(2S,3R)-benzyl N⁵-benzyloxycarbonylamino-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate

Base Information

• Chemical Name: (2S,3R)-benzyl N⁵-benzyloxycarbonylamino-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate
• CAS No.: 116181-65-8
• Molecular Formula: C₂₃H₂₆N₂O₆
• Molecular Weight: 426.469

Synonyms:(2S,3R)-benzyl N⁵-benzyloxycarbonylamino-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate

Chemical Property of (2S,3R)-benzyl N⁵-benzyloxycarbonylamino-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate

Chemical Property:

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Technology Process of (2S,3R)-benzyl N⁵-benzyloxycarbonylamino-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate

There total 21 articles about (2S,3R)-benzyl N⁵-benzyloxycarbonylamino-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: 65.0%

erythro-N5-benzyloxycarbonyl-N2-(2-carboxyethyl)-3-hydroxyornithine benzyl ester (116181-64-7,130795-78-7) → erythro-benzyl 5-benzyloxycarbonylamino-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate (114342-11-9,114342-12-0,114358-85-9,116181-65-8,130795-79-8)

Guidance literature:

With 2,2'-dipyridyldisulphide; triphenylphosphine; In acetonitrile; Heating;

DOI:10.1039/P19900001521

Reference yield: 51.0%

(2S,3R)-N5-benzyloxycarbonyl-N2-(2-carboxyethyl)-3-hydroxyornithine benzyl ester (116181-64-7) → (2S,3R)-benzyl N5-benzyloxycarbonylamino-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate (116181-65-8)

Guidance literature:

With 2,2'-dipyridyldisulphide; triphenylphosphine; In acetonitrile; for 7.5h; Heating;

DOI:10.1039/P19900001521

Reference yield:

benzyl (2R,3R)-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(2-'oxoazetidin-1'-yl)pentanoate (865487-55-4) → (2S,3R)-benzyl N5-benzyloxycarbonylamino-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate (116181-65-8)

Guidance literature:

With 2,6-dichloro-benzonitrile; In dichloromethane; for 1h;

DOI:10.1021/ja992649d

upstream raw materials:

3-[(benzyloxycarbonyl)amino]propanal

benzyl (2-oxo-azetidin-1-yl)acetate

glycine benzyl ester p-toluenesulfonic acid salt

benzyl (3-bromopropionamido)acetate

Downstream raw materials:

proclavaminic acid

proclavaminic acid

erythro-5-amino-3-hydroxy-2-(2-oxoazetidin-1-yl)valeric acid

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