anti-(2S,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester

Base Information

• Chemical Name: anti-(2S,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester
• CAS No.: 153433-82-0
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.353
• Mol file: 153433-82-0.mol

Synonyms:anti-(2S,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester

Chemical Property of anti-(2S,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of anti-(2S,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester

There total 18 articles about anti-(2S,3S)-(-)-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: 97.0%

C18H17NO4 → anti-(2S,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester (153433-82-0)

Guidance literature:

C₁₈H₁₇NO₄; With trichlorosilane; C₁₉H₂₁N₃O₇S; benzoic acid; In dichloromethane; at -40 ℃; for 72h;

With potassium carbonate; In dichloromethane; at 20 ℃; for 72h;

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

Guidance literature:

With [Ru(DMF)nCl₂]2; hydrogen; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); 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:

ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

ethyl (2R,3S)-3-azido-2-benzoyloxy-3-phenylpropionate

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

(2S,3S)-3-Azido-2-hydroxy-3-phenyl ethyl propanoate

Downstream raw materials:

ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate