Asymmetric synthesis of 3,5-bis(isopropyloxy)-4-methoxyphenyl glycine by way of a diastereoselective Strecker reaction and an Evans electrophilic amination reaction
1998
Abstract
Two short syntheses of D-N-Boc-3,5-bis(isopropyloxy)-4-methoxyphenylglycine, a central unit of vancomycin type antibiotics, have been developed. A diastereoselective Strecker amination reaction using (S)-phenylglycinol as a chiral inducer was the key step in the first synthesis, while Evans' electrophilic azidation technol. was employed for introducing both the amino function and the chirality in the second strategy. [on SciFinder (R)]
Details
Title
Asymmetric synthesis of 3,5-bis(isopropyloxy)-4-methoxyphenyl glycine by way of a diastereoselective Strecker reaction and an Evans electrophilic amination reaction
Author(s)
Vergne, Caroline ; Bouillon, Jean-Philippe ; Chastanet, Jacqueline ; Bois-Choussy, Michele ; Zhu, Jieping
Published in
Tetrahedron: Asymmetry
Volume
9
Issue
17
Pages
3095-3103
Date
1998
ISSN
0957-4166
Keywords
Amination (Strecker; diastereoselective; asym. synthesis of bis(isopropyloxy)methoxyphenylglycine using two different strategies); Asymmetric synthesis and induction (asym. synthesis of bis(isopropyloxy)methoxyphenylglycine using two different strategies); Substitution reaction (azidation; Evans' electrophilic; asym. synthesis of bis(isopropyloxy)methoxyphenylglycine using two different strategies); glycine bisisopropyloxymethoxyphenyl asym synthesis; amination diastereoselective Strecker phenylglycinol chiral reagent; azidation electrophilic Evans one step chirality amino group addn
Note
CAN 130:52700
34-2
Amino Acids, Peptides, and Proteins
Institute de Chimie des Substances Naturelles, CNRS,Gif-Sur-Yvette,Fr.
Journal
written in English.
2627-86-3 ((S)-alpha -Methylbenzylamine); 20989-17-7 ((S)-Phenylglycinol); 128677-61-2; 171738-30-0; 171738-31-1 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. synthesis of bis(isopropyloxy)methoxyphenylglycine using two different strategies); 171738-32-2P; 171738-33-3P; 171738-34-4P; 171738-35-5P; 178744-35-9P; 178744-36-0P; 178744-37-1P; 178744-38-2P; 217494-26-3P; 217494-28-5P; 217494-29-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. synthesis of bis(isopropyloxy)methoxyphenylglycine using two different strategies); 217494-25-2P; 217494-27-4P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of bis(isopropyloxy)methoxyphenylglycine using two different strategies); 1404-90-6 (Vancomycin) Role: MSC (Miscellaneous) (asym. synthesis of bis(isopropyloxy)methoxyphenylglycine, central unit of vancomycin)
34-2
Amino Acids, Peptides, and Proteins
Institute de Chimie des Substances Naturelles, CNRS,Gif-Sur-Yvette,Fr.
Journal
written in English.
2627-86-3 ((S)-alpha -Methylbenzylamine); 20989-17-7 ((S)-Phenylglycinol); 128677-61-2; 171738-30-0; 171738-31-1 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. synthesis of bis(isopropyloxy)methoxyphenylglycine using two different strategies); 171738-32-2P; 171738-33-3P; 171738-34-4P; 171738-35-5P; 178744-35-9P; 178744-36-0P; 178744-37-1P; 178744-38-2P; 217494-26-3P; 217494-28-5P; 217494-29-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. synthesis of bis(isopropyloxy)methoxyphenylglycine using two different strategies); 217494-25-2P; 217494-27-4P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of bis(isopropyloxy)methoxyphenylglycine using two different strategies); 1404-90-6 (Vancomycin) Role: MSC (Miscellaneous) (asym. synthesis of bis(isopropyloxy)methoxyphenylglycine, central unit 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