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Unexpected stereocontrolled access to 1α,1′β-disaccharides from methyl 1,2-ortho esters

AuthorsUriel, Clara ; Ventura, Juan ; Gómez, Ana M. ; López, J. Cristobal; Fraser-Reid, B.
Issue Date2015
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 77: 795-800 (2015)
AbstractMannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1α,1′β-disaccharides, upon treatment with BF 3•Et 2O in CH 2Cl 2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.
Identifiersdoi: 10.1021/jo202335n
issn: 0022-3263
e-issn: 1520-6904
Appears in Collections:(IQOG) Artículos
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