Stereoselective synthesis of a ketohexofuranose from an aldohexopyranose by a [6+1-1] strategy.
Carbohydr Res
; 340(4): 753-8, 2005 Mar 21.
Article
em En
| MEDLINE
| ID: mdl-15721349
ABSTRACT
Ozonolysis of 2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hex-1-enitol gave 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose (5). Subsequent hydrolysis and acetylation of 5 provided 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D-fructofuranose 6 in excellent yield. This methodology allows specific deuteration at C-1 of a protected D-fructofuranose derivative. This approach therefore could serve as [6+1-1] formulation for hexose series inter-conversion, that is, aldohexopyranose to ketohexofuranose.
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01-internacional
Base de dados:
MEDLINE
Assunto principal:
Arabinose
Idioma:
En
Revista:
Carbohydr Res
Ano de publicação:
2005
Tipo de documento:
Article
País de afiliação:
Índia