Henry condensations with 4,6-O-benzylidenylated and non-protected D-glucose and L-fucose via DBU-catalysis

Tetrahedron Letters

Volumn 44, Issue 29, 2003, Pages 5495-5498

  Phiasivongsa, Pasit ^a   Samoshin, Vyacheslav V ^a   Gross, Paul H ^a  

^a UNIVERSITY OF THE PACIFIC   (United States)

Author keywords

C glycoside; DBU; Nitromethane

Indexed keywords

ACETAL DERIVATIVE; C GLYCOPYRANOSIDE; CARBOHYDRATE; GLUCOSE; LEVO FUCOSE; NITROMETHANE; PYRANOSE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; BENZYLIDENYLATION; CARBOHYDRATE ANALYSIS; CATALYSIS; CATALYST; CHEMICAL REACTION; HENRY CONDENSATION; KINETICS; MOLECULAR BIOLOGY; PROTECTION; REGULATORY MECHANISM; THERMODYNAMICS;

EID: 0037863073     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01328-5     Document Type: Article

References (16)

1. Flowers H.M. Adv. Carbohydr. Chem. Biochem. 39:1981;279.
2. Bimwala R.M., Vogel P. Helv. Chim. Acta. 72:1989;1825.
3. Hanessian S., Pernet A.G. Adv. Carbohydr. Chem. Biochem. 33:1976;111.
4. Kishi Y. Pure Appl. Chem. 61:1989;313.
5. Levy D.E., Tang C. The Chemistry of C-Glycosides. 1995;4 Pergamon, Elsevier Science Ltd, Oxford, UK.
6. Fritz H., Lehman J., Schlesselman P. Carbohydr. Res. 113:1983;71.
7. Gross P.H. Carbohydr. Poly. 37:1998;215.
8. Sowden J.C., Fischer H.O.L. J. Am. Chem. Soc. 68:1946;1511.
9. Petrus L., Bystricky S., Sticzay T., Bilik V. Chemicke Zvesti. 36:1982;103.
10. Köll P., Petrusova M., Petrus L., Kopf J. Carbohydr. Res. 248:1993;349.
11. Drew K., Gross P.H. Tetrahedron. 47:1991;6113.
12. Wang X., Gross P.H. J. Org. Chem. 60:1995;1201.
13. Swain C.G., Brown J.F. J. Am. Chem. Soc. 74:1952;2538.
14. Li J.B. Aldichim. Acta. 5:1972;5.
15. 2O to give 4b : 0.15 g, 0.39 mmol (2.1%); mp 124-126°C.
16. 2 (268.22): C, 35.82; H, 6.01; N, 10.44. Found; C, 35.27; H, 6.15; N, 10.14.