Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 1, Pages 795-800Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo202335n
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Funding
- National Science Foundation [CHE 0717702]
- Ministerio de Ciencia e Innovation [CTQ2009-10343]
- Comunidad de Madrid [S2009/PPQ-1752]
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Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1 alpha,1'beta-disaccharides, upon treatment with BF3 center dot Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.
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