Regioselectivity shift from β-(1→6)- to β-(1→3)-glycosylation of non-protected methyl β-D-galactopyranosides using the stannylene activation method

Tetrahedron Letters

Volumn 44, Issue 26, 2003, Pages 4881-4885

  Kaji, Eisuke ^a   Shibayama, Keigo ^a   In, Kazusada ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; GLUCOSYL BETA (1-3) GALACTOSE; GLUCOSYL BETA (1-6) GALACTOSE; METHYL BETA DEXTRO GALACTOPYRANOSIDE; PYRANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DEPROTECTION REACTION; GLYCOSYLATION; STEREOCHEMISTRY;

EID: 0038579450     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01095-5     Document Type: Article

References (23)

1. Garegg P.J. Hanessian S. Preparative Carbohydrate Chemistry. 1997;53-67 Marcel Dekker, New York.
2. Tsuda Y., Haque M.E., Yoshimoto K. Chem. Pharm. Bull. 31:1983;1612.
3. Haque M.E., Kikuchi T., Yoshimoto K., Tsuda Y. Chem. Pharm. Bull. 33:1985;2243.
4. David, S. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1997; Chapter 4, p. 69.
5. Grindley T.B. Adv. Carbohydr. Chem. Biochem. 53:1998;17.
6. Martinelli M.J., Vaidyanathan R., Pawlak J.M., Nayyar N.K., Dhokte U.P., Doecke C.W., Zollars L.M.H., Moher E.D., Khau V.V., Kosmrlj B. J. Am. Chem. Soc. 124:2002;3578.
7. Garegg P.J., Maloisel J.-L., Oscarson S. Synthesis. 1995;409.
8. Kartha R.K.P., Kiso M., Hasegawa A., Jennings H.L. J. Chem. Soc., Perkin Trans. 1. 1995;409.
9. Kaji E., Harita N. Tetrahedron Lett. 41:2000;53. and references cited therein.
10. For example, sulfoglucuronyl paragloboside (SGPG) comprising GlcA-β-(1→3)-Gal unit is relevant to a neural cell adhesion molecule (N-CAM) and human natural killer cell (HNK-1): (a) McGarry, R. C.; Helfand, S. L.; Quarles, R. H.; Roder, J. C. Nature 1983, 306, 376; (b) Kruse, J.; Mailhammer, R.; Wernecke, H.; Faissner, A.; Sommer, I.; Goridis, C.; Schachner, M. Nature 1984, 311, 153.
11. For example, sulfoglucuronyl paragloboside (SGPG) comprising GlcA-β-(1→3)-Gal unit is relevant to a neural cell adhesion molecule (N-CAM) and human natural killer cell (HNK-1): (a) McGarry, R. C.; Helfand, S. L.; Quarles, R. H.; Roder, J. C. Nature 1983, 306, 376; (b) Kruse, J.; Mailhammer, R.; Wernecke, H.; Faissner, A.; Sommer, I.; Goridis, C.; Schachner, M. Nature 1984, 311, 153.
12. van Boeckel C.A.A., Beetz T., Kock-van Dalen A.C., van Bekkum H. Recl. Trav. Chim. Pay-Bas. 106:1987;596.
13. Kaji E., Lichtenthaler F.W., Osa Y., Takahashi K., Zen S. Bull. Chem. Soc. Jpn. 68:1995;2401. and the preceding papers cited therein.
14. 5) and Δδ value of methyl β-D-galactopyranoside ( 5 ), glucosyl-β-(1→6)-galactoside ( 7 ), and glucosyl-β-(1→3)-galactoside ( 10 ) are listed as follows. For example, Δδ of C-6 between compounds 5 and 7 shows +7.8 ppm, whereas Δδ value of other non-glycosylated carbons are in the range of +0.1∼-1.6 ppm. The β-configuration of the newly formed intersaccharide linkage of 7 and 10 is apparent from the relatively large coupling constant (8.0 Hz) between H-1′ and H-2′.
15. Equilibrium of stannylated sugars including their dimeric structures has been proposed: Grindley, T. B.; Thangarasa, R. Can. J. Chem. 1990, 68, 1007. For simplification we showed only monomeric structures.
16. Paulsen H. Angew. Chem., Int. Ed. Engl. 21:1982;155.
17. Nagashima N., Ohno M. Chem. Pharm. Bull. 39:1991;1972. and references cited therein.
18. Crombez-Robert C., Benazza M., Frechou C., Demailly G. Carbohydr. Res. 307:1998;355.
19. David S., Thieffry A., Veyrieres A. J. Chem. Soc., Perkin Trans. 1. 1981;1796.
20. Alais J., Maranduba A., Veyrieres A. Tetrahedron Lett. 24:1983;2383.
21. Kohata, K.; Abbas, S. A.; Matta, K. L. Carbohydr. Res. 1984, 132, 127: methyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside is prepared from 5 in 49% yield over three steps.
22. The recovered bromide was identified on the basis of its MS and NMR spectra, indicating no conversion into the corresponding fluoride.
23. A similar ion pair mechanism involving penta-coordinated tin atom has been proposed in the regioselective benzylation of aliphatic diols by Ohno et al. See Ref. 12a.