Synthesis of the C-Glycoside of Methyl α-D-Altropyranosyl-(1→4)- α-D-glucopyranoside

Journal of Carbohydrate Chemistry

Volumn 22, Issue 7-8, 2003, Pages 671-683

  Denton, Richard W ^a   Mootoo, David R ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

Allose; Altrose; C glycoside; Conformation; Disaccharide; Glycomimetic

Indexed keywords

4 O TERT BUTYLDIPHENYLSILYL 1,2 O ISOPROPYLIDENE DEXTRO ERYTHRO PHENYLMONOTHIOHEMIACETAL; ACETAL DERIVATIVE; CARBENOID; CARBOHYDRATE DERIVATIVE; ETHER DERIVATIVE; GLUCOPYRANOSIDE; GLYCOSIDE; METHYL 2,3,6 TRI O BENZYL 4 (CARBOXYMETHYL) 4 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 4 (2,6 ANHYDRO 4,5 O ISOPROPYLIDENE 7 O TERT BUTYLDIPHENYLSILYL 1 DEOXY DEXTRO GLYCERO DEXTRO MANNOHEPTITOL 1 YL) 2,3,6 TRI O BENZYL 4 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 4 (2,6 ANHYDRO 7 O TERT BUTYLDIPHENYLSILYL 4,5 O ISOPROPYLIDENE 1,3 DIDEOXY DEXTRO RIBOHEPT 2 ENITOL 1 YL) 2,3,6 TRI O BENZYL 4 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHROMATOGRAPHY; CONFORMATION; CYCLIZATION; ESTERIFICATION; HYDROBORATION; PRECURSOR; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0346847622     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120026467     Document Type: Article

References (32)

