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

Base Information

• Chemical Name: benzyl (2R,3R)-[3'-2H₂,4,5-3H₂]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(2-'oxoazetidin-1'-yl)pentanoate
• CAS No.: 255399-02-1
• Molecular Formula: C₂₃H₂₆N₂O₆
• Molecular Weight: 432.437

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

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

Chemical Property:

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

There total 7 articles about benzyl (2R,3R)-[3'-2H₂,4,5-3H₂]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(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: 82.0%

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) → benzyl (2R,3R)-[3'-2H2,4,5-3H2]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(2-'oxoazetidin-1'-yl)pentanoate (255399-02-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; In benzene; for 16.5h; Heating;

DOI:10.1021/ja992649d

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyl (2R,3R)-[3'-2H2,4,5-3H2]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(2-'oxoazetidin-1'-yl)pentanoate (255399-02-1)

Guidance literature:

Multi-step reaction with 6 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

6.1: 82 percent / tris(trimethylsilyl)silyl hydride; AIBN / benzene / 16.5 h / Heating

With sodium tetrahydroborate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; benzene; 1.1: Acylation / 2.1: Condensation / 3.1: Reduction / 4.1: Swern oxidation / 5.1: Metallation / 5.2: Addition / 6.1: Reduction;

DOI:10.1021/ja992649d

Reference yield:

[2,3-3H]-N-benzyloxycarbonyl-3-aminopropanal (255398-96-0) → benzyl (2R,3R)-[3'-2H2,4,5-3H2]-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(2-'oxoazetidin-1'-yl)pentanoate (255399-02-1)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 19 percent / hexane; tetrahydrofuran / 2 h

2.1: 82 percent / tris(trimethylsilyl)silyl hydride; AIBN / benzene / 16.5 h / Heating

With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; benzene; 1.1: Metallation / 1.2: Addition / 2.1: Reduction;

DOI:10.1021/ja992649d

upstream raw materials:

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

benzyl chloroformate

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

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

Downstream raw materials:

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

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