Reactions of D-lyxose and D-xylose with 2-methoxypropene under kinetic conditions

Article abstract of DOI:10.1016/0008-6215(91)89046-I

D-Lyxose (1) undergoes acetonation under kinetic conditions with 2-methoxypropene to give 2,3-O-isopropylidene-α-D-lyxofuranose (2) in high yield, further characterized as its 1,5-diacetate 3, thus affording a preparative route to 2.Forcing conditions are required to bring D-xylose (5) into reaction, leading to 39percent of 3,5-O-isopropylidene-α,β-D-xylofuranose (7, further characterized as its 1,2-diacetate 9), 33percent of 1,2:3,5-di-O-isopropylidene-α-D-xylofuranose (6), and 20percent of 2,3:4,5-di-O-isopropylidene-aldehydo-D-xylose (8, further characterized as its aldehydrol diacetate 10).The results are all readily rationalized within the framework of the general principles earlier advanced for kinetic acetonation of sugars.