Synthesis of dendrimers containing 2,5-anhydro-D-mannitol as a chiral, tetrafunctional central core with C2 symmetry

Tetrahedron Letters

Volumn 39, Issue 50, 1998, Pages 9161-9164

  Rohde, Jason M ^a   Parquette, Jon R ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Asymmetry; Carbohydrates; Chiroptical properties; Dendrimers

Indexed keywords

CARBOHYDRATE; DENDRIMER; MANNITOL; POLYMER;

ARTICLE; CHIRALITY; CONFORMATION; NONHUMAN; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032506568     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02109-1     Document Type: Article

References (17)

1. (1) Introduction of a nonspecific, achiral pyridoxamine cofactor into the hydrophobic chiral cavity of adipocyte lipid binding protein (ALBP) afforded a catalyst that reductively aminates α-amino acids with high enantioselectivity; see: Kuang, H.; Brown, M.L.; Davies, R.R.; Young, E.C.; Distefano, M.D. J. Am. Chem. Soc. 1996, 118, 10702.
2. (2) For a recent discussion, see: Peerlings, H.W.I.; Meijer, E.W. Chem. Eur. J. 1997, 3, 1563.
3. (3) For a recent review: Matthews, O.W.; Shipway, A.N.; Stoddart, J.F. Prog. Poly. Sci. 1998, 23, 1.
4. (4) For an example of a dendrimer derived from a chiral, nonracemic central core see: Seebach, D.; Lapierre, J-M.; Greiveldinger, G.; Skobridis, K. Helv. Chim. Acta 1994, 77, 1673.
5. (5) For an example of a PAMAM-type dendrimer with a central core derived from glucose see: Dubber, M.; Lindhorst, T. K. Chem. Commun. 1998, 12, 1265.
6. (6) Structure and Reactivity in Aqueous Solution; Cramer, C.J.; Truhlar, D.O., Eds. ACS Symposium Series 568, American Chemical Society: Washington, DC, 1994.
7. (7) Horton, D.; Philips, K.D. Carbohydr. Res. 1973, 30, 367.
8. 3. Synthesis of the second and third generation dendrons bromides followed a method analogous to that described by Fréchet: Hawker, C.J.; Wooley, K.L.; Fréchet, J.M.J. J. Chem. Soc., Perkin Trans, 1 1993, 1287.
9. 133; C, 72.53; H, 5.59. Found: C, 72.24; H, 5.59.
10. n = 9264 PD = 1.038 (polystyrene standards)
11. (11) Chaumette, J-L.; Laufersweiler, M.J.; Parquette, J.R. J. Org. Chem., submitted.
12. (12) Peerlings, H.W.I.; Meijer, E.W. Eur. J. Org. Chem. 1998, 573.
13. (13) 3-8 exhibit UV absorptions bands at 250-260 nm; however, 8 exhibits an additional less intense absorption band at 308 nm. These electronic differences are not solely responsible for the change in rotation because the additional band at longer wavelength in 8 should lead to a slightly more negative rotation value which is not observed (see ref. 16, p. 999).
14. (14 Ciardelli, F.; Salvadori, P. Pure Appl. Chem., 1985, 57, 931.
15. (15) McElhanon, J.R.; McGrath, D.V. J. Am. Chem. Soc. 1998, 120, 1647.
16. (16) Eliel, E.L.; Wilen, S.H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; p 1076.
17. 37 (M) 2206.2; obsd. 2206.4.