D-Arbinose-Based Synthesis of homo-C-d4T and homo-C-thymidine

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Bogdan Doboszewski

2009

Scholarcy highlights

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  • The α,β-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-β- and -α-D-arabinofuranoses, separable after isopropylidenation step. 2,5-Anhydro-1,3-O-isopropylidene-D-glucitol was converted into 2,5-anhydro-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol and 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine
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