R. Verduyn, M. Douwes, P. A. M. Van Der Klein
1993
Citations
0
Influential Citations
50
Citations
Journal
Tetrahedron
Abstract
The ethylthio-laminaribioside 29, prepared by regiospecific glycosylation of ethyl 4,6-O-benzylidene-1-thio-β-d-glucopyranoside (9) with 2,3,4,6-tetra-O-benzoyl-d-glucopyranosyl imidate 17 and subsequent benzoylation, could be elongated in a step-wise fashion by consecutive iodonium ion promoted condensations with methyl 2,3,4-tri-O-benzoyl-α-d-glucopyranoside (5), ethyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-β-d-glucopyranoside (7), the laminaribioside 29 and ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-d-glucopyranoside (8), and intermittent protective group manipulations, to yield the partially acylated heptasaccharide 36. Finally, one-step deacylation of branched heptamer 36 afforded the target compound α-methyl 32,34-di-β-d-glucopyranosylgentiopentaoside (2).