Addition of Organozinc Reagents to Glycopyranosyl Cyanides: Access to Keto Ester‐C‐glycosides or Unsaturated Acyl‐C‐glycosides

Addition of Organozinc Reagents to Glycopyranosyl Cyanides: Access to Keto Ester‐C‐glycosides or Unsaturated Acyl‐C‐glycosides

Addition of Reformatsky‐type or allylic zinc reagents to 2,3,4,6‐tetra‐O‐benzylglycopyranosyl cyanides led to keto ester‐C‐glycosides or unsaturated acyl‐C‐glycosides in moderate to excellent yields in the galactose, glucose, and mannose series. Original keto ester‐C‐glycosides or unsaturated acyl‐C...

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Veröffentlicht in:European journal of organic chemistry 2018-04, Vol.2018 (14), p.1735-1738
Hauptverfasser: Ella Obame, Idriss, Ireddy, Prathap, Guisot, Nicolas E. S., Nourry, Arnaud, Saluzzo, Christine, Dujardin, Gilles, Dubreuil, Didier, Pipelier, Muriel, Guillarme, Stéphane
Format: Artikel
Sprache:eng
Schlagworte:
Addition reactions
Carbohydrates
Chemical Sciences
Cyanides
C‐glycosides
Galactose
Keto esters
Mannose
Organic chemistry
Organozinc reagents
Reagents
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Zusammenfassung:Addition of Reformatsky‐type or allylic zinc reagents to 2,3,4,6‐tetra‐O‐benzylglycopyranosyl cyanides led to keto ester‐C‐glycosides or unsaturated acyl‐C‐glycosides in moderate to excellent yields in the galactose, glucose, and mannose series. Original keto ester‐C‐glycosides or unsaturated acyl‐C‐glycosides have been prepared in moderate to excellent yields in the galactose, glucose and mannose series by reactions involving addition of Reformatsky‐type or allylic zinc reagents to 2,3,4,6‐tetra‐O‐benzylglycopyranosyl cyanides.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201800090