Synthesis of Saponins Using Partially Protected Glycosyl Donors

[reaction: see text] A new class of glycosyl donors having unprotected 2- and 2,4-hydroxyl groups were investigated under the standard glycosylation conditions. This approach was shown to be generally effective for the synthesis of alkyl and steroidal glycosides. A natural saponin, containing 2,4-branched oligosaccharide, was prepared in 35% overall yield in four straightforward sequential reactions by taking advantage of these partially protected donors.