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A General and Diastereoselective Synthesis of 1,2-cis-Hexofuranosides from 1,2-trans-Thiofuranosyl Donors (2000)

Gelin, Muriel ; Ferrières, Vincent ; Plusquellec, Daniel

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 1423-1431

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ISSN: 1434-193X

Keywords: Carbohydrates ; Glycofuranosides ; Thiofuranosides ; Glycosylations ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: ---The general formation of 1,2-trans-thioglycofuranosides derived from D-galactose, D-glucose and D-mannose was readily accomplished starting from the corresponding alkyl glycofuranosides via per-O-acetyl-hexofuranoses as key synthons. Glycosidation of ethyl or phenyl perbenzylated 1,2-trans-thiofuranosides afforded disaccharides containing a nonreducing 1,2-cis-hexofuranosyl unit, i.e. α-D-galactosyl, α-D-glucosyl or β-D-mannosyl, with interesting diastereoselectivities. Activation of the thiofuranosyl donors was performed by N-iodosuccinimide and a catalytic amount of tin(II) trifluoromethanesulfonate.

Additional Material: 4 Tab.

Type of Medium: Electronic Resource

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