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Synthesis 2007(2): 294-298
DOI: 10.1055/s-2006-958943
DOI: 10.1055/s-2006-958943
PAPER
© Georg Thieme Verlag Stuttgart · New YorkConversion of Glycals to 1-Azido-2-iodo Sugars Using N-Iodosuccinimide/Sodium Azide or Potassium Iodide/Oxone Reagent Systems: Application in the Synthesis of Methyl N-Acetyl-α-d-lividosaminide
Weitere Informationen
Received
11 September 2006
Publikationsdatum:
14. Dezember 2006 (online)
Publikationsverlauf
Publikationsdatum:
14. Dezember 2006 (online)

Abstract
Glycals are readily converted into the corresponding 2-deoxy-2-iodoglycosyl azides, in good to excellent yields in a short time, upon treatment with N-iodosuccinimide/sodium azide or potassium iodide/Oxone reagent systems. One of these 1-azido-2-iodo sugars was converted into methyl N-acetyl-α-d-lividosaminide.
Key words
glycals - N-iodosuccinimide - sodium azide - potassium iodide - Oxone - 1-azido-2-iodo sugar - methyl N-acetyl-α-d-lividosaminide
- 1
Banoub J.Boullanger P.Lafont D. Chem. Rev. 1992, 92: 1167 - 2
Lafont D.Guilloux P.Descotes G. Carbohydr. Res. 1989, 193: 61 - 3
Lafont D.Descotes G. Carbohydr. Res. 1987, 166: 195 - 4
Kirschning A.Monenschein H.Schmeck C. Angew. Chem. Int. Ed. 1999, 38: 2594 - 5
Kirschning A.Hashem MA.Monenschein H.Rose L.Schoning K.-U. J. Org. Chem. 1999, 64: 6522 - 6a
Reddy BG.Madhusudanan KP.Vankar YD. J. Org. Chem. 2004, 69: 2630 - 6b
Rani S.Agarwal A.Vankar YD. Tetrahedron Lett. 2003, 44: 5001 - 6c
Reddy BG.Vankar YD. Tetrahedron Lett. 2003, 44: 4765 - 6d
Rani S.Vankar YD. Tetrahedron Lett. 2003, 44: 907 - 6e
Pachamuthu K.Das J.Gupta A.Schmidt RR.Vankar YD. Eur. J. Org. Chem. 2002, 1479 - 6f
Pachamuthu K.Vankar YD. J. Org. Chem. 2001, 66: 7511 - 6g
Gupta A.Vankar YD. Tetrahedron 2000, 56: 8525 - 7a
Vankar YD.Kumaravel G. Tetrahedron Lett. 1984, 25: 233 - 7b
Agarwal A.Rani S.Vankar YD. J. Org. Chem. 2004, 69: 6137 - 7c
Babu RS.Zhou M.O’Doherty GA. J. Am. Chem. Soc. 2004, 126: 3428 - 7d
Saeed M.Ilg T.Schick M.Abbas M.Voelter W. Tetrahedron Lett. 2001, 42: 7401 - 7e
Harris JM.Keranen MD.Nguyen H.Young VG.O’Doherty GA. Carbohydr. Res. 2000, 328: 17 - 8
Curini M.Epifano F.Marcotullio MC.Rosati O. Tetrahedron Lett. 2002, 43: 1201 - 9
de Guchteneere E.Fattori D.Vogel P. Tetrahedron 1992, 48: 10603 - 10a
Tsuchiya T.Watanabe I.Yoshida M.Nakamura F.Usui T.Kitamura M.Umezawa S. Tetrahedron Lett. 1978, 19: 3365 - 10b
Rosenthal A.Catsoulacos P. Can. J. Chem. 1969, 47: 2748 - 10c
Arita H.Furukawa K.Matsushima Y. Bull. Chem. Soc. Jpn. 1972, 45: 3614 - 10d
Brewer CL.Guthrie RD. J. Chem. Soc., Perkin Trans. 1 1974, 657 - 10e
Haskell TH.Woo PWK.Watson DR. J. Org. Chem. 1977, 42: 1302 - 10f
Nair V.Sinhababu AK. J. Org. Chem. 1978, 43: 5013 - 10g
Ravindran B.Deshpande SG.Pathak T. Tetrahedron 2001, 57: 1093 - 10h
Reddy BG.Vankar YD. Tetrahedron Lett. 2003, 44: 4765 - 11a
Jager V.Schohe R. Tetrahedron 1984, 40: 2199 - 11b
Fattori D.de Guchteneere E.Vogel P. Tetrahedron Lett. 1989, 30: 7415 - 11c
de Guchteneere E.Fattori D.Vogel P. Tetrahedron 1992, 48: 10603 - 12
Fraser-Reid B.Tam SY.-K.Radatus B. Can. J. Chem. 1975, 53: 2005 - 13
Yamasaki T.Kubota Y.Tsuchiya T.Umezawa S. Bull. Chem. Soc. Jpn. 1976, 49: 3190