Diastereoselective synthesis of furanose and pyranose substituted glycine and alanine derivatives via proline-catalyzed asymmetric α-amination of aldehydes.
Carbohydr Res
; 435: 37-49, 2016 Nov 29.
Article
em En
| MEDLINE
| ID: mdl-27693912
ABSTRACT
A concise organocatalytic route toward the synthesis of furanose and pyranose substituted glycine and alanine derivatives is reported. These compounds are core structural units of some of the naturally available antibiotics and antifungal agents. Proline-catalyzed asymmetric α-amination of aldehydes derived from sugars is used as the key reaction to synthesize twelve sugar amino acid derivatives. The asymmetric transformations proceeded in good yields and with good to excellent diastereoselectivity. The application of the synthesized amino acids is demonstrated by synthesizing a tripeptide containing one of them.
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Base de dados:
MEDLINE
Assunto principal:
Alanina
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Aldeídos
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Amino Açúcares
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Glicina
Idioma:
En
Ano de publicação:
2016
Tipo de documento:
Article