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Volumn 57, Issue 20, 2001, Pages 4283-4295

An efficient synthesis of new 1′-C-methyl-α-O-disaccharides using 1-methylenesugars as the glycosyl donors

Author keywords

1 C methyl disaccharides; 1 methylenesugars; Neighboring group participation; O glycosidation; Sugar lactones

Indexed keywords

2,3,4,6 TETRA O BENZYL 1 METHYLENESUGAR DERIVATIVE; CARBOHYDRATE DERIVATIVE; DISACCHARIDE; METHYL O (1' C METHYL 2',3',4',6' TETRA O ACETYL ALPHA DEXTRO GALACTOPYRANOSYL) (1'-6) 2,3,4 TRI O ACETYL ALPHA DEXTRO GLUCOSIDE; METHYL O (1' C METHYL 2',3',4',6' TETRA O ACETYL ALPHA DEXTRO GLUCOPYRANOSYL) (1'-6) 2,3,4 TRI O ACETYL ALPHA DEXTRO GLUCOSIDE; METHYL O (1' C METHYL 2',3',4',6' TETRA O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL) (1'-4) 2,3,6 TRI O BENZYL ALPHA DEXTRO GLUCOSIDE; METHYL O (1' C METHYL 2',3',4',6' TETRA O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL) (1'-6) 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOSIDE; METHYL O (1' C METHYL 2',3',4',6' TETRA O BENZYL ALPHA DEXTRO GLUCOPYRANOSYL) (1'-4) 2,3,6 TRI O BENZYL ALPHA DEXTRO GLUCOSIDE; METHYL O (1' C METHYL 2',3',4',6' TETRA O BENZYL ALPHA DEXTRO GLUCOPYRANOSYL) (1'-6) 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOSIDE; METHYL O (1' C METHYL 2',3',4',6' TETRA O BENZYL ALPHA DEXTRO MANNOPYRANOSYL) (1'-4) 2,3,6 TRI O BENZYL ALPHA DEXTRO GLUCOSIDE; METHYL O (1' C METHYL 2',3',4',6' TETRA O BENZYL ALPHA DEXTRO MANNOPYRANOSYL) (1'-6) 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOSIDE; METHYL O (1' C METHYL ALPHA DEXTRO GALACTOPYRANOSYL) (1'-) ALPHA DEXTRO GLUCOSIDE; METHYL O (1' C METHYL ALPHA DEXTRO GLUCOPYRANOSYL) (1'-4) ALPHA DEXTRO GLUCOSIDE; METHYL O (1' C METHYL ALPHA DEXTRO GLUCOPYRANOSYL) (1'-6) ALPHA DEXTRO GLUCOSIDE; METHYL O (1' C METHYL ALPHA DEXTRO MANNOPYRANOSYL) (1'-4) ALPHA DEXTRO GLUCOSIDE; METHYL O (1' C METHYL ALPHA DEXTRO MANNOPYRANOSYL) (1'-6) ALPHA DEXTRO GLUCOSIDE; UNCLASSIFIED DRUG;

EID: 0035858616     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)00319-2     Document Type: Article
Times cited : (40)

