Androgene and anabolic agents by Vida J

By Vida J

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110 The addition of vinylic organometallic reagents to 69 gave a mixture of both D-gluco- and L-idofuranoses; more specifically, addition of vinylmagnesium bromide yielded an isomeric mixture of 79 and 80 in a ratio of 1:1. The L-idofuranose 80 was then converted into the IdoA derivative 83 via intermediate 81 by a sequence involving ozonolysis, oxidation, and methylation. In order to increase the diastereoselectivity of addition in favor of the L-ido isomer, the addition of different organometallic reagents to 69 was examined.

Forster, M. J. Conformation and Dynamics of Heparin and Heparan Sulfate. Glycobiology 2000, 10, 1147–1156. 11. ; Sasisekharan, R. Structural Insights into Biological Roles of Protein-Glycosaminoglycan Interactions. Chem. Biol. 2005, 12, 267–277. 12. ; Ferro, D. ; Jacquinet, J. ; Torri, G. Controversial Glycosaminoglycan Conformations. Nature 1986, 322, 215–216. 13. Ferro, D. ; Jacquinet, J. ; Choay, J. Evidence for Conformational Equilibrium of the Sulfated L-Iduronate Residue in Heparin and in Synthetic Heparin Mono- and Oligosaccharides—NMR and Force-Field Studies.

Eur. J. 2013, 19, 6817–6823. 53. van Boeckel, C. A. ; Vos, J. ; de Jong, A. J. ; Van Aelst, S. ; van den Bosch, R. ; Mertens, J. M. ; van der Vlugt, F. A. Synthesis of a Pentasaccharide Corresponding to the Antithrombin III Binding Fragment of Heparin. J. Carbohydr. Chem. 1985, 4, 293–321. 54. ; van Boeckel, C. A. ; Petitou, M. Biologically Active Heparin-Like Fragments with a “Non-Glycosamino” Glycan Structure. Part 1: A Pentasaccharide Containing a 3-O-Methyliduronic Acid Unit. Bioorg. Med. Chem.

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