Synthesis of Guanosine 5′-(β-L-Fucopyranosyl)-Diphosphate Revisited
- 1 July 1996
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 15 (5) , 611-622
- https://doi.org/10.1080/07328309608005678
Abstract
It will be demonstrated that a successful synthesis of β-L-fucopyranose-1-phosphate (2), a key intermediate in the preparation of guanosine 5′-(β-L-fucopyranose)-diphosphate (1), strongly depends on the nature of the acyl protecting groups for the non-anomeric hydroxyl functions. Thus, the perbenzoylated, instead of peracetylated, α-L-fucopyranosyl trichloroacetimidate (11) or the corresponding ethyl β-thiofucopyranoside proved to be a convenient starting compound for the preparation of 2. Further, condensation of N,N′-dicyclohexyl-4-morpholinecarboxamidinium guanosine 5′-morpholidophosphate with excess 2 gave the title compound without concomitant formation of bisguanosine-5′-diphosphate (16).Keywords
This publication has 24 references indexed in Scilit:
- Solution- and Solid-Phase Synthesis of Inhibitors of H. pylori Attachment and E-Selectin-Mediated Leukocyte AdhesionJournal of the American Chemical Society, 1994
- The Sialyl Lewisx Group and its Analogues as Ligands for Selectins: Chemoenzymatic Syntheses and Biological FunctionsAngewandte Chemie International Edition in English, 1994
- Chapter 22. Cell Adhesion and CarbohydratesPublished by Elsevier ,1994
- Use of human-milk fucosyltransferase in the chemoenzymic synthesis of analogues of the sialyl Lewis and sialyl Lewis tetrasaccharides modified at the C-2 position of the reducing unitCarbohydrate Research, 1993
- Conversion of GalNAcβ(1–4)GlcNAcβ‐OMe into GalNAcβ(1–4)‐[Fucα(1–3)]GlcNAcβ‐OMe using human milk α3/4‐fucosyltransferase synthesis of a novel terminal element in glycoprotein glycansFEBS Letters, 1993
- Efficient enzymatic synthesis of the sialyl‐LewisX tetrasaccharideFEBS Letters, 1993
- Nucleoside phosphate sugars: syntheses on practical scales for use as reagents in the enzymatic preparation of oligosaccharides and glycoconjugatesAccounts of Chemical Research, 1992
- Synthesis and structural analysis using 2-D NMR of sialyl Lewis X (SLex) and Lewis X (Lex) oligosaccharides: ligands related to E-selectin [ELAM-1] binding.Journal of the American Chemical Society, 1992
- Synthesis of novel disaccharides based on glycosyltransferases: β1,4galactosyltransferaseTetrahedron Letters, 1991
- Synthesis of cluster sialoside inhibitors for influenza virusJournal of the American Chemical Society, 1991