References (40)
  • 1
    • 0001094662 scopus 로고    scopus 로고
    • For reviews see: (a)
    • For reviews see: (a) Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
    • (1996) Chem. Rev. , vol.96 , pp. 683-720
    • Dwek, R.A.1
  • 4
    • 0001367771 scopus 로고    scopus 로고
    • For recent reviews see: (a)
    • For recent reviews see: (a) Ganem, B. Acc. Chem. Res. 1996, 29, 340-347.
    • (1996) Acc. Chem. Res. , vol.29 , pp. 340-347
    • Ganem, B.1
  • 12
    • 0003713167 scopus 로고    scopus 로고
    • Also see articles in: (i) (Ed.) Blackie Academic and Professional, London
    • Also see articles in: (i) Boons, G.-J. (Ed.). Carbohydrate Chemistry; Blackie Academic and Professional, London, 1998.
    • (1998) Carbohydrate Chemistry
    • Boons, G.-J.1
  • 25
    • 0020477042 scopus 로고
    • To the best of our knowledge, there were only two papers on the O-glycosylations using 1-methylenesugar as the glycosyl donor. (a) the reaction promoted by iodonium ion, see: Ref. 8. (b) enzymatic reaction, see
    • To the best of our knowledge, there were only two papers on the O-glycosylations using 1-methylenesugar as the glycosyl donor. (a) the reaction promoted by iodonium ion, see: Ref. 8. (b) enzymatic reaction, see: Schlesselmann, P.; Fritz, H.; Lehmann, J.; Uchiyama, T.; Brewer, C. F.; Hehre, E. J. Biochemistry 1982, 21, 6606-6614.
    • (1982) Biochemistry , vol.21 , pp. 6606-6614
    • Schlesselmann, P.1    Fritz, H.2    Lehmann, J.3    Uchiyama, T.4    Brewer, C.F.5    Hehre, E.J.6
  • 26
    • 0014115844 scopus 로고
    • Prepared from the corresponding 2,3,4,6-tetra-O-benzylhexopyranose by the oxidation with acetic anhydride and DMSO. see
    • Prepared from the corresponding 2,3,4,6-tetra-O-benzylhexopyranose by the oxidation with acetic anhydride and DMSO. see: Kuzuhara, H.; Fletcher Jr., H. G. J. Org. Chem. 1967, 32, 2531-2534.
    • (1967) J. Org. Chem. , vol.32 , pp. 2531-2534
    • Kuzuhara, H.1    Fletcher H.G., Jr.2
  • 29
    • 0002106231 scopus 로고
    • Compound 4 was prepared by the modified method of Garegg's. see
    • Compound 4 was prepared by the modified method of Garegg's. see: Garegg, P.; Hultberg, H. Carbohydr. Res. 1981, 93, C10-C11.
    • (1981) Carbohydr. Res. , vol.93
    • Garegg, P.1    Hultberg, H.2
  • 30
    • 0028889724 scopus 로고
    • In Carbon-proton Coupling Constants in the Conformational Analysis of Sugar Molecules
    • Horton, D.; Ed. Academic Press, San Diego
    • Tvaroska, I.; Travel, F. R. In Carbon-proton Coupling Constants in the Conformational Analysis of Sugar Molecules; Horton, D.; Ed. Adv. Carbohydr. Chem. Biochem., Academic Press, San Diego, 1995, Vol. 51, pp. 15-61.
    • (1995) Adv. Carbohydr. Chem. Biochem. , vol.51 , pp. 15-61
    • Tvaroska, I.1    Travel, F.R.2
  • 33
    • 0002204363 scopus 로고    scopus 로고
    • Chemical Synthesis of O-glycosides
    • G.-J. Boons. London: Blackie Academic and Professional
    • Veeneman G.H. Chemical Synthesis of O-glycosides. Boons G.-J. Carbohydare Chemistry. 1998;99-174 Blackie Academic and Professional, London.
    • (1998) Carbohydare Chemistry , pp. 99-174
    • Veeneman, G.H.1
  • 38
    • 0024930829 scopus 로고
    • In Anomeric and Exo-anomeric Effects in Carbohydrate Chemistry
    • (a) Tipson, R. S.; Horton, D.; Eds. Academic Press, San Diego
    • (a) Tvaroska, I.; Bleha, T. In Anomeric and Exo-anomeric Effects in Carbohydrate Chemistry; Tipson, R. S.; Horton, D.; Eds. Adv. Carbohydr. Chem. Biochem., Academic Press, San Diego, 1989; Vol. 47, pp. 45-123.
    • (1989) Adv. Carbohydr. Chem. Biochem. , vol.47 , pp. 45-123
    • Tvaroska, I.1    Bleha, T.2
  • 39
    • 0343699009 scopus 로고
    • In Anomeric Effect, Origin and Consequences
    • (b) Szarek, W. A.; Horton, D.; Eds. Washington, DC
    • (b) In Anomeric Effect, Origin and Consequences; Szarek, W. A.; Horton, D.; Eds., ACS Symposium. Ser. 87, Am. Chem. Soc., Washington, DC, 1979.
    • (1979) ACS Symposium. Ser. 87, Am. Chem. Soc.
  • 40
    • 0008577168 scopus 로고    scopus 로고
    • Mono- And Oligosaccharides: Structure, Configuration and Conformation
    • G.-J. Boons. London: Blackie Academic and Professional
    • Boons G.-J. Mono- and Oligosaccharides: Structure, Configuration and Conformation. Boons G.-J. Carbohydrate Chemistry. 1998;1-20 Blackie Academic and Professional, London.
    • (1998) Carbohydrate Chemistry , pp. 1-20
    • Boons, G.-J.1


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