.1: Swern oxidation / 5.1: Metallation / 5.2: Addition;

DOI:10.1021/ja992649d

upstream raw materials:

[2,3-3H]-N-benzyloxycarbonyl-3-aminopropanal

benzyl (4'S)-[3-2H₂]-(4'-thiophenyl-2-'oxoazetidin-1'-yl) acetate

thiophenol

benzyl chloroformate

Downstream raw materials:

benzyl (2S,3R)-[3'-2H₂,4,5-3H₂]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(2-'oxoazetidin-1'-yl)pentanoate

benzyl (2R,3R)-[3'-2H₂,4,5-3H₂]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(2-'oxoazetidin-1'-yl)pentanoate

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