Using glycals to form epoxide glycosyl donors 1,2-anhydrosugar glycosylation

3 Using glycals to form epoxide glycosyl donors 1,2-anhydrosugar glycosylation 

Synthesis of 6-0-(3,4,6-tri-(9-benzyl-(3-D-glucopyranosyl)-l,5-anhydro-3,4-di-(9-benzyl-2-deoxy-D-arabino-hex-l-enitol [76]. 

Notes and discussion. Note that this reaction has iterative potential—the product of the reaction can be subjected to further epoxidation conditions. The DMDO solution in acetone can be readily prepared using Oxone to oxidise acetone followed by distillation according to Murray s original method [58] and stored at — 20°C for periods of weeks. Note that large volumes of the DMDO solution are often required here 24 ml is used to produce just 45 mg of epoxide in the first stage. 

6-Tri-O-benzyl-D-glucal (43 mg, 0.10 mmol) 3,4-Di-O-benzyl-D-glucal (55.8 mg, 0.17 mmol) Dichloromethane, anhydrous (1 ml) 

Ethyl acetate and petroleum ether (bp 40-60 °C) for work-up and chromatography 

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