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
1995
Abstract
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)]
Details
Title
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
Author(s)
Zhu, Jieping ; Bouillon, Jean-Philippe ; Singh, Girij Pal
Published in
Tetrahedron Letters
Volume
36
Issue
39
Pages
7081-4
Date
1995
ISSN
0040-4039
Keywords
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)
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)
Laboratories
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25