syn-(2S,3R)-(+)-N-benzoyl-3-phenylisoserine ethyl ester

Base Information

• Chemical Name: syn-(2S,3R)-(+)-N-benzoyl-3-phenylisoserine ethyl ester
• CAS No.: 153433-81-9
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.353
• Mol file: 153433-81-9.mol

Synonyms:syn-(2S,3R)-(+)-N-benzoyl-3-phenylisoserine ethyl ester

Chemical Property of syn-(2S,3R)-(+)-N-benzoyl-3-phenylisoserine ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of syn-(2S,3R)-(+)-N-benzoyl-3-phenylisoserine ethyl ester

There total 7 articles about syn-(2S,3R)-(+)-N-benzoyl-3-phenylisoserine ethyl ester 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: 87.0%

(4R,5S)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid ethyl ester (870287-36-8) → syn-(2S,3R)-(+)-N-benzoyl-3-phenylisoserine ethyl ester (153433-81-9)

Guidance literature:

With hydrogenchloride; In ethanol; for 6h; Heating;

DOI:10.1021/jo0516077

Reference yield:

2-keto-3-(N-benzoyl-amino)-3-phenyl propionic acid ethyl ester (153433-79-5) → ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (153433-80-8) + syn-(2S,3R)-(+)-N-benzoyl-3-phenylisoserine ethyl ester (153433-81-9)

Guidance literature:

With chromium chloride; [Ru(DMF)nCl₂]2; hydrogen; (2S,4S)-2,4-bis(diphenylphosphino)pentane; In ethanol; dichloromethane; at 60 ℃; for 48h; under 22801.5 Torr; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.tetasy.2011.11.017

Reference yield:

2-keto-3-(N-benzoyl-amino)-3-phenyl propionic acid ethyl ester (153433-79-5) → anti-(2S,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester (153433-82-0) + ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (153433-80-8) + syn-(2S,3R)-(+)-N-benzoyl-3-phenylisoserine ethyl ester (153433-81-9) + anti-(2R,3R)-(+)-N-benzoyl-3-phenylisoserine ethyl ester

Guidance literature:

With potassium phosphate buffer; D-glucose; at 28 ℃; for 48h; Product distribution; Hansenula polymorpha SC 13865; cells of various microorganisms, var. reaction time;

DOI:10.1007/BF02546196

upstream raw materials:

2-keto-3-(N-benzoyl-amino)-3-phenyl propionic acid ethyl ester

(4R,5S)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid ethyl ester

ethyl (2S,3S)-3-phenyloxirane-2-carboxylate

1-benzamido-3-ethoxy-3-oxo-1-phenylprop-1-en-2-yl ethyl oxalate