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

N-Benzoyl-(2R,3S)-3-phenylisoserine is a Taxol C-13 Side Chain and crucial for the strong antitumor activity of Taxol[1].

A mixture of N-benzoylphenylimine (0.30 mmol), rhodium acetate (0.006 mmol), silver hexafluorophosphate (0.03 mmol) molecular sieve (300 mg) was dissolved in 1.5 mL of LDCM (dichloromethane) solvent.The mixture solution A was prepared and stirred at 25 C for 5 minutes.Further, tert-butyl diazoacetate (0.33 mmol) was dissolved in 1.0 mL of LDCM (dichloromethane) solvent.Formulated as solution B. Solution B was added to the mixed solution A by a syringe pump at 25 C for 1 hour, and stirred for half an hour. Then, trifluoroacetic acid (0.90 mmol) was added to the obtained reaction.Continue to stir for hours. The reaction mixture is purified by flash column chromatography to give a pure product.Its structure is represented by the formula (1) and is N-benzoyl-(2R, 3S)-3-phenylisoserine.The yield was 85% and the dr value was equal to 92:8. A schematic of 1H NMR of the product is shown in Figure 23, and a 13C NMR scheme is shown in Figure 24.Synthesis of N-Benzoyl-(2R, 3S)-3-phenylisoseryl-CoA To a solution of

(2R,3S)-N-Benzoyl-3-phenylisoserine is an intermediate in the preparation of potent anticancer drug Paclitaxel (P132500) used to study the location of the binding sites. (2R,3S)-N-Benzoyl-3-phenylisoserine shows cytotoxic, antiviral andimmunomodulatory activity.

Molecular Weight:285.29
XLogP3:1.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:285.10010796
Monoisotopic Mass:285.10010796
Topological Polar Surface Area:86.6
Heavy Atom Count:21
Complexity:359
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes