TMS Triflate-Promoted O-Glycosylation of Amino Acids and Peptides by L-Acosaminal and L-Ristosaminal

TMS Triflate-Promoted O-Glycosylation of Amino Acids and Peptides by L-Acosaminal and L-Ristosaminal

Cyclic and linear peptides are stereoselectively O‐glycosylated by 3‐(acylamino)glycals through activation with TMS triflate (trimethylsilyl trifluoromethanesulfonate) without Ferrier rearrangement. The yields of the 2‐deoxy‐α‐O‐glycosides obtained range from 18 to 95%.

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Veröffentlicht in:Liebigs Annalen der Chemie 1994-08, Vol.1994 (8), p.811-816
Hauptverfasser: Kessler, Horst, Michael, Katja, Kottenhahn, Matthias
Format: Artikel
Sprache:eng
Schlagworte:
Amino acids
Carbohydrates
Chemistry
Exact sciences and technology
Glycopeptides
Glycosides
Glycosylations
Organic chemistry
Peptides
Preparations and properties
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Beschreibung
Zusammenfassung:Cyclic and linear peptides are stereoselectively O‐glycosylated by 3‐(acylamino)glycals through activation with TMS triflate (trimethylsilyl trifluoromethanesulfonate) without Ferrier rearrangement. The yields of the 2‐deoxy‐α‐O‐glycosides obtained range from 18 to 95%.
ISSN:0170-2041
1099-0690
DOI:10.1002/jlac.199419940809