O-(3-Butenyl), a stable blocking group removable by ozonolysis

Article abstract of DOI:10.1016/0008-6215(92)80070-H

Among the many blocking groups used in carbohydrate chemistry, only a few can be removed under very mild and neutral conditions, while resisting the reagents generally applied in chemical reactions. We demonstrate here the utility of the O-(3-butenyl) group for differential protection in carbohydrates. The 3-butenyl group is readily attached to the anomeric oxygen atom of any reducing mono- or oligo-saccharide, using either the Koenigs-Knorr or Fischer type of reaction with 3-buten-1-ol as the aglyconic alcohol.