Studies on enolization of aldehydo-aldose derivatives.
Acetylation of the 2,3-O-isopropylidene derivative (1) of D-glyceraldehyde with hot acetic anhydride in the presence of sodium acetate give a mixture of (Z)- and (E)-enol acetates (2 and 3), together with the acetylated racemic aldehydrol (4) of 1. Likewise, the acyclic aldehydo 2,3:4,5-diisopropylidene acetals of D- and L-arabinose, D-xylose, and D-ribose underwent conversion into enol acetates, with the (Z) isomers preponderating, and convertible photochemically into the corresponding (E) isomers. Under other conditions of acetylation, the aldehydo derivatives were converted into the corresponding aldehydrol diacetates.
Eitelman
Stephen J
SJ
Department of Chemistry, American University, Washington, DC 20016, USA.
Horton
Derek
D
D000107:Acetylation; D000447:Aldehydes / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D009005:Monosaccharides / Q000737:chemistry*; D010429:Pentoses / Q000737:chemistry; D010777:Photochemistry
D000447:Aldehydes; D009005:Monosaccharides; D010429:Pentoses