TY - JOUR
T1 - Synthesis of Arabinoxylan Oligosaccharides by Pre-Activation-Based Iterative Glycosylations
AU - Underlin, Emilie Nørmølle
AU - Böhm, Maximilian Felix
AU - Madsen, Robert
PY - 2019
Y1 - 2019
N2 - A concise synthetic strategy has been developed for assembling densely substituted arabinoxylan oligosaccharides, which are valuable substrates for characterizing hemicellulose-degrading enzymes. The xylan backbone has been prepared by an iterative pre-activation-based glycosylation approach with phenyl thioglycosides. The pre-activation has been performed with in situ generated p-nitrobenzenesulfenyl triflate prior to addition of the acceptor. The glycosylation temperature was shown to have an important impact on the yield of the coupling. The arabinose substituents have been introduced in one high-yielding glycosylation with a N-phenyl trifluoroacetimidate donor. The strategy has been successfully employed for the synthesis of three heptasaccharides in seven steps and overall yields of 24 - 36% from the corresponding monosaccharide building blocks.
AB - A concise synthetic strategy has been developed for assembling densely substituted arabinoxylan oligosaccharides, which are valuable substrates for characterizing hemicellulose-degrading enzymes. The xylan backbone has been prepared by an iterative pre-activation-based glycosylation approach with phenyl thioglycosides. The pre-activation has been performed with in situ generated p-nitrobenzenesulfenyl triflate prior to addition of the acceptor. The glycosylation temperature was shown to have an important impact on the yield of the coupling. The arabinose substituents have been introduced in one high-yielding glycosylation with a N-phenyl trifluoroacetimidate donor. The strategy has been successfully employed for the synthesis of three heptasaccharides in seven steps and overall yields of 24 - 36% from the corresponding monosaccharide building blocks.
U2 - 10.1021/acs.joc.9b02529
DO - 10.1021/acs.joc.9b02529
M3 - Journal article
C2 - 31762276
SN - 0022-3263
VL - 84
SP - 16036
EP - 16054
JO - Journal of organic chemistry
JF - Journal of organic chemistry
IS - 24
ER -