research article

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

Zhu, Jieping  
•
Bouillon, Jean-Philippe
•
Singh, Girij Pal
1995
Tetrahedron Letters

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)]

Type
research article
DOI
10.1016/0040-4039(95)01409-B
Author(s)
Zhu, Jieping  
•
Bouillon, Jean-Philippe
•
Singh, Girij Pal
Date Issued

1995

Publisher

Elsevier

Published in
Tetrahedron Letters
Volume

36

Issue

39

Start page

7081

End page

4

Subjects

Asymmetric synthesis and induction (asym. synthesis of protected [fluoro(nitro)phenyl]serine and protected [methoxy(dihydroxy)phenyl]glycine and their assemblage to C-O-D ring of vancomycin)

•

vancomycin ring fragment asym synthesis; phenylserine protected fluoronitro asym synthesis; fluoronitrophenylserine protected asym synthesis; methoxydihydroxyphenylglycine protected asym synthesis; phenylglycine protected methoxydihydroxy asym synthesis

Note

CAN 124:30381

34-3

Amino Acids, Peptides, and Proteins

Inst. Chim. Subst. Nat.,CNRS,Gif-sur-Yvette,Fr.

Journal

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)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58565