Methyl 1, 2??Orthoesters as Useful Glycosyl Donors in Glycosylation Reactions: A Comparison with n??Pent??4??enyl 1, 2??Orthoesters

…, AM Gómez, JC López, B Fraser??Reid

Index: Uriel, Clara; Ventura, Juan; Gomez, Ana M.; Lopez, J. Cristobal; Fraser-Reid, Bert Journal of Organic Chemistry, 2012 , vol. 77, # 1 p. 795 - 800

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Abstract

Abstract Mannopyranose-derived methyl 1, 2-orthoacetates (R= Me) and-benzoates (R= Ph) can function as glycosyl donors–upon BF 3· Et 2 O activation in CH 2 Cl 2–in glycosylation reactions with monosaccharide acceptors to afford disaccharides in good yields. In the process, glycosylation is preferred to acid-catalyzed rearrangement leading to methyl mannopyranosides. Methyl 1, 2-orthoesters can be also used in regioselective ...

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