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  • Title: Synthesis of methyl 2-O-allyl-(and 3-O-allyl)-5-O-benzyl-beta-D- ribofuranoside.
    Author: Desai T, Gigg J, Gigg R.
    Journal: Carbohydr Res; 1996 Jan 11; 280(2):209-21. PubMed ID: 8593636.
    Abstract:
    D-Ribose was converted into methyl 5-O-benzyl-beta-D-ribofuranoside and this, on tin-mediated allylation, gave a mixture of the 2-O-allyl and 3-O-allyl derivatives which were separated by chromatography. The more polar isomer was characterised as the 3-O-allyl derivative after conversion via 3-O-allyl-5-O-benzyl-1,2-O-isopropylidene-alpha-D-ribofuranose (which was also synthesised from 3-O-allyl-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose) into the known 5-O-benzyl-1,2-O-isopropylidene-alpha-D-ribofuranose. Methyl 3-O-allyl-5-O-benzyl-beta-D-ribofuranoside was converted into methyl 2-O-allyl-5-O-benzyl-beta-D-ribofuranoside via methyl 2-O-allyl-5-O-benzyl-3-O-(prop-1-enyl)-beta-D-ribofuranoside.
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