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J Org Chem. 2009 Mar 6;74(5):1994-2003. doi: 10.1021/jo8025274.

Facile synthesis of per-O-tert-butyldimethylsilyl-beta-D-galactofuranose and efficient glycosylation via the galactofuranosyl iodide.

Author information

  • 1CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina.

Abstract

The synthesis of crystalline per-O-TBS-beta-D-galactofuranose (4beta) as a new precursor of D-Gal f units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new efficient glycosylation method for the assembly of D-galactofuranosyl moieties with high beta-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved.

PMID:
19215102
[PubMed - indexed for MEDLINE]
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