Synthesis, Table of Contents Synthesis 2019; 51(12): 2484-2488DOI: 10.1055/s-0037-1611800 psp © Georg Thieme Verlag Stuttgart · New YorkPractical Gram-Scale Synthesis of Either α- or β-Anomer of C-Vinyl Glycosides Authors Author Affiliations Florian Rouzier a IMMM - UMR 6283 CNRS, Le Mans Université, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France Email: stephane.guillarme@univ-lemans.fr Rosanne Sillé a IMMM - UMR 6283 CNRS, Le Mans Université, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France Email: stephane.guillarme@univ-lemans.fr Arnaud Nourry a IMMM - UMR 6283 CNRS, Le Mans Université, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France Email: stephane.guillarme@univ-lemans.fr Arnaud Tessier b CEISAM, UMR 6220 CNRS, Université de Nantes, Faculté des Sciences et des Techniques, 2, rue de la Houssinière, 44322 Nantes cedex 3, France Muriel Pipelier b CEISAM, UMR 6220 CNRS, Université de Nantes, Faculté des Sciences et des Techniques, 2, rue de la Houssinière, 44322 Nantes cedex 3, France Stéphane Guillarme* a IMMM - UMR 6283 CNRS, Le Mans Université, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France Email: stephane.guillarme@univ-lemans.fr Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract The synthesis C-vinyl glycosides, useful intermediates for the synthesis of C-glycoconjugates, was carried out on gram-scale by controlled reduction of the corresponding ethynyl derivatives in good to excellent yields in different carbohydrate series. Key words Key words C-glycosides - controlled reduction - alkynes - gram-scale Full Text References References 1 Yang G, Schmieg J, Tsuji M, Franck RW. Angew. Chem. Int. Ed. 2004; 43: 3818 For example, see: 2a Chen G, Schmieg J, Tsuji M, Franck RW. Org. Lett. 2004; 6: 4077 2b Kulkarni SS, Gervay-Hague J. Org. Lett. 2006; 8: 5765 2c Dondoni A, Giovannini PP, Marra A. J. Chem. Soc., Perkin Trans. 1 2001; 2380 3a Zhdanov YuA, Korol’chenko GA, Kubasskaya LA, Krivoruchko RM. Dokl. Akad. Nauk. SSSR. 1959; 129: 1049 3b Shul’man ML, Shiyan SD, Khorlin AYa. Carbohydr. Res. 1974; 33: 229 3c Werschkun B, Thiem J. Angew. Chem. Int. Ed. 1998; 36: 2793 3d Juers S, Thiem J. Tetrahedron: Asymmetry 2005; 16: 1631 3e Jürs S, Werschkun B, Thiem J. Eur. J. Org. Chem. 2006; 4451 3f Lin YA, Chalker JM, Davis BG. J. Am. Chem. Soc. 2010; 132: 16805 4a Kraus GA, Molina MT. J. Org. Chem. 1988; 53: 752 4b Xie J, Durrat F, Valery J.-M. J. Org. Chem. 2003; 68: 7896 4c Kang SY, Song K.-S, Lee J, Lee S.-H, Lee J. Bioorg. Med. Chem. 2010; 18: 6069 Benzyl protection: 5a Rainier J, Cox J. Org. Lett. 2000; 2: 2707 5b Chang R, Vo T.-T, Finney NS. Carbohydr. Res. 2006; 341: 1998 5c Leeuwenburgh MA, Van der Marel GA, Overkleeft HS, van Boom JH. J. Carbohydr. Chem. 2003; 22: 549 Methyl protection: 5d Rech JC, Floreancig PE. Org. Lett. 2003; 5: 1495 6a Allwein S, Cox J, Howard B, Johnson H, Rainier J. Tetrahedron 2002; 58: 1997 6b Doddi VR, Kokatla HP, Pal AP. J, Basak RK, Vankar YD. Eur. J. Org. Chem. 2008; 5731 7a For acetyl protection in galactose series, see, for example: Šnajdr I, Parkan K, Hessler F, Kotora M. Beilstein J. Org. Chem. 2015; 11: 1392 In glucosamine series, see, for example: 7b McGarvey GJ, Schmidtmann FW, Benedum TE, Kizer DE. Tetrahedron Lett. 2003; 44: 3775 8 Patnam R, Juárez-Ruiz JM, Roy R. Org. Lett. 2006; 8: 2691 9 Nolen EG, Ezeh VC, Feeney MJ. Carbohydr. Res. 2014; 396: 43 10 Dondoni A, Mariotti G, Marra A. J. Org. Chem. 2002; 67: 4475 11 Reddy BG, Vankar YD. Angew. Chem. Int. Ed. 2005; 44: 2001 12 Delaunay T, Poisson T, Jubault P, Pannecoucke X. Eur. J. Org. Chem. 2014; 3341 Supplementary Material Supplementary Material Supporting Information (PDF) (opens in new window)
