Carbohydrate Research p. 63 - 70 (1980)
Update date:2022-08-04
Topics:
Dettinger, Hans-Martin
Lehmann, Jochen
Wallenfels, Kurt
The reaction of ethyl vinyl ether and 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (1) in the presence of Hg(OAc)2 and toluene-p-sulphonic acid as catalysts yielded the acetylated vinyl, 1-ethoxyethyl, and 1-ethoxybut-3-enyl glycosides in varying proportions.Crystalline 1-ethoxybut-3-enyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2), vinyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (3), and 1-ethoxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4) were isolated by chromatography.Compound 4 was also prepared by the reaction of 1 with cold acetaldehyde diethyl acetal containing a trace of acetic acid, and its α anomer (5) by the reaction of 1 with boiling acetaldehyde diethyl acetal containing a trace of acetic acid.Each deacetylated D-glucoside was cleaved by the corresponding D-glucosidase, to yield D-glucose and either acetaldehyde (from deacetylated 3-5) or but-3-enal (from deacetylated 2).
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Doi:10.1016/j.tet.2004.06.061
(2004)Doi:10.1021/ja00297a039
(1985)Doi:10.1002/jps.2600520923
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(1981)Doi:10.1246/cl.1980.1133
(1980)