Treatment of α,α′-dibromo-m-xylylene with 6-O-unprotected thiomaltoside 4 as glycosyl donor ( 5), followed by 4-O-unprotected galactoside derivative 6 as acceptor, afforded β-linked macrocyclic trisaccharide 9β in high yield after removal of the 3-O-MPM protective group and subsequent intramolecular glycoside bond formation. Similarly, by the same sequence of steps, the corresponding tetrasaccharide 14β was obtained from 5 and 4b-O-unprotected lactoside 11. For reiterative glycoside bond formation, treatment of α,α′-dibromo-m-xylylene with 3-O-unprotected thioglycoside 15 as donor ( 16), followed by 4,6-O-unprotected glucoside, and subsequent glycosylation afforded macrocyclic maltotrioside 22, which was transformed into known maltotrioside 23. A slight modification of the protecting-group pattern in maltotrioside synthesis resulted in generally higher yields in the ligation of the building blocks to the m-xylylene spacer, particularly in the second glycosylation step, thus providing macrocyclic maltotrioside 40α, which was transformed into known maltotriosides 41α and 41β.