Summary
An improved procedure was developed for the zinc-mediated fragmentation of protected and unprotected methyl 6-deoxy-6-iodo-hexopyranosides. The method employs sonication of the iodoglycoside with zinc dust in a THF/H2O mixture.
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References
Bernet B, Vasella A (1979) Helv Chim Acta 62: 1990
Ferrier RJ, Furneaux RH, Prasit P, Tyler PC, Brown KL, Gainsford GJ, Diehl JW (1983) J Chem Soc Perkin Trans 1, 1621
] Nakata M, Akazawa S, Kitamura S, Tatsuta K (1991) Tetrahedron Lett 32: 5363
] Dransfield PJ, Moutel S, Shipman M, Sik V (1999) J Chem Soc Perkin Trans 1, 3349
Désiré J, Prandi J (2000) Eur J Org Chem 3075
Bernotas RC, Papandreou G, Urbach J, Ganem B (1990) Tetrahedron Lett 31: 3393
Villalobos A, Danishefsky SJ (1990) J Org Chem 55: 2776;
] Fürstner A, Baumgartner J (1993) Tetrahedron 49: 8541
Kobori Y, Myles DC, Whitesides GM (1992) J Org Chem 57: 5899
Kleban M, Kautz U, Greul J, Hilgers P, Kugler R, Dong H-Q, Jäger V (2000) Synthesis 1027
Ovaa H, Codée JDC, Lastdrager B, Overkleeft HS, van der Marel GA, van Boom JH (1999) Tetrahedron Lett 40: 5063
Fürstner A, Weidmann H (1990) J Org Chem 55: 1363;
] Fürstner A, Jumbam D, Teslic J,Weidmann H (1991) J Org Chem 56: 2213
Fürstner A, Baumgartner J, Jumbam DN (1993) J Chem Soc Perkin Trans 1, 131
Hyldtoft L, Poulsen CS, Madsen R (1999) Chem Commun 2101
] Hyldtoft L, Madsen R (2000) J Am Chem Soc 122: 8444
Stout EI, Doane WM, Trinkus VC (1976) Carbohydr Res 50: 282
Fürstner A, Weidmann H (1989) J Org Chem 54: 2307
de Raadt A, Ebner M, Ekhart CW, Fechter M, Lechner A, Strobl M, Stütz AE (1994) Catalysis Today 22: 549
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© 2002 Springer-Verlag Wien
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Skaanderup, P.R., Hyldtoft, L., Madsen, R. (2002). Zinc-Mediated Fragmentation of Methyl 6-Deoxy-6-iodo-hexopyranosides. In: Schmid, W., Stütz, A.E. (eds) Timely Research Perspectives in Carbohydrate Chemistry. Springer, Vienna. https://doi.org/10.1007/978-3-7091-6130-2_7
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DOI: https://doi.org/10.1007/978-3-7091-6130-2_7
Publisher Name: Springer, Vienna
Print ISBN: 978-3-7091-7289-6
Online ISBN: 978-3-7091-6130-2
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