The chemo-enzymatic synthesis is described of β-d-Glcp-(1->6)-[β-d-Galp-(1->4)]-β-d-GlcpNAc-(1->3)-β-d-Galp-(1->O(CH 2 ) 6 NH 2 (1), β-d-Glcp-(1->6)-[β-d-Galp-(1->4)]-β-d-GlcpNAc-(1->3)-β-d-Galp-(1->4)-β- d-Glcp-(1->O(CH 2 ) 6 NH 2 (2), β-d-Galp-(1->4)-β-d-GlcpNAc-(1->3)-β-d-Galp-(1->4)-β-d-Glcp-(1->O(CH 2 ) 6NH 2 (3), and β-d-Galp-(1->4)-β-d-GlcpNAc-(1->3)-β-d-Galp-(1->4)-β-d-Glcp-(1->6)-[β-d -Galp-(1->4)]-β-d-GlcpNAc-(1->O(CH 2 ) 6 NH 2 (4), representing fragments of the repeating unit of the Streptococcus pneumoniae serotype 14 capsular polysaccharide. Linear intermediate oligosaccharides 5-8 were synthesized via chemical synthesis, followed by enzymatic galactosylation using bovine milk β-1,4-galactosyltransferase as a catalyst. The title oligosaccharides form suitable compounds for conjugation with carrier proteins, to be tested as potential vaccines in animal models.