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Elsevier, Tetrahedron Letters, 49(53), p. 6633-6636

DOI: 10.1016/j.tetlet.2012.08.127

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Selective derivatization of d-galactose towards a practical synthesis of C-6 l-fucose analogues

Journal article published in 2012 by Rui C. Pinto, Marta M. Andrade, Maria Teresa Barros ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

Starting from d-galactose, a convenient protocol is described for the synthesis of l-fucose C-6 analogue, 2,3,4,5-tetra-O-acetyl-5-(1,3-dithiolan-2-yl)-l-galactopyranose, in an overall yield of 40% after 6 steps, making use of stable intermediates. A chemoselective protection/deprotection strategy was studied using TBDMS and TBDPS silyl ethers for protection of d-galactose primary hydroxyl group.