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- W2014154753 abstract "The synthesis of the protected ribosylribitol derivatives 15 and 17, which are building blocks for the preparation of fragments of the H. influenzae type b polysaccharide, is presented. Starting from D-ribonolactone (1), 5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol (8) was prepared in seven steps (Scheme 1). Coupling of 8 with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (9) in the presence of trimethylsilyl trifluoromethanesulfonate gave the ribosylribitol derivative 10 (Scheme 2), which was debenzoylated to afford compound 11. The C-3′- and C-5′-hydroxyl functions of the ribose moiety of 11 were protected with the 1,1,3,3-tetraisopropyldisiloxane-1,3-diyl group and the C-2′ position with the benzyloxymethyl group. Compound 13 thus obtained was converted into its 5-O-trans-1-propenyl isomer 14. Cleavage of the propenyl group from 14 gave compound 15, which can be phosphorylated at O-5 of the ribitol. On the other hand, removal of the 3′,5′-protection from 14 and subsequent blocking of the primary hydroxyl function yielded ribosylribitol derivative 17 having a 3′-hydroxyl function available for phosphorylation." @default.
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- W2014154753 date "2010-09-02" @default.
- W2014154753 modified "2023-09-25" @default.
- W2014154753 title "Synthesis of fragments of the capsular polysaccharide of Haemophilus influenzae type b: Part I. Preparation of suitably protected 1-O-β-D-ribofuranosyl-D-ribitol building blocks" @default.
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- W2014154753 doi "https://doi.org/10.1002/recl.19871060905" @default.
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