Reaction sof d-lyxose and d-xylose with 2-Methoxypropene (cas 116-11-0) under kinetic conditions☆

Add time:08/24/2019    Source:sciencedirect.com

d-Lyxose (1) undergoes acetonation under kinetic conditions with 2-Methoxypropene (cas 116-11-0) 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 39% of 3,5-O-isopropylidene-α-β-d-xylofuranose (7, further characterized as its 1,2-diacetate 9), 33% of 1,2:3,5-di-O-isopropylidene-α-d-xylofuranose (6), and 20% 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.

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