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Synlett 1996; 1996(4): 313-314
DOI: 10.1055/s-1996-5401
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Synthesis of 2’-O-[(4’’-O-sorboyl)-α-L-fucopyranosyl]inosine: A Shimofuridin analogue

Howard I. Duynstee, Eric R. Wijsman, Gijs A. van der Marel, Jacques H. van Boom*
  • *Leiden Institute of Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands
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Publication Date:
31 December 2000 (online)

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Trimethylsilyl triflate mediated glycosylation of 3’,5’-O-(tetraisopropyldisiloxane-1,3-diyl)-1-N-pivaloyloxymethylinosine (4) with dibutyl 4-O-acetyl-2,3-di-O-benzyl-α/β-L-fucopyranosyl phosphate (6) gave nucleoside 7, which was transformed in three steps into acetonide 10. Acylation of 10 with sorbic acid followed by deprotection gave the title compound.

α-fucosylation - protecting group strategy - sorboylation