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Synthesis 1995; 1995(4): 409-414
DOI: 10.1055/s-1995-3918
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Stannylene Activation in Glycoside Synthesis: Regioselective Glycosidations at the Primary Position of Galactopyranosides Unprotected in the 2-, 3-, 4-, and 6-Positions

Per J. Garegg* , Jean-Luc Maloisel, Stefan Oscarson
  • *Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-10691 Stockholm, Sweden
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Publication Date:
31 December 2000 (online)

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Stannylene activation with dibutyltin oxide of methyl D-galactopyranosides and of methyl β-D-glucopyranoside, respectively, followed by glycosidation with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide promoted by tetrabutylammonium iodide, or followed by glycosidation with ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside, or ethyl 2,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside, or ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside, the latter four glycosyl donors being promoted by dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST), led to regioselective glycosidation at the 6-OH of the stannylene glycosyl acceptors. This selectivity was not observed in the absence of stannylene activation.

oligosaccharides - dibutyltin activation - selective glycosidation