Synthesis of methyl 2-O-allyl-(and 3-O-allyl)-5-O-benzyl-beta-D- ribofuranoside.
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.
Desai
T
T
Division of Lipid and General Chemistry, National Institute for Medical Research, London, UK.
Gigg
J
J
Gigg
R
R
D002240:Carbohydrate Sequence; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D012266:Ribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
C098448:methyl 2-O-allyl-5-O-benzylribofuranoside; C098449:methyl 3-O-allyl-5-O-benzylribofuranoside; D012266:Ribose