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Application of the Dimethyl(phenyl)silyl Group as a Masked Form of the Hydroxy Group in the Synthesis of an L ‐ glycero ‐α‐ D ‐ manno ‐heptopyranoside‐Containing Trisaccharide from the Dephosphorylated Inner Core Region of Neisseria meningitidis
Author(s) -
Boons G. J. P. H.,
Overhand M.,
van der Marel G. A.,
van Boom J. H.
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198915041
Subject(s) - silylation , chemistry , oligosaccharide , cleavage (geology) , group (periodic table) , reagent , protecting group , stereochemistry , block (permutation group theory) , organic chemistry , catalysis , materials science , combinatorics , mathematics , alkyl , fracture (geology) , composite material
A favorable route to immunologically relevant oligosaccharides of type 1 makes use of the dimethyl(phenyl)silyl group (PhMe 2 Si). Addition of the Grignard reagent PhMe 2 SiCH 2 MgCl to a suitably protected D ‐mannodialdopyranose leads to chain lengthening at C‐6, i.e. formation of a heptopyranoside (Hepp) building block. The dimethyl(phenyl)silyl group functions thereby as equivalent of a protected hydroxy function. As precursor of 1 a completely protected triasaccharide was synthesized which additionally contained a spacer—for coupling with a polymeric support. Cleavage of the protecting groups affords the naturally occurring oligosaccharide 1 (with spacer).