Journal
CARBOHYDRATE RESEARCH
Volume 341, Issue 16, Pages 2714-2716Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2006.09.003
Keywords
1,2-anhydro-D-glucopyranose; 1,2-anhydro-D-galactopyranose; dimethyidioxirane; DMDO; epoxidation
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A multi-gram epoxidation of 3,4,6-tri-O-benzyl-D-glucal and D-galactal with dimethyldioxirane (DMDO) generated in situ from Oxone (R)/acetone in a biphasic system (CH2Cl2-aqueous NaHCO3) resulted in the formation of the corresponding 1,2-anhydrosugars in a 99% yield and 100% selectivity. In a similar way, 3,4,6-tri-O-acetyl-D-glucal afforded a 7:1 mixture of the corresponding gluco and manno derivatives in an 87% overall yield. (c) 2006 Elsevier Ltd. All rights reserved.
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