Asymmetric synthesis of 3,5-bis(isopropyloxy)-4-methoxyphenyl glycine by way of a diastereoselective Strecker reaction and an Evans electrophilic amination reaction
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)]
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Vergne, C., Bouillon, J.-P., Chastanet, J., Bois-Choussy, M., & Zhu, J. (1998). Asymmetric synthesis of 3,5-bis(isopropyloxy)-4-methoxyphenyl glycine by way of a diastereoselective Strecker reaction and an Evans electrophilic amination reaction. Tetrahedron: Asymmetry, 9(17), 3095–3103. https://doi.org/10.1016/S0957-4166(98)00312-7
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1998
9
17
3095
3103
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)
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