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Volumn 67, Issue 20, 2002, Pages 6960-6970

A general strategy for the practical synthesis of nojirimycin C-glycosides and analogues. Extension to the first reported example of an iminosugar 1-phosphonate

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDIC FUNCTIONS;

EID: 0037019953     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0203903     Document Type: Article
Times cited : (67)

References (87)
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    • Glycosyl transfer
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    • note
    • It is noteworthy that L-sorbose has been used as the starting material for the first synthesis, as well as for some of the shortest syntheses, of 1-deoxynojirimycin, but not for the preparation of chain-extended analogues (see ref 1b).
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    • In our hands, compound 6 could be obtained in one step from L-sorbose in 80% yield; see: Paulsen, H.; Sangster, I.; Heyns, K. Chem. Ber. 1967, 100, 802.
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    • note
    • Diol 16c with the vinyl group at C1 was found to decompose after a few days of storage at -20°C. To avoid this degradation, 16c was directly acetylated after the reductive amination reaction.
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    • Reference 5b
    • For examples of iminosugar C-glycoside analogues of glycosyl 1-phosphate, see: (a) Reference 5b. (b) Bosco, M.; Bisseret, P.; Bouix-Peter, C.; Eustache, J. Tetrahedron Lett. 2001, 42, 7949. (c) Schuster, M.; He, W.-F.; Blechert, S. Tetrahedron Lett. 2001, 42, 2289. (d) Gautier-Lefebvre, I.; Behr, J.-B.; Guillerm, G.; Ryder, N. S. Bioorg. Med. Chem. Lett. 2000, 10, 1483. (e) Kajimoto, T.; Chen, L.; Liu, K. K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678.
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    • For examples of iminosugar C-glycoside analogues of glycosyl 1-phosphate, see: (a) Reference 5b. (b) Bosco, M.; Bisseret, P.; Bouix-Peter, C.; Eustache, J. Tetrahedron Lett. 2001, 42, 7949. (c) Schuster, M.; He, W.-F.; Blechert, S. Tetrahedron Lett. 2001, 42, 2289. (d) Gautier-Lefebvre, I.; Behr, J.-B.; Guillerm, G.; Ryder, N. S. Bioorg. Med. Chem. Lett. 2000, 10, 1483. (e) Kajimoto, T.; Chen, L.; Liu, K. K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678.
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    • For examples of iminosugar C-glycoside analogues of glycosyl 1-phosphate, see: (a) Reference 5b. (b) Bosco, M.; Bisseret, P.; Bouix-Peter, C.; Eustache, J. Tetrahedron Lett. 2001, 42, 7949. (c) Schuster, M.; He, W.-F.; Blechert, S. Tetrahedron Lett. 2001, 42, 2289. (d) Gautier-Lefebvre, I.; Behr, J.-B.; Guillerm, G.; Ryder, N. S. Bioorg. Med. Chem. Lett. 2000, 10, 1483. (e) Kajimoto, T.; Chen, L.; Liu, K. K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678.
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    • Very recently, Schmidt et al. observed that the presence of UDP on the β-side of the sugar donor moiety of a bisubstrate analogue led to higher inhibition of a retaining glycosyltransferase (galactosyltransferase LgtC from Neisseria meningitidis) than when UDP was on the α-side as in the natural sugar nucleotide donor: Waldscheck, B.; Streiff, M.; Notz, W.; Kinzy, W.; Schmidt, R. R. Angew. Chem., Int. Ed. 2001, 40, 4007.
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