Asymmetric synthesis of (2S,3R) beta -(4-F-3-NO2) phenyl serine, D-(R)-4-methoxy-3,5-bistbutyldimethylsiloxy phenylglycine and their assemblage to C-O-D ring of vancomycin

The asym. synthesis of two appropriately functionalized nonproteinogenic amino acids I (Troc = CO2CH2CCl3, TBS = SiMe2CMe3) and II (Boc = Me3CO2C) needed for the total synthesis of vancomycin is described. The assemblage of these amino acids into linear tripeptide followed by biaryl ether formation via intramol. SNAr reaction led to the fully functionalized C-O-D ring III of vancomycin. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 36, 39, 7081-4
Year:
1995
Keywords:
Note:
CAN 124:30381
34-3
Amino Acids, Peptides, and Proteins
Inst. Chim. Subst. Nat.,CNRS,Gif-sur-Yvette,Fr.
Journal
0040-4039
written in English.
1404-90-6P (Vancomycin) Role: PNU (Preparation, unclassified), PREP (Preparation) (asym. synthesis of protected [fluoro(nitro)phenyl]serine and protected [methoxy(dihydroxy)phenyl]glycine and their assemblage to C-O-D ring of vancomycin); 99-24-1 (Methyl gallate); 875-74-1 (D-Phenylglycine); 20989-17-7 ((S)-Phenylglycinol); 42564-51-2 (4-Fluoro-3-nitrobenzaldehyde); 104324-16-5 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. synthesis of protected [fluoro(nitro)phenyl]serine and protected [methoxy(dihydroxy)phenyl]glycine and their assemblage to C-O-D ring of vancomycin); 13089-97-9P; 20189-90-6P; 104324-17-6P; 104324-18-7P; 171738-27-5P; 171738-28-6P; 171738-30-0P; 171738-31-1P; 171738-32-2P; 171738-33-3P; 171738-34-4P; 171738-35-5P; 171738-36-6P; 171738-37-7P; 171738-38-8P; 171738-39-9P; 171738-40-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. synthesis of protected [fluoro(nitro)phenyl]serine and protected [methoxy(dihydroxy)phenyl]glycine and their assemblage to C-O-D ring of vancomycin); 171738-29-7P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of protected [fluoro(nitro)phenyl]serine and protected [methoxy(dihydroxy)phenyl]glycine and their assemblage to C-O-D ring of vancomycin)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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