(2R,3S)-3-PHENYLISOSERINE ETHYLESTER

Base Information

• Chemical Name: (2R,3S)-3-PHENYLISOSERINE ETHYLESTER
• CAS No.: 153433-80-8
• Molecular Formula: C18H19 N O4
• Molecular Weight: 313.353
• Mol file: 153433-80-8.mol

Synonyms:Benzenepropanoicacid, b-(benzoylamino)-a-hydroxy-, ethyl ester,[R-(R*,S*)]-; Ethyl (2R,3S)-3-(benzoylamino)-2-hydroxybenzenepropanoate

Chemical Property of (2R,3S)-3-PHENYLISOSERINE ETHYLESTER

Chemical Property:

• Melting Point: 162～163℃
• Boiling Point: 546.8±50.0 °C(Predicted)
• PKA: 12.19±0.20(Predicted)
• PSA: 72.55000
• Density: 1.211±0.06 g/cm3(Predicted)
• LogP: 1.31070
• Solubility.: Chloroform, Ethyl Acetate, Methanol

Purity/Quality:

99% ^*data from raw suppliers

(2R,3S)-N-Benzoyl-3-phenylIsoserineEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2R,3S)-3-PHENYLISOSERINE ETHYLESTER is an intermediate in the preparation of potent anticancer drug Paclitaxel (P132500) used to study the location of the binding sites. (2R,3S)-3-PHENYLISOSERINE ETHYLESTER shows cytotoxic, antiviral and immunomodulatory activity.

Technology Process of (2R,3S)-3-PHENYLISOSERINE ETHYLESTER

There total 51 articles about (2R,3S)-3-PHENYLISOSERINE ETHYLESTER 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: 98.0%

ethyl (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate (869012-73-7) → ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (153433-80-8)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 1.5h;

DOI:10.1016/j.tetasy.2005.08.015

Reference yield: 90.0%

diazoacetic acid ethyl ester (623-73-4) + N-benzylidenebenzamide (10374-29-5) → ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (153433-80-8)

Guidance literature:

N-benzylidenebenzamide; With dirhodium tetraacetate; silver(I) hexafluorophosphate; In dichloromethane; at 25 ℃; for 0.0833333h; Molecular sieve;

diazoacetic acid ethyl ester; In dichloromethane; at 25 ℃; for 1.5h;

With trifluoroacetic acid; In dichloromethane; for 1h;

Reference yield: 90.0%

ethyl (2R,3S)-3-azido-2-O-benzoyl-3-phenylpropionate (246861-68-7) → ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (153433-80-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 6h; under 2585.74 Torr;

upstream raw materials:

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

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

ethyl (2R,3S)-3-azido-2-O-benzoyl-3-phenylpropionate

ethyl (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate

Downstream raw materials:

(2R,3S)-N-benzoyl-3-phenylisoserine

(4S-trans)-3-benzoyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid ethyl ester

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

Refernces

• 1、 -. "N-benzoyl phenylisoserine derivative as well as synthesis method and application thereof". Paragraph 0072-0075. . Retrieved 2019/09/14.
• 2、 Rimoldi, Isabella,Pellizzoni, Michela,Facchetti, Giorgio,Molinari, Francesco,Zerla, Daniele,Gandolfi, Raffaella. "Chemo- and biocatalytic strategies to obtain phenylisoserine, a lateral chain of Taxol by asymmetric reduction". experimental part. p. 2110 - 2116. Retrieved 2012/03/27.