Acetonation of D-ribose

J. Gelas and D. Horton, Acetonation of D-ribose and D-arabinose with alkyl isopropenyl ethers, Carbohydr. Res. 45 181 (197S). 

Acetonation of D-ribose and D-arabinose using ethyl (or methyl) isopropenyl ether in DMF containing a trace of toluene-p-sulphonic acid has been reported. D-Ribose yielded principally 3,4-O-isopropylidene-jS-D-ribopyranose, together with other minor products such as 2,3-O-isopropylidene-D-ribofuranose, and D-arabinose gave mostly 3,4-0-isopropylidene-)3-D-arabinopyranose and some l,2 3,4-diacetal. D-Fucose and 6-0-methyl-D-galactose afforded 3,4-0-isopro-pylidene derivatives, in 40—60% yield, on treatment with acetone and anhydrous cupric sulphate. D-Ribose also yielded a 3,4-0-isopropylidene derivative (15—20%) on similar treatment, whereas 4,6-0-isopropylidene-D-glucose was obtained in low yield when D-glucose reacted in the presence of DMF. 

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See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

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