An easy access to anomeric glycosyl amides and imines (Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides

Tetrahedron

Volumn 57, Issue 21, 2001, Pages 4609-4621

  Kovács, László ^a   Osz, Erzsébet ^b   Domokos, Valéria ^a   Holzer, Wolfgang ^c   Györgydeák, Zoltán ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b UNIVERSITY OF PÉCS   (Hungary)

^c UNIVERSITY OF VIENNA   (Austria)

Author keywords

Glycosyl amides; Glycosyl imides; Glycosyl imines; Staudinger reaction

Indexed keywords

AMIDE; AZIDE; CARBOXYLIC ACID DERIVATIVE; GLYCOPYRANOSIDE; IMINE; PHOSPHINE DERIVATIVE; SCHIFF BASE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SYNTHESIS;

EID: 0037962016     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)00380-5     Document Type: Article

References (129)

1. Paulsen H., Pflughaupt K.W. Glycosylamines. Pigman W., Horton D. The Carbohydrates, Chemistry and Biochemistry. 1980;881-927 Academic, New York.
2. Lockhoff O. Angew. Chem. 103:1991;1637-1647. Angew. Chem., Int. Ed. Engl. 1991, 30, 1639-1647.
3. Avalos M., Babiano R., Carratero M.J., Cintas P., Higes F.J., Jiménez J.L., Palacios J.C. Tetrahedron. 54:1998;615-628.
4. Timmers C.M., Turner J.J., Ward C.M., van der Marel G.A., Kouwijzer M.L.C.E., Grootenhuis P.D.J., Boom J.H. Chem. Eur. J. 3:1997;920-930.
5. Rottman H., Synstad B., Eijsink V., Peter M.G. J. Org. Chem. 1999;2293-2297. and references cited therein.
6. Varki A. Glycobyiology. 3:1993;97-130.
7. Feizi T., Bundle D. Curr. Opin. Struct. Biol. 4:1994;673.
8. Bill R.M., Flitsch S.L. Chem. Biol. 3:1996;145-149.
9. Arsequell G., Valencia G. Tetrahedron: Asymmetry. 10:1999;3045-3094. and references cited therein.
10. Bahl O.P. Bahl O.P. An Introduction to Glycoproteins. 1992;1 Dekker, New York.
11. Roberge J.Y., Beebe X., Danishefsky S.J. J. Am. Chem. Soc. 120:1998;3915-3927.
12. Kobata A. Acc. Chem. Res. 26:1993;319-323.
13. Opdenakker G., Rudd P.M., Ponting C.P., Dwek R.A. FASEB J. 7:1993;1330-1337.
14. Garg H., Jeanloz R.W. Adv. Carbohydr. Chem. Biochem. 43:1985;135-186.
15. Paulsen H. Angew. Chem. 102:1990;851-867.
16. Kunz H. Pure Appl Chem. 65:1993;1223-1232.
17. Cohen-Anisfeld S.T., Lansbury P.T. Jr. J. Chem. Soc. 115:1993;10531-10537.
18. Meldal M. Lee Y.C., Lee R.T. Neoglucoconjugates: Preparation and Application. 1994;145-198 Academic, Orlando.
19. Wong C.H., Halcomb R.L., Ichikawa Y., Kajimoto T. Angew. Chem. 107:1995;453-474. and 569-593. Angew. Chem., Int. Ed. Engl. 1995, 34, 412-432 and 521-546.
20. Garg H.G., von dem Bruch K., Kunz H. Carbohydr. Chem. Biochem. 277:1994;310.
21. Peters S. Recent Developments in Glycopeptide Synthesis. 1996;Harwood. pp 352-377.
22. Vetter D., Tumelty D., Singh S.K., Gallop M.A. Angew. Chem. 117:1995;94-97. Angew. Chem. Int. Ed. Engl. 1995, 34, 60-62.
23. Holm B., Linse S., Kihlberg J. Tetrahedron. 54:1998;11995-12006.
24. Taylor C.M. Tetrahedron. 54:1998;11317-11362.
25. Jobron L., Hummel G. Angew. Chem. 112:2000;1704-1707. Angew. Chem., Int. Ed. Engl. 2000, 39, 1621-1624.
26. Seitz O. Chembiochem. 1:2000;214-246.
27. Bognár R., Somogyi L. Chem. Ber. 99:1966;1032-1039.
28. Khorlin A.Y., Zhurabyan S.E., Macharadze R.E. Carbohydr. Res. 85:1980;201-208.
29. Günther W., Kunz H. Angew. Chem. 102:1990;1068-1069. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050-1051.
30. Kassab R., Félix C., Parrot-Lopez H., Bonaly R. Tetrahedron Lett. 38:1997;7555-7558.
31. Kassab R., Fenet B., Parrot-Lopez H. Tetrahedron Lett. 41:2000;877-881.
32. Horner L., Gross A. Justus Liebigs Ann. Chem. 59:1953;117-134.
33. García J., Urpí F., Vilarrasa J. Tetrahedron Lett. 25:1984;4841-4844.
34. Zaloom J., Calandra M., Roberts D.C. J. Org. Chem. 50:1985;2601-2603.
35. Ghosh S.K., Singh M., Mamdapur V.R. Tetrahedron Lett. 33:1992;805-808.
36. Bosch I., Romea P., Urpí F., Vilarrasa J. Tetrahedron Lett. 33:1992;4671-4674.
37. Molina P., Alajarín M., López-Leonanrdo C., Alcántara J. Tetrahedron. 49:1993;5153-5168.
38. Frøyen P. Phosphorus, Sulfur, Silicon Relat. Elem. 78:1993;161-173.
39. Bosch I., Urpí F., Vilarrasa J. J. Chem. Soc., Chem. Commun. 1995;91-92.
40. Shalev D.E., Chiacchiera S.M., Radkovsky A.E., Kosower E.M. J. Org. Chem. 61:1996;1689-1701. and references cited therein.
41. Ghosh S.K., Verma R., Ghosh U., Mamdapur V.R. Bull. Chem. Soc. Jpn. 69:1996;1705-1711.
42. Afonso C.A.M. Tetrahedron Lett. 36:1995;8857-8858.
43. Trost B.M., Stenkamp D., Pulley S.R. Chem Eur. J. 1995;568-572.
44. Kotsuki H., Ohishi T., Araki T. Tetrahedron Lett. 38:1997;2129-2132.
45. Ariza X., Urpí F., Vildomat C., Vilarrasa J. Tetrahedron Lett. 39:1998;9101-9102.
46. Afonso C.A.M. Synth. Commun. 28:1998;261-276.
47. Malkinson J.P., Falconer R.A., Tóth I. J. Org. Chem. 65:2000;5249-5252.
48. Friedrich-Bosnitschek S., Waldmann H., Kunz H. J. Org. Chem. 54:1989;751-756.
49. Sahlberg C., Jansson A.M., Claesson A. Acta Chem. Scand. B. 42:1988;556-562.
50. Urpí F., Vilarrasa J. Tetrahedron Lett. 27:1986;4623-4624.
51. Maunier V., Boullanger P., Lafont D., Chevalier Y. Carbohydr. Res. 299:1997;49-57.
52. Strässler C., Heimgartner H. Helv. Chim. Acta. 80:1997;2058-2065.
53. Inazu T., Kobayasi K. Synlett. 1993;869-870.
54. García-López J.J., Santoyo-González F., Vargas-Berenguel A. Synlett. 1997;265-266.
55. Maunier V., Boullanger P., Lafont D. J. Carbohydr. Chem. 16:1997;231-235.
56. Holm B., Linse B., Kihlberg J. Tetrahedron. 54:1998;1195-1206.
57. Mizuno M., Muramoto I., Kobayashi K., Yaginuma H., Inazu T. Synthesis. 1999;162-165.
58. Mizuno M., Haneda K., Iguchi R., Muramoto I., Kawakami T., Aimoto S., Yamamoto K., Inazu T. J. Am. Chem. Soc. 121:1999;284-290.
59. García-López J.J., Santoyo-González F., Vargas-Berenguel A., Giménez- Martinez J. J. Chem. Eur. 5:1999;1775-1784.
60. Boullanger P., Maunier V., La-font D. Carbohydr. Res. 324:2000;97-106.
61. Snatzke G., Vlahov J. Liebigs. Ann. Chem. 1985;439-447.
62. Kahne D., Walker S., Cheng Y., van Engen D. J. Am. Chem. Soc. 111:1989;6881-6882.
63. Garcia B.A., Poole J.L., Gin D.Y. J. Am. Chem. Soc. 119:1997;7597-7598.
64. Vorbrüggen H. Acc. Chem. Res. 28:1995;509-520. and references cited therein.
65. Bennua-Skalmowsky B., Krolikiewicz K., Vorbrüggen H. Tetrahedron Lett. 36:1995;7845-7848.
66. Ratcliffe A.J., Fraser-Reid B. J. Chem. Soc., Perkin Trans. 1. 1990;747-750.
67. Ratcliffe J., Konradsson P., Fraser-Reid B. Carbohydr. Res. 216:1991;323-335.
68. Handlon A.L., Fraser-Reid B. J. Am. Chem. Soc. 115:1993;3796-3797.
69. cf. also: (d) Elias C., Gelpi M.E., Cadenas R.A. J. Carbohydr. Chem. 14:1995;1209-1216.
70. Avalos M., Babiano R., Durán C.J., Jiménez J.L., Palacios J.C. Tetrahedron Lett. 35:1994;477-480.
71. Avalos M., Babiano R., Cintas P., Durán C.J., Higes F.J., Jiménez J.L., López I., Palacios J.C. Tetrahedron. 53:1997;14463-14480.
72. Hodge J.E., Moy B.F. J. Org. Chem. 28:1963;2784-2789.
73. Plusquellec D., Brenner-Hénaff C., Léon-Ruaud P., Duquenoy S., Lefeuvre M., Wróblewski H. J. Carbohydr. Chem. 13:1994;737-751.
74. Micheel F., Freier R., Plate E., Hiller A. Chem. Ber. 85:1952;1092-1096.
75. Isbell H.S., Frush H.L. J. Org. Chem. 23:1958;1309-1319.
76. Isbell H.S., Frush H.L., Whistler R.L. BeMiller J.N. Methods Carbohydr. Chem. Vol VIII. 1980;255 Academic, New York.
77. Likhoshertsov L.M., Novikova O.S., Derevitskaya V.A., Kochetkov N.K. Izv. Akad. Nauk. SSSR, Ser. Khim. 1986;1663-1669. engl. 1512-1517.
78. Kallin E., Lönn H., Norberg T., Elofsson M.E. J. Carbohydr. Chem. 8:1989;597-611.
79. Ürge L., Kollát E., Hollósi M., Laczkó I., Wróblewski K., Thurin J., Ötvös L. Jr. Tetrahedron Lett. 32:1991;3445-3448.
80. Roy R., Leferriére C.A. J. Chem. Soc., Chem. Commun. 1990;1709-1711.
81. Kallin E., Lönn H., Norberg T., Lund T., Lundquist M. J. Carbohydr. Chem. 10:1991;377-386.
82. Manger I.D., Rademacher T.W., Dwek R.A. Biochemistry. 31:1992;10724-10732.
83. Christiansen-Brams I., Meldal M., Bock K. J. Chem. Soc., Perkin Trans. 1. 1993;1461-1471.
84. Vetter D., Gallop M.A. Bioconj. Chem. 6:1995;316-318.
85. Likhoshertsov L.M., Novikova O.S., Shibaev V.N., Kochetkov N.K. Izv. Akad. Nauk. SSSR, Ser. Khim. 1996;1848-1851.
86. Danishefsky S.J., Hu S., Cirillo P.F., Eckhardt M., Seeberger P.H. Chem. Eur. J. 3:1997;1617-1628.
87. Wang L.X., Tang M., Suzuki T., Kitajima K., Inoue Y., Inoue S., Fan J.Q., Lee Y.C. J. Am. Chem. Soc. 119:1997;11137-11146.
88. Mehta S., Meldal M., Duus J.O. J. Chem. Soc., Perkin Trans. 1. 1999;3213.
89. Wang Z.G., Zhang X.F., Live D., Danishefsky S.J. Angew. Chem. 112:2000;3798-3802. Angew. Chem., Int. Ed. Engl. 2000, 39, 3652-3655.
90. Ito Y., Gerz M., Nakahara Y. Tetrahedron Lett. 41:2000;1039-1042.
91. Paulsen H., Györgydeák Z., Friedmann M. Chem. Ber. 1974;1568-1578.
92. Perrin C.L., Armstrong K.B. J. Am. Chem. Soc. 115:1993;6825-6834.
93. Györgydeák Z., Szilágyi L., Paulsen H. J. Carbohydr. Chem. 12:1993;139-163. and references cited therein.
94. Paul B., Korytnyk W. Carbohydr. Res. 67:1978;457-468.
95. Linek K., Alföldi J., Defaye J. Carbohydr. Res. 164:1987;195-205.
96. Linek K., Alföldi J., Durindová M. Chem. Pap. 47:1993;247-250.
97. Timmers C.M., Turner J.J., Ward C.M., van der Marel G.A., Kouwijzer M.L.C.E., Grootehuis P.D.J., van Boom J.H. Chem. Eur. J. 3:1997;920-929.
98. Oertel K., Zech G., Kunz H. Angew. Chem. 112:2000;1489-1491. Angew. Chem., Int. Ed. Engl. 2000, 39, 1431-1433.
99. Ewing D.F., Goodby J.W., Guenais S., Letellier P., Mackenzie G., Piastrelli I., Plusquellec D. J. Chem. Soc., Perkin Trans. 1. 1997;3459-3463.
100. Camarasa M.J., Fernández-Resa P., Garcia-López M.T., de las Heras F.G., Méndez-Castillón P.P., Félix H.S. Synthesis. 1984;509-510.
101. Ledford B.E., Carreira E.M. J. Am. Chem. Soc. 117:1995;11811-11812.
102. Gololobov Y.G., Kasukhin L.F. Tetrahedron. 48:1992;1353-1406.
103. Johnson A.W., Kaska W.C., Ostoja Starzewski K.A., Dixon D.A. Ylides and Imines of Phosphorus. 1993;Wiley, New York. pp 403-483.
104. Wamhoff H., Richard G., Stölben S. Adv. Heterocycl. Chem. 64:1995;159-249.
105. García Fernández J.M., Mellet C.O., Diaz Pérez V.M., Fuentes J., Kovács J., Pintér I. Carbohydr. Res. 304:1997;261-270.
106. Storz T., Bernet B., Vasella A. Helv. Chim. Acta. 82:1994;2380-2412.
107. García Fernández J.M., Mellet C.O., Diaz Pérez V.M., Fuentes J., Kovács J., Pintér I. Carbohydr. Res. 304:1997;261-270.
108. Paulsen H., Györgydeák Z., Friedmann M. Chem. Ber. 107:1974;1590-1613.
109. Hiebl J., Zbiral E. Liebigs Ann. Chem. 1988;765-774.
110. Schwesinger R., Willaredt J., Schempler H., Keller M., Schmitt D., Fritz H. Chem. Ber. 127:1994;2435-2454.
111. Kaljurand I., Roodima T., Leito I., Koppel I.A., Schwesinger R. J. Org. Chem. 65:2000;6202-6208.
112. Sikora D., Gajda T. Tetrahedron. 56:2000;3755-3761.
113. Helferich B., Mitrowsky A. Chem. Ber. 85:1952;1-8.
114. Kovács J., Pintér I., Szego F., Tóth G., Messmer A. Acta Chim. Acad. Sci. Hung. 101:1979;7-16.
115. Kunz H., Sager W. Angew. Chem. 99:1987;595-597. Angew. Chem., Int. Ed. Engl. 1987, 26, 557-559.
116. Kunz H., Pfrengle W. J. Am. Chem. Soc. 110:1988;651.
117. Pfrengle W., Kunz H. J. Org. Chem. 54:1989;4261-4263.
118. Georg G.I., Mashava P.M., Akgün E., Milstead M.W. Tetrahedron Lett. 32:1991;3151-3154.
119. Kunz H., Pfrengle W., Sager W. Tetrahedron Lett. 30:1989;4109-4110.
120. Georg G.I., Akgün E., Mashava P.M., Milstead M.W., Ping H., Wu Z.J., Velde D.V. Tetrahedron Lett. 33:1992;2111-2114.
121. Rück-Braun K., Kunz H. Chiral Auxiliaries in Cycloadditions. 1999;Wiley-VCH, Weinheim.
122. Kunz H. Glycosamines as auxiliaries in Stereoselective Synthesis of Chiral Amino Compounds in Modern Amination Reaction. 1999;. Chapter 4.
123. Györgydeák Z. Acros Org. Acta. 1:(2):1995;74-75.
124. Cerezo A.S., Sproviero F., Deulofeu V., Delpy S. Carbohydr. Res. 7:1968;395-404.
125. Pacsu E., Janson J., Lindberg B. Methods Carbohydr. Chem. 2:1963;376-385.
126. Williams J.M., Jegou H., Langlois V., Zhang B-L. Carbohydr. Res. 245:1993;57-64.
127. Larm O. Carbohydr. Res. 43:1975;192-194. and references cited therein.
128. Gross H., Farkas I. Chem. Ber. 93:1960;95-99.
129. Lavielle S., Ling N.C., Guillemin R.C. Carbohydr. Res. 89:1981;221-228.