Journal
JOURNAL OF CARBOHYDRATE CHEMISTRY
Volume 32, Issue 5-6, Pages 380-391Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/07328303.2013.809093
Keywords
Immobilized sulfuric acid; Silica gel; 3,4,6-Tri-O-benzyl-d-glucal; Glycosylation; Ferrier rearrangement
Funding
- National Students Innovative Experimental Projects [091026911]
- Natural Science Foundation of Shanghai [11ZR1410400]
- large instruments Open Foundation of East China Normal University [2011-76, 2012-9]
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Sulfuric acid immobilized on silica gel (H2SO4-SiO2) was used as an efficient and convenient promoter for Ferrier-type rearrangement of 3,4,6-tri-O-benzyl-d-glucal in CH2Cl2, which is a difficult donor for this type of reaction. The acceptors include primary alcohols, secondary alcohols, pentanol, halogenated alcohol, sterols, thiol, and 2-naphthol. Thus, 2,3-unsaturated glycosides were obtained rapidly (<2h) and efficiently (>62%) in good -selectivity (/>4.2:1) under mild conditions.
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