TY - JOUR
T1 - Synthesis of ld-Hepp and KDO containing di- and tetrasaccharide derivatives of Neisseria meningitidis inner-core region via iodonium ion promoted glycosidations
AU - Boons, G. J.P.H.
AU - van Delft, F. L.
AU - van der Klein, P. A.M.
AU - van der Marel, G. A.
AU - van Boom, J. H.
PY - 1992/1/1
Y1 - 1992/1/1
N2 - The synthesis of methyl(ethyl) 2-thio-KDO i.e. 1, 2, 5, 7 and 10 and ethyl 1-thio-ldHepp (i.e. 26 and 43 derivatives will be described. The latter derivatives proved to be suitable donors in iodonium ion (NIS/TfOH) promoted glycosidation reactions. The usefulness of the glycosidation approach was illustrated by the successful conclusion of a spacer containing dimer l-α-d-Hepp(1→5)-α-KDO-2-O-(CH2)3NH2 (37) and tetramer β-d-Galp-(1→4)- β-dGlcp-(1→4)-l-α-d-Hepp(1→5)-α-KDO-2-O-(CH2)3NH2 (47).
AB - The synthesis of methyl(ethyl) 2-thio-KDO i.e. 1, 2, 5, 7 and 10 and ethyl 1-thio-ldHepp (i.e. 26 and 43 derivatives will be described. The latter derivatives proved to be suitable donors in iodonium ion (NIS/TfOH) promoted glycosidation reactions. The usefulness of the glycosidation approach was illustrated by the successful conclusion of a spacer containing dimer l-α-d-Hepp(1→5)-α-KDO-2-O-(CH2)3NH2 (37) and tetramer β-d-Galp-(1→4)- β-dGlcp-(1→4)-l-α-d-Hepp(1→5)-α-KDO-2-O-(CH2)3NH2 (47).
UR - http://www.scopus.com/inward/record.url?scp=0026584780&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)88191-6
DO - 10.1016/S0040-4020(01)88191-6
M3 - Article
AN - SCOPUS:0026584780
SN - 0040-4020
VL - 48
SP - 885
EP - 904
JO - Tetrahedron
JF - Tetrahedron
IS - 5
ER -