Acetonation of L-pentoses and 6-deoxy-L-hexoses under kinetic control using heterogeneous acid catalysts.
The fibrous polymer-supported sulfonic acid catalyst Smopex-101 H+ proved to be an efficient catalyst for the preparation of O-isopropylidene derivatives from a series of rare sugars. Acetonation of the reducing sugars L-arabinose, L-ribose, L-xylose, L-fucose, and L-rhamnose in N,N-dimethylformamide by 2,2-dimethoxypropane or 2-methoxypropene led to the formation of the kinetically favored di-O- and/or mono-O-isopropylidene derivatives in 46-88% yields. The method consists of a simple experimental procedure which does not require predried solvents or reagents. The catalyst is easily recovered and can be regenerated making the procedure economically viable even for large-scale synthesis.
Laboratory of Organic Chemistry, Abo Akademi University, Abo, Finland.
Jonas J
JJ
Forsman
Reko
R
Leino
D000096:Acetone / Q000737:chemistry*; D002384:Catalysis; D006601:Hexoses / Q000737:chemistry*; D007700:Kinetics; D008738:Methyl Ethers / Q000737:chemistry; D010429:Pentoses / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry; D013451:Sulfonic Acids / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry
D006601:Hexoses; D008738:Methyl Ethers; D010429:Pentoses; D020005:Propanols; D013451:Sulfonic Acids; D014753:Vinyl Compounds; D000096:Acetone; C534882:2-methoxypropene; C017240:2,2-dimethoxypropane