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A Ramberg-Backlund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids

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JournalEuropean Journal of Organic Chemistry
DatePublished - Apr 2002
Issue number7
Number of pages14
Pages (from-to)1323-1336
Original languageEnglish

Abstract

Synthetic applications of exo-glycals, derived from S-glycoside dioxides using the Meyers variant of the Ramberg-Backlund rearrangement, are described. These include a formal synthesis of a beta-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg-Backlund rearrangement is also reported. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

    Research areas

  • carbohydrates, sulfones, rearrangements, exo-glycals, STEREOSELECTIVE SYNTHESIS, OLEFIN METATHESIS, EXO-GLYCALS, PREFERRED CONFORMATION, L-SERINE, ANALOG, CONVERGENT, INHIBITORS, SUGARS, ROUTE

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