Chemical and Pharmaceutical Bulletin p. 90 - 96 (1993)
Update date:2022-08-05
Topics:
Saito
Sumita
Ichinose
Kanda
When acetylated pyranose-1,2-(ethyl orthoacetates) were hydrolyzed in acidic solvents, the ring-opening of the orthoacetate rings was influenced by the axial or equatorial OAc group at C-4 on the pyranoses; on acid-catalyzed hydrolysis, 3,4,6-tri-O-acetyl-α-D-galactopyranose- (8) and methyl 3,4-di-O-acetyl-α-D-galacturonatopyranose-1,2-(ethyl orthoacetate) (16) having an axial OAc group at C-4 on the pyranose rings gave 1,3,4,6-tetra-O-acetyl-α-D-galactopyranose (9) and methyl 1,3,4-tri-O-acetyl-α-D-galacturonatopyranose (23), respectively, whereas 3,4,6-tri-O-acetyl-α-D-glucopyranose- (10) and methyl 3,4-di-O-acetyl-α-D-glucuronatopyranose-1,2-(ethyl orthoacetate) (22) having an equatorial OAc group at C-4 on the pyranose rings gave 2,3,4,6-tetra-O-acetyl-D-glucopyranose (11) and methyl 2,3,4-tri-O-acetyl-D-glucuronatopyranose (24), respectively. On the acid-catalyzed hydrolysis, 3,4-di-O-acetylβ-L-arabinopyranose-1,2-(ethyl orthoacetate) (34) having an axial OAc group at C-4 on the pyranose ring gave a mixture of 1,3,4-tri-O-acetyl-β-L- (35) and 2,3,4-tri-O-acetyl-L-arabinopyranose (36). These selectivities of ring-opening of the 1,2-(orthoacetates) were considered to have resulted from the differences of the conformers of the 1,2-(orthoacids) intermediates derived from the 1,2-(orthoacetates) and the orientation of the acetyl groups at C-4 on the pyranose rings.
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Doi:10.1039/dt9960004227
(1996)Doi:10.