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  • Title: Design and synthesis of regioselective cleaving reagents for oligonucleotides.
    Author: Mori S, Ohgo Y, Tanaka H, Katoh A, Kaji H, Samejima T, Mitsunobu O.
    Journal: Nucleic Acids Symp Ser; 1993; (29):45-6. PubMed ID: 8247787.
    Abstract:
    Reaction of methyl 2,3-anhydro-alpha-D-ribofuranoside with allylmagnesium chloride selectively took place at the 2-C position to afford methyl 2-C-allyl-2-deoxy-alpha-D-arabinofuranoside. 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose reacted with allylic alcohols in the presence of BF3.OEt2 to give the corresponding allyl beta-D-ribofuranosides. The allyl group in these compounds were converted into a variety of functional groups which include bromoacetoxy, oxylanyl, tosyloxy, and azide.
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