Author:
Aspinall G. O.,Barron P. E.
Abstract
The action of various bases on the three hexuronic esters, methyl (methyl 2,3,4-tri-O-methyl-β-D-glucopyranosid)uronate (12), methyl (methyl 4-O-methanesulfonyl-2,3-di-O-methyl-β-D-glucopyranosid)uronate (13), and methyl (methyl 4-O-acetyl-2,3-di-O-methyl-β-D-glucopyranosid)uronate (14), leading to elimination of the 4-O-substituents and formation of methyl (methyl 4-deoxy-2,3-di-O-methyl-α-L-threo-hex-4-enopyranosid)uronate (15) has been studied. It is concluded that effectiveness of 4-O-substituents as leaving groups is in the sequence, methanesulfonyloxy > acetoxy > methoxy.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
35 articles.
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