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Digitale Medien

Activation of Glycosyl Phosphites under Neutral Conditions in Solutions of Metal Perchlorates in Organic Solvents (1998)

Schene, Heidrun ; Waldmann, Herbert

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 1227-1230

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Details

ISSN: 1434-193X

Schlagwort(e): Glycosides ; Glycosylations ; Glycosyl phosphites ; Metal perchlorates ; LiClO4-solvent mixtures ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Glycosyl phosphites 1-3 derived from glucose are activated under neutral conditions and without the addition of any further promoter in 1 M solutions of LiClO4, Mg(ClO4)2 or Ba(ClO4)2 in ether, CH2Cl2, or CH3CN and react under these conditions with the alcohols5-9 to give the glycosides 10-14. The best results are obtained in the presence of Ba(ClO4)2. In CH2Cl2 and ether the α-anomers predominate, in CH3CN the β-isomers are formed in excess. Whereas the methyl phosphite 1 and the benzyl phosphite 3 deliver the desired glycosides in yields of 35-66%, the ethyl phosphite 2 is a more reactive glycosyl donor, giving the glycosides 10, 11 and 13 in 62-95% yield.

Materialart: Digitale Medien

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