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Wiley-VCH Verlag, ChemInform, 12(34), 2003

DOI: 10.1002/chin.200312182

Elsevier, Bioorganic and Medicinal Chemistry Letters, 24(12), p. 3515-3518

DOI: 10.1016/s0960-894x(02)00822-3

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A Novel Synthesis of D-Galactofuranosyl, D-Glucofuranosyl and D-Mannofuranosyl 1-Phosphates Based on Remote Activation of New and Free Hexofuranosyl Donors.

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Abstract

The selective synthesis of 1,2-cis-hexofuranosyl 1-phosphates was readily accomplished according to a procedure based on the 'Remote Activation Concept'. This approach required (i) the preparation of suitable 1,2-trans-hexofuranosyl donors, so that new heterocyclic thiofuranosides were designed and synthesized, (ii) the stereocontrolled phosphorylation of the corresponding unprotected donors and (iii) the simple and fast purification of the resulting anomeric phosphates. This approach showed to be equally efficient in the galactose, glucose and mannose series.