A Facile Synthesis of Glycosyl Hydroxylamines

REFERENCES

• Spevak , W. , Dasgupta , F. , Hobbs , C. J. and Nagy , J. O. 1996 . J. Org. Chem. , 61 : 3417 – 3422 .
   Google Scholar
• Keynes , M. K. , Earle , M. A. , Sudharshan , M. and Hultin , P. G. 1996 . Tetrahedron , 52 : 8685 – 8702 .
   Google Scholar
• Linek , K. , Alfoldi , J. and Durindova , M. 1992 . Chem. Pap. , 47 : 247 – 250 .
   Google Scholar
• Laschat , S. and Kunz , H. 1991 . J. Org. Chem. , 56 : 5883 – 5889 .
   Web of Science ®Google Scholar
• Kunz , H. 1995 . Pure. Appl. Chem. , 67 : 1627 – 1635 .
   Web of Science ®Google Scholar
• Cipolla , L. , Lay , L. , Nicotra , F. , Pangrazio , C. and Panza , L. 1995 . Tetrahedron , 51 : 4679 – 4690 .
   Web of Science ®Google Scholar
• Kunz , H. and Ruck , K. 1993 . Angew. Chem. Int. Ed. Engl. , 32 : 336 – 358 .
   Web of Science ®Google Scholar
• Lockhoff , O. 1991 . Angew. Chem. Int. Ed. Engl. , 30 : 1611 – 1620 .
   Web of Science ®Google Scholar
• Somsak , L. , Sos , E. , Gyorgydeak , Z. , Praly , J.-P. and Descotes , G. 1996 . Tetrahedron , 52 : 9121 – 9136 .
   Google Scholar
• Praly , J.-P. , Bonnevie , C. , Haug , P. and Descotes , G. 1996 . Tetrahedron , 52 : 9057 – 9068 .
   Web of Science ®Google Scholar
• Sano , H. , Mio , S. , Kitagawa , J. , Shindou , M. , Honma , T. and Sugai , S. 1995 . Tetrahedron , 51 : 12563 – 12572 .
   Web of Science ®Google Scholar
• Praly , J.-P. , Senni , D. , Faure , R. and Descotes , G. 1995 . Carbohydr. Chem. , 268 : 85 – 92 .
   Google Scholar
• Gyorgydeak , Z. 1995 . Carbohydr. Chem. , 268 : 85 – 92 .
   Google Scholar
• Giuliano , R. M. , Davies , R. S. and Boyko , W. J. 1994 . J. Carbohydrate Chem. , 13 : 1135 – 1143 .
   Web of Science ®Google Scholar
• Gyorgydeak , Z. , Szilagyi , L. and Paulsen , H. 1993 . J. Carbohydrate Chem. , 12 : 139 – 163 .
   Web of Science ®Google Scholar
• Avalos , M. , Babiano , R. , Cintas , P. , Duran , C. J. , Jimenez , J. L. and Palacios , J. C. 1995 . Tetrahedron , 51 : 8043 – 8056 . and references cited therein. For the synthesis of similar substrates see: Beaupere, D.; Meslouti, A.E.; Lelievre, Ph.; Uzan, R., Tetrahedron Lett., 1995, 36, 5347—5348. Kovacs, J.; Pinter, I.; Abeln, D.; Kopf, J.; Koll, P., Carbohydr. Res., 1994, 257, 97—106. Kovacs, J.; Pinter, I.; Lendering, U.; Koll, P., Carbohydr. Res., 1991, 210, 155—156.
   Web of Science ®Google Scholar
• Vasella , A. 1977 . Helv. Chim. Acta , 60 : 426 – 446 .
   Web of Science ®Google Scholar
• We refer in this communication to anomeric glycosyl hydroxylamines. For a synthesis of non-anomeric hydroxyamino sugars see: Tronchet J. M.J. Habashi F. Fasel J.-P. Zosimo-Landolfo G. Barbalat-Rey F. Moret G. Helv. Chim. Acta 1986 69 1132 1136
   Google Scholar
• Kartha , K. P.R. 1986 . Tetrahedron Lett. , 27 : 3415 – 3416 .
   Web of Science ®Google Scholar
• Borch , R. F. , Berstein , M. D. and Durst , H. D. 1971 . J. Am. Chem. Soc. , 93 : 2897 – 2904 .
   Web of Science ®Google Scholar
• Dondoni , A. , Franco , S. , Junquera , F. , Merchan , F. L. , Merino , P. and Tejero , T. 1994 . Synth. Commun. , 24 : 2537 – 2550 .
   Web of Science ®Google Scholar
• Franco , S. , Merchan , F. L. , Merino , P. and Tejero , T. 1995 . Synth. Commun. , 25 : 2275 – 2284 .
   Web of Science ®Google Scholar
• A small amount of starting aldose (≈5%) was recovered.
   Google Scholar
• It has been reported that pyranoses are not adequate substrates for condensation with nucleophiles such as phosphoranes. See, for instance: Dondoni A. Marra A. Tetrahedron Lett. 1993 34 7327 7330
   Google Scholar
• Huber , R. and Vasella , A. 1987 . Helv. Chim. Acta. , 70 : 1461 – 1476 .
   Web of Science ®Google Scholar
• Ohrui , H. , Jones , G. H. , Moffatt , J. G. , Maddox , M. L. , Christensen , A. T. and Byram , S. K. 1975 . J. Am. Chem. Soc. , 97 : 4602 – 4613 .
   PubMed Web of Science ®Google Scholar
• Collins , P. and Ferrier , R. 1995 . Monosaccharides , Chichester : John Wiley .
   Google Scholar
• Merino , P. , Franco , S. , Merchan , F. L. and Tejero , T. unpublished results.
   Google Scholar
• Barker , R. and Fletcher , H. G. 1961 . J. Org. Chem. , 26 : 4605 – 4609 .
   Web of Science ®Google Scholar
• Koto , S. , Morishima , N. , Miyata , Y. and Zen , S. 1976 . Bull. Chem. Soc. Jpn. , 49 : 2639 – 2640 .
   Web of Science ®Google Scholar