Urea glycoside synthesis in water

Synlett

Volumn , Issue 6, 2004, Pages 1019-1022

  Ichikawa, Yoshiyasu ^a   Matsukawa, Yohei ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Carbohydrates; Glycosides; Glycosylations

Indexed keywords

CARBAMIC ACID DERIVATIVE; GLUCOSYL CARBAMATE; GLYCOSIDE; OLIGOSACCHARIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; COLUMN CHROMATOGRAPHY; CONJUGATE;

EID: 3142691003     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822902     Document Type: Article

References (23)

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14. Steyermark, P. R. J. Org. Chem. 1962, 27, 1058.
15. 2O, NaOAc, refluxed for 1 h) gave N-acetate iii (Scheme 7). See the reference: Kovacs, J.; Pinter, I. Carbohydr. Res. 1991, 210, 155.
16. For the reactivity of strained carbamates, see the reference: Hall, H. K. Jr.; El-Shekeil, A. J. Org. Chem. 1980, 45, 5325.
17. (a) Pinter, I.; Kovacs, J.; Toth, G. Carbohydr. Res. 1995, 273, 99.
18. (b) Analogous O-unprotected glucosyl thiocarbamate and its reaction with amines in water has been reproted. See the reference: Maya, I.; López, ; Fernández-Bolaños, J. G.; Robina, I.; Fuentes, J. Tetrahedron Lett. 2001, 42, 5413.
19. (c) López, Ó.; Maya, I.; Fuentes, J.; Fernández- Bolaños, J. G. Tetrahedron 2004, 60, 61.
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21. The separation of glucose, hydrolyzed product of 1, by ODS column was difficult in this case.
22. Nishiyama, T.; Ichikawa, Y.; Isobe, M. Synlett 2004, 89; and references therein.
23. For recent examples of the pseudooligosaccharides with thiourea linkage, see: Jiméne Blanco, J. L.; Bootello, P.; Ortiz Mellet, C.; Gutiérrez Gallego, R.; García Fernández, J. M. Chem. Commun. 2004, 92.