AbstractWe have developed a versatile deprotection method for the synthesis of 2‐deoxyoligosaccharides containing a 1,4‐dialkylhydroquinone moiety at the anomeric position. The Birch reduction of a 2,6‐dideoxy monosaccharide with potassium and 1,3‐pentadiene gave the deprotected product without any undesired reduction. The utility of this method was then demonstrated in the Birch reduction of a landomycin E deoxytrisaccharide. Pd‐catalysed hydrogenation led to the anomerization, or cleavage, of the glycosidic linkages. In contrast, Birch reduction based on the optimized conditions followed by treatment with mCPBA (m‐chloroperoxybenzoic acid) provided the fully deprotected deoxytrisaccharide in 65 % overall yield. These results show that the Birch reduction is a powerful deprotection method for the synthesis of complex natural glycosides, including 2‐deoxyoligosaccharides.