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
Résumé
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)]
Détails
Titre
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
Auteur(s)
Zhu, Jieping ; Bouillon, Jean-Philippe ; Singh, Girij Pal
Publié dans
Tetrahedron Letters
Volume
36
Numéro
39
Pages
7081-4
Date
1995
ISSN
0040-4039
Mots-clés (libres)
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)
Laboratoires
LSPN
Le document apparaît dans
Production scientifique et compétences > SB - Faculté des sciences de base > ISIC - Institut des sciences et ingénierie chimiques > LSPN - Laboratoire de synthèse et produits naturels
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Date de création de la notice
2010-11-25