Synthesis of guanosine 5′-(β-L-fucopyranosyl)-diphosphate revisited

Article abstract of DOI:10.1080/07328309608005678

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).

Full text of DOI:10.1080/07328309608005678

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Journal of Carbohydrate Chemistry
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Synthesis of Guanosine 5′-(β-L-
Fucopyranosyl)-Diphosphate Revisited
B. M. Heskamp a , H. J.G. Broxterman a , G. A. van der Marel a & J.
H. van Boom a
a Leiden Institute of Chemistry Gorlaeus Laboratories Leiden
University , P.O. Box 9502, 2300 RA, Leiden, The Netherlands
Published online: 22 Aug 2006.
To cite this article: B. M. Heskamp , H. J.G. Broxterman , G. A. van der Marel & J. H. van Boom
(1996) Synthesis of Guanosine 5′-(β-L-Fucopyranosyl)-Diphosphate Revisited, Journal of Carbohydrate
Chemistry, 15:5, 611-622, DOI: 10.1080/07328309608005678
To link to this article: http://dx.doi.org/10.1080/07328309608005678
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