An efficient short-step total synthesis of ganglioside GM3: effective usage of the neighbouring group participation strategy

Synthesis of oligosaccharide fragments corresponding to the exopolysaccharide released by Streptococcus macedonicus Sc 136

“…2) from suitably functionalized mono-and disaccharide intermediates are presented in Schemes 1, 2, 3, 4 and 5. Compounds 4-10 [18][19][20][21][22][23][24] were synthesized following earlier literature reports (Fig. 3).…”

“…The synthesis of compound 1 started with the glycosylation of the glycosyl acceptor 10 [24], prepared from D-glucose in three steps, with ethyl thioglycoside donor 4 [18], prepared from D-lactose octaacetate, in the presence of N-iodosuccinimide-methyltrifluoromethanesulfonate (NISTMSOTf) [25] to furnish trisaccharide derivative 11 in 78% yield. The compound 11 was converted to the trisaccharide derivative 12 in 60% over all yield following a sequence of reactions involving deacetylation, 3,4-Oisopropylidenation [26] and benzylation [27].…”

Benzenesulfenyl Chloride

“…71 Attempted addition of thiophenol to the 2-position of the ester-substituted indole failed, thus the addition/migration of PhSCl was used to install the desired moiety, with polyphosphoric acid cyclization giving the desired indole derivative (eq 38). 73 Thus, dehydration of a neuraminate afforded the corresponding glycal, which gave an anomeric chloride on addition of PhSCl. Furanoid glycals were employed as starting materials in the formation of nucleoside derivatives through the use of PhSCl.…”

Total Chemical Syntheses of the GM3 and F–GM3 Ganglioside Epitopes and Comparative Pre-Clinical Evaluation for Non-Invasive Imaging of Oligodendrocyte Differentiation

“…Previous syntheses of GM 3 favor a [2 + 1] coupling strategy in unifying a sialic acid component with a suitably protected lactose derivative (Figure ). − …”