Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2019; 51(12): 2484-2488
DOI: 10.1055/s-0037-1611800
DOI: 10.1055/s-0037-1611800
psp
Practical Gram-Scale Synthesis of Either α- or β-Anomer of C-Vinyl Glycosides
This work was supported by the Région des Pays de la Loire through the GlycoOuest program and the Ministère de l’Enseignement Supérieur et de la Recherche of France [Ph.D. fellowship (F.R.)].Further Information
Publication History
Received: 15 February 2019
Accepted after revision: 22 March 2019
Publication Date:
15 April 2019 (online)

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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611800.
- Supporting Information
-
References
- 1 Yang G, Schmieg J, Tsuji M, Franck RW. Angew. Chem. Int. Ed. 2004; 43: 3818
- 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
- 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
- 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
- 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
For example, see:
Benzyl protection:
Methyl protection:
In glucosamine series, see, for example: