Stereoselective entry into the d-GalNAc series starting from the d-Gal one: a new access to N-acetyl-d-galactosamine and derivatives thereof

Carbohydrate Research

Volumn 344, Issue 3, 2009, Pages 298-303

  Guazzelli, Lorenzo ^a   Catelani, Giorgio ^a   D'Andrea, Felicia ^a   Giannarelli, Alessia ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

d Galactopyranosides; Amination with inversion; Epimerization; Lactose; N Acetyl d galactosamine

Indexed keywords

AMINATION WITH INVERSION; ANOMERIC DEPROTECTION; DE PROTECTIONS; DIMETHYL ACETALS; EPIMERIZATION; GALACTOPYRANOSIDE; ISOPROPYLIDENE; LACTOSE; METHOXY; N-ACETYL-D-GALACTOSAMINE; STEREO-SELECTIVE; STEREOSELECTIVE PREPARATIONS;

AMINATION; AMINES; DERIVATIVES; POLYSACCHARIDES; STEREOSELECTIVITY;

SUGARS;

4 METHOXYPHENYL 3,4 O ISOPROPYLIDENE 6 O (1 METHOXY 1 METHYLETHYL) BETA DEXTRO GALACTOPYRANOSIDE; DISACCHARIDE; GALACTOSE; LACTOSE; N ACETYLGALACTOSAMINE; PYRANOSIDE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; EPIMERIZATION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

ACETYLGALACTOSAMINE; ACETYLGLUCOSAMINE; AMINATION; CARBOHYDRATE SEQUENCE; GALACTOSE; GALACTOSIDES; MOLECULAR SEQUENCE DATA; STEREOISOMERISM;

EID: 59849087280     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2008.11.018     Document Type: Article

References (37)

1. Attolino E., Bonaccorsi F., Catelani G., and D'Andrea F. Carbohydr. Res. 343 (2008) 2545-2556
2. Levene P.A., and La Forge F.B. J. Biol. Chem. 18 (1914) 123-130
3. Jeanloz R.W. In: Pigman W., and Horton D. (Eds). The Carbohydrates. Chemistry and Biochemistry vol. IIB (1970), Academic Press, New York 590-625
4. Hanisch F.-G., and Müller S. Glycobiology 10 (2000) 439-449
5. Sharon N. Complex Carbohydrates. Their Chemistry, Biosynthesis, and Functions (1975), Addison-Wesley
6. Krist P., Herkommerová-Rajnochová E., Rauvolfová J., Semeňuk T., Vavrušková P., Pavlíček J., Bezouška K., Petruš L., and Křen V. Biochem. Biophys. Res. Commun. 287 (2001) 11-20
7. Selected representative reports:. Gross P.H., Du Bois F., and Jeanloz R.W. Carbohydr. Res. 4 (1967) 244-248
8. Hill J., and Hough L. Carbohydr. Res. 8 (1968) 398-404
9. Fukuda Y., Sasai H., and Suami T. Bull. Soc. Chim. Jpn. 55 (1982) 1574-1578
10. McGeary R.P., Wright K., and Toth I. J. Org. Chem 66 (2001) 5102-5105
11. Misra A.K., Fukuda M., and Hindsgault O. Bioorg. Med. Chem. Lett. 11 (2001) 2667-2669
12. Ito N., Tokuda Y., Ohba S., and Sugai T. Bull. Soc. Chim. Jpn. 77 (2004) 1181-1186
13. Hederos M., and Konradsson P.J. J. Carbohydr. Chem. 24 (2005) 297-320
14. Paulsen H., Kolář C., and Stenzel W. Angew. Chem. 88 (1976) 1532-1568
15. Lemieux R.U., and Ratcliffe R.M. Can. J. Chem. 57 (1979) 1244-1251
16. Griffith D.A., and Danishefsky S.J. J. Am. Chem. Soc. 112 (1990) 5811-5819
17. Liu J., and Gin D.Y. J. Am. Chem. Soc. 124 (2002) 9789-9797
18. Kuhn R., and Kirschenlohr W. Angew. Chem. 67 (1955) 786
19. Brossmer R. Methods Carbohydr. Chem. 1 (1962) 216-221
20. Wrodnigg T.M., Lundt I., and Stütz A.E. J. Carbohydr. Chem. 25 (2006) 33-41
21. Attolino E., Bonaccorsi F., Catelani G., D'Andrea F., Křenel K., Bešouska K., and Křen V. J. Carbohydr. Chem. 27 (2008) 156-171
22. Van den Nieuwenhof I.M., Schiphorst W.E., and Van den Eijnden D.H. FEBS Lett. 459 (1999) 377-380
23. Neeleman A.P., and Van den Eijnden D.H. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 10111-10116
24. Attolino E., Catelani G., and D'Andrea F. Eur. J. Org. Chem. 23 (2006) 5279-5292
25. David S., Malleron A., and Dini C. Carbohydr. Res. 188 (1989) 193-200
26. Vatèle J.-M., and Hanessian S. In: Hanessian S. (Ed). Preparative Carbohydrate Chemistry (1997), M. Dekker, New York 127-149
27. Bock K., and Thøgersen H. Ann. Rep. NMR Spectrosc. 13 (1982) 1-57
28. Izumi K. Carbohyd. Res. 170 (1987) 19-25
29. Thijssen M.J.L., van Rijswijk M.N., Kamerling J.P., and Vliegenthart J.F.G. Carbohydr. Res. 306 (1998) 93-109
30. Jacquinet J.-C. Carbohydr. Res. 341 (2006) 1630-1644
31. Zhang Z., and Magnusson G. J. Org. Chem. 61 (1996) 2383-2393
32. Grundler G., and Schmidt R. Liebigs Ann. Chem. (1984) 1826-1847
33. Vasella A., Witzig C., Chiara J.-L., and Martin-Lomas M. Helv. Chim. Acta 74 (1991) 2073-2077
34. For glycosyl trichloroacetimidates:. Payne R.J., Ficht S., Tang S., Brik A., Yang Y.-Y., Case D.A., and Wong C.-H. J. Am. Chem. Soc. 129 (2007) 13527-13536
35. For glycosyl N-phenyl-trifluoroacetimidates:. Adinolfi M., Iadonisi A., Ravidà A., and Schiattarella M. J. Org. Chem. 70 (2005) 5316-5319
36. For a glycosyl fluoride:. Grigalevicius S., Chierici S., Renaudet O., Lo-Man R., Dériaud E., Leclerc C., and Dumy P. Bioconjugate Chem. 16 (2005) 1149-1159
37. For a glycosyl diphenylphosphate:. Tsuda T., Nakamura S., and Hashimoto S. Tetrahedron 60 (2004) 10711-10737