The total synthesis of C-glycosides with completely resolved seven-carbon backbone polyol stereochemistry: stereochemical correlations and access to L-configured and other rare carbohydrates.
Chemistry
; 7(22): 4771-89, 2001 Nov 19.
Article
em En
| MEDLINE
| ID: mdl-11763446
ABSTRACT
The de novo synthesis of a full set of hydroxymethyl C-glycosides from only two precursors is described. The seven-carbon target molecules contain five stereocentres and bridge the stereochemical gap between natural D-configured and non-natural L-configured series of hexoses. Key steps include hydroxylation, differential protection, stereoselective reduction and desymmetrization of 8-oxabicyclo[3.2.1]oct-6-enes. C-Terminus differentiation and C-terminus excision of the seven-carbon polyol backbone lead to hexoses, including those of the L-series. A stereochemical and genetic classification of C-glycosides is presented.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Glicosídeos
Idioma:
En
Revista:
Chemistry
Assunto da revista:
QUIMICA
Ano de publicação:
2001
Tipo de documento:
Article
País de afiliação:
Alemanha