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Wiley, European Journal of Organic Chemistry, 8(2000), p. 1423-1431, 2000

DOI: 10.1002/(sici)1099-0690(200004)2000:8<1423::aid-ejoc1423>3.0.co;2-9

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A General and Diastereoselective Synthesis of 1,2‐cis‐Hexofuranosides from 1,2‐trans‐Thiofuranosyl Donors

Journal article published in 2000 by Muriel Gelin, Vincent Ferrières ORCID, Daniel Plusquellec
This paper is available in a repository.
This paper is available in a repository.

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Abstract

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.