Synthesis of Guanosine 5′-(β-L-Fucopyranosyl)-Diphosphate Revisited
作者:
B.M. Heskamp,
H.J.G. Broxterman,
G.A. van der Marel,
J.H. van Boom,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1996)
卷期:
Volume 15,
issue 5
页码: 611-622
ISSN:0732-8303
年代: 1996
DOI:10.1080/07328309608005678
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
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 of2. Further, condensation ofN,N′-dicyclohexyl-4-morpholinecarboxamidinium guanosine 5′-morpholidophosphate with excess2gave the title compound without concomitant formation of bisguanosine-5′-diphosphate (16).
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