A high-yielding synthesis of allyl glycosides from peracetylated glycosyl donors.
β-Configured peracetylated sugars are often used as easily accessible glycosyl donors that are typically activated with common Lewis acids such as boron trifluoride or trimethylsilyltrifluoromethane sulfonate. Often these glycosylations occur with unsatisfactory yields due to incomplete reactions or extensive byproduct formation, primarily as a result of loss of an additional acetyl group generating partially unprotected glycosides. Here we report a simple glycosylation-reacetylation protocol for the generation of predominantly β-configured peracetylated allyl glucoside, -galactoside, -lactoside, and -maltoside with substantially improved reaction yields.
Department of Chemistry, University of Texas at El Paso, 500 West University Avenue, El Paso, TX 79968, USA.
Jamal
J
Khamsi
Roger A
RA
Ashmus
Nathaniel S
NS
Schocker
Katja
K
Michael
D000085:Acetates / Q000737:chemistry*; D000107:Acetylation; D002236:Carbohydrate Conformation; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D058116:Lewis Acids / Q000737:chemistry
D000085:Acetates; D006027:Glycosides; D058116:Lewis Acids