TY - JOUR
T1 - A novel glycosylation of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via in situ pyranose-furanose rearrangement
AU - Sun, Xue
AU - Kai, Toshitsugu
AU - Fujita, Syuji
AU - Takayanagi, Hiroaki
AU - Furuhata, Kimio
PY - 1997/1/1
Y1 - 1997/1/1
N2 - In studies on the glycosylation of 3-deoxy-D-glycero-D-galacto-2- nonulosonic acid (KDN) derivatives, O-glycosides of furanose-type KDN were synthesized from benzyl 4,5,7,8,9-penta-O-acetyl-2-bromo-2,3-dideoxy-D- glycero-D-galacto-2-nonulopyranosonate under Koenigs-Knorr reaction conditions. The furanoid structures of the KDN moiety were supported by with 1H-NMR experiments, and the reaction was considered as a novel glycosylation with ring contraction, which proceeded via in situ pyranose-furanose rearrangement of the KDN moiety, and subsequent coupling with acceptors.
AB - In studies on the glycosylation of 3-deoxy-D-glycero-D-galacto-2- nonulosonic acid (KDN) derivatives, O-glycosides of furanose-type KDN were synthesized from benzyl 4,5,7,8,9-penta-O-acetyl-2-bromo-2,3-dideoxy-D- glycero-D-galacto-2-nonulopyranosonate under Koenigs-Knorr reaction conditions. The furanoid structures of the KDN moiety were supported by with 1H-NMR experiments, and the reaction was considered as a novel glycosylation with ring contraction, which proceeded via in situ pyranose-furanose rearrangement of the KDN moiety, and subsequent coupling with acceptors.
KW - 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid
KW - Glycosylation
KW - KDN
KW - Koenigs-Knorr reaction
KW - Pyranose-furanose rearrangement
UR - https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0030966583&origin=inward
UR - https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=0030966583&origin=inward
U2 - 10.1248/cpb.45.795
DO - 10.1248/cpb.45.795
M3 - Article
SN - 0009-2363
VL - 45
SP - 795
EP - 798
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 5
ER -