1. Compain, P.; Martin, O.R. Carbohydrate mimetics-based glycosyltransferase inhibitors. Bioorg. Med. Chem. Lett. 2001, 9, 3077-3092.
2. Chapleur, Y. Carbohydrate Mimics, Concepts and Methods; Wiley-VCH: Weinheim, 1998.
3. Palcic, M.M.; Heerze, L.D.; Srivastava, O.P.; Hindsgaul, O. A bisubstrate analog inhibitor for α̃(1→2)-fucosyl transferase. J. Biol. Chem. 1989, 264, 17174-17181.
4. Yuasa, H.; Palcic, M.M.; Hindsgaul, O. Synthesis of the carbocyclic analog of uridine 5′-(α-D-galactospyranosyl diphosphate) (UDP-Gal) as an inhibitor of β-(1→4)-galactosyl transferase. Can. J. Chem. 1995, 73, 2190-2195.
5. Schmidt, R.R.; Frische, K. A new galactosyl transferase inhibitor. Bioorg. Med. Chem. Lett. 1993, 3, 1747-1750.
6. Hashimoto, H.; Endo, T.; Kajihara, Y. Synthesis of the first tricomponent bisubstrate analogue that exhibits potent inhibition against GlcNAc:β-1,4-galactosyltransferase. J. Org. Chem. 1997, 62, 1914-1915.
7. Waldscheck, B.; Streiff, M.; Notz, W.; Kinzy, W.; Schmidt, R.R. Galactosyl transferase inhibition based on a new type of disubstrate analogue. Angew. Chem., Int. Ed. Engl. 2001, 40, 4007-4011.
8. Heskamp, B.M.; Veeneman, G.H.; van der Marel, G.A.; van Boeckel, C.A.A.; van Boom, J.H. Synthesis and glycosylating properties of ketopyranosyl donors. Tetrahedron 1995, 51, 5657-5670.
9. Pasquarello, C.; Picasso, S.; Demange, R.; Malissard, M.; Berger, E.G.; Vogel, P.J. The C-disaccharide α-C-(1→3)-mannopyranoside of N-acetylgalactosamine is an inhibitor of glycohydrolases and of human α̃(1→3)-fucosyltransferase VI. Its epimer α-(1→3)- mannopyranoside of N-acetyltalosamine is not. J. Org. Chem. 2000, 65, 4251-4260.
10. Qiao, L.; Murray, B.W.; Shimazaki, M.; Schultz, J.; Wong, C.-H. Synergistic inhibition of human α-1,3-fucosyltransferase V. J. Am. Chem. Soc. 1996, 118, 7653-7662.
11. Jeffries, I.; Bowen, B.R. Synthesis of inhibitors of α-1,3- fucosyltransferase. Bioorg. Med. Chem. Lett. 1997, 7, 1171-1174.
12. Asensio, J.L.; Cañada, F.J.; García-Herrero, A.; Murillo, M.T.; Fernández-Mayoralas, J.B.A.; Kozak, J.; Zhu, Z.; Johnson, C.R.; Jiménez-Barbero, J. Conformational behavior of aza-C-glycosides: experimental demonstration of the relative role of the exo-anomeric effect and 1,3-type interactions in controlling the conformation of regular glycosides. J. Am. Chem. Soc. 1999, 121, 11318-11329.
13. Montero, E.; García-Herrero, J.L.; Asensio, H.K.; Ogawa, S.; Santoyo-González, C.F.J.; Jiménez-Barbero, J. Conformational behaviour of non-hydrolyzable lactose analogues: the thioglycoside, carbaglycoside, and carba-iminoglycoside cases. Eur. J. Org. Chem. 2000, 1945-1952. For reviews on C-glycoside synthesis, see Refs. [14-21].
14. Du, Y.; Linhardt, R.J.; Vlahov, J.R. Recent advances in stereoselective C-glycoside synthesis. Tetrahedron 1998, 54, 9913-9959.
15. Togo, H.; He, W.; Waki, Y.; Yokoyama, M. C-Glycosidation technology with free radical reactions. Synlett 1998, 700-717.
16. Beau, J.-M.; Gallagher, T. Nucleophilic C-glycosyl donors for C-glycoside synthesis. Top. Curr. Chem. 1997, 187, 1-54.
17. Skrydstrup, T.; Vauzeilles, B.; Beau, J.-M. Synthesis of C-oligosaccharides. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G.W., Sinaÿ, P., Eds.; Wiley-VCH: Weinheim, 2000; Vol. 1, 495-530.
18. Beau, J.-M.; Vauzeilles, B. C-glycosyl analogs of oligosaccharides and glycosyl amino acids. In Glycoscience: Chemistry and Chemical Biology; Fraser-Reid, B., Tatsuta, K., Thiem, J., Eds.; Springer: Heidelberg, 2001; Vol. 3, 2679-2724.
19. Postema, M.H.D. C-Glycoside Synthesis; CRC Press: Boca Raton, 1995.
20. Liu, L.; McKee, M.; Postema, M.H.D. Synthesis of C-saccharides. Curr. Org. Chem. 2001, 5, 1133-1167.
21. Levy, D.; Tang, C. The Synthesis of C-Glycosides; Elsevier/Pergamon: Oxford, 1995.
22. Khan, N.; Cheng, X.; Mootoo, D.R. 1-Thio-1,2-O-isopropylidene acetals: novel precursors for the synthesis of complex C-glycosides. J. Am. Chem. Soc. 1999, 121, 4918-4919.
23. Cheng, X.; Khan, N.; Mootoo, D.R. Synthesis of the C-glycoside analogue of a novel sialyl Lewis X mimetic. J. Org. Chem. 2000, 65, 2544-2547.
24. Brill, G.M.; Jackson, M.; Whittern, D.N.; Buko, A.M.; Hill, P.; Chen, R.H.; McAlpine, J.B. Altromycins E, F, G, H and I; additional novel components of the altromycin complex. J. Antibiot. 1994, 47, 1160-1164.
25. Kaskar, B.; Heise, G.L.; Michalak, R.S.; Vishnuvajjala, B.R. Convergent large scale synthesis of protected D-ribonolactone from D-ribose. Synthesis 1990, 1031-1032.
26. Armas, P.D.; Francisco, C.G.; Suarez, E. Reagents with hypervalent iodine: formation of convenient chiral synthetic intermediates by fragmentation of carbohydrate anomeric alkoxy radicals. Angew. Chem., Int. Ed. Engl. 1992, 31, 772-773.
27. Wang, Y.; Babirad, S.A.; Kishi, Y. Preferred conformation of C-glycosides. 8. Synthesis of 1,4-linked carbon disaccharides. J. Org. Chem. 1992, 57, 468-481.
28. Liu, L.; Postema, M.H.D. A unified approach to differentially linked C-disaccharides by ring-closing metathesis. J. Am. Chem. Soc. 2001, 123, 8602-8603.
29. Immel, S.; Fujita, K.; Lichtenthaler, F.W. Solution geometries and lipophilicity patterns of α-cycloaltrin. Chem. Eur. J. 1999, 5, 3185-3192.
30. Dowd, M.K.; French, A.D.; Reilly, P.J. Modeling of aldopyranosyl ring puckering with MM3 (92). Carbohydr. Res. 1994, 264, 1-19.
31. Pine, S.H.; Pettit, R.J.; Geib, G.D.; Cruz, S.G.; Gallego, C.H.; Tijerina, T.; Pine, R.D. Carbonyl methylenation using a titanium-aluminum (Tebbe) complex. J. Org. Chem. 1985, 50, 1212-1218.
32. Pine, S.H.; Shen, G.S.; Hoang, H. Ketone methylenation using the Tebbe and Wittig reagents. A comparison. Synthesis 1991, 165-167.