S-Benzoxazolyl (SBox) Glycosides in Oligosaccharide Synthesis: Novel Glycosylation Approach to the Synthesis of β-d-Glucosides, β-d-Galactosides, and α-d-Mannosides

Alexei V. Demchenko; Medha N. Kamat; Cristina De Meo

doi:10.1055/s-2003-40345

LETTER

S-Benzoxazolyl (SBox) Glycosides in Oligosaccharide Synthesis: Novel Glycosylation Approach to the Synthesis of β-d-Glucosides, β-d-Galactosides, and α-d-Mannosides

Alexei V. Demchenko*, Medha N. Kamat, Cristina De Meo
Department of Chemistry and Biochemistry, University of Missouri - St. Louis, 8001 Natural Bridge Rd., St. Louis, MO 63121, USA
Fax: +1(314)5165342; e-Mail: demchenkoa@umsl.edu;

Abstract

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Abstract

Per-acetylated and per-benzoylated S-benzoxazolyl (SBox) glycosides have been synthesized and applied to highly efficient 1,2-trans glycosylation. Complete stereoselectivities and remarkably high yields were achieved for the synthesis of β-d-glucosides, β-d-galactosides, and α-d-mannosides. It was also demonstrated that benzoylated ‘disarmed’ SBox glycosides could be selectively activated in the presence of both armed and disarmed ethyl thioglycosides. Convergent synthesis of the tetrasaccharide β-d-Glc-(1-6)-β-d-Gal-(1-6)-β-d-GlcNAc-(1-6)-α-d-GlcOMe was achieved in three sequential selective glycosylation steps.

Key words

carbohydrates - stereoselective synthesis - glycosylation - chemoselectivity

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References

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