Synthesis of carbohydrate-containing dendrimers. 5. Preparation of dendrimers using unprotected carbohydrates

Tetrahedron Letters

Volumn 38, Issue 38, 1997, Pages 6767-6770

  Jayaraman, Narayanaswamy ^a   Stoddart, J Fraser ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMER;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL STRUCTURE; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030852402     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01548-7     Document Type: Article

References (18)

1. Address for correspondence after October 1, 1997: Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095-1569, USA.
2. For authoritative reviews and a monograph on dendrimers, see: a) D.A. Tomalia, H.D. Durst, in Top. Curr. Chem. 1993, 165, 193-313;
3. b) J.M.J. Fréchet, Science, 1994, 263, 1710-1715;
4. c) G.R. Newkome, C.N. Moorefield, F. Vögtle, Dendritic Molecules. Concepts, Syntheses, Perspectives, VCH, Weinheim, 1996.
5. For examples of the encapsulation of guest molecules inside the dendritic structures, see: a) A.M. Naylor, W.M. Goddard III, G.E. Keifer, D.A. Tomalia, J. Am. Chem. Soc. 1989, 111, 339-2341;
6. b) C.J. Hawker, K.L. Wooley, J.M.J. Fréchet, J. Chem. Soc., Perkin Trans., 1, 1993, 1287-1297;
7. c) J.F.G.A. Jansen, E.M.M. de Brabander-van den Berg, E.W. Meijer, Science, 1994, 266, 1226-1229;
8. d) J.F.G.A. Jansen, E.W. Meijer, E.M.M. de Brabander-van den Berg, J. Am. Chem. Soc. 1995, 117, 4417-4418.
9. a) P.R. Ashton, S.E. Boyd, C.L. Brown, N. Jayaraman, S.A. Nepogodiev, J.F. Stoddart, Chem. Eur. J. 1996, 2, 1115-1128;
10. b) P.R. Ashton, S.E. Boyd, C.L. Brown, N. Jayaraman, J.F. Stoddart, Angew. Chem. Int. Ed. Engl. 1997, 36, 732-735;
11. c) N. Jayaraman, S.A. Nepogodiiev, J.F. Stoddart, Chem. Eur. J. 1997, In Press.
12. 2O (1:1) for ~15 h to obtain the free amino group tethered glycosides 1 and 2 as glassy solids (overall yields >70%).
13. 2), 69.4 (C-4), 72.6 (C-2), 73.2 (C-3), 75.5 (C-5), and 102.6 (C-1).
14. 2, before being dried thoroughly to obtain the N-hydroxysuccinimide triester 3 in 74% yield.
15. 2), 69.4 (C-4), 72.7 (C-2), 73.1 (C-3), 75.5 (C-5), 102.3 (C-1), 132.3, 136.7 (aromatic), and 171.4, 174.1 (CONH).
16. 2C(quat)), 72.5 (C-2), 73.2 (C-3), 75.5 (C-5), and 102.9 (C-1).
17. 2C(quat)), 69.5 (C-4), 72.6 (C-2), 73.3 (C-3), 75.7 (C-5), 103.0 (C-1), 133.5, 138.0 (aromatic), and 170.2, 174.1 (CONH).
18. Recently, the use of unprotected carbohydrates to modify pre-formed dendrimer (PAMAM) structures, with thiourea bridges, has been reported. See: C. Kieburg, T.K. Lindhorst, Tetrahedron Lett. 1997, 38, 3885-3888.