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

作者：Uriel Clara; Ventura Juan; Gomez Ana M; Cristobal Lopez J; Fraser Reid Bert

来源：European Journal of Organic Chemistry, 2012, 2012(16): 3122-3131.

DOI：10.1002/ejoc.201200089

• Carbohydrates
• Glycosylation
• Glycosyl donors
• Regioselectivity

Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and -benzoates (R = Ph) can function as glycosyl donors upon BF3 center dot Et2O activation in CH2Cl2 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 glycosylation protocols with monosaccharide diols, in which they display good regioselectivity.

• 出版日期2012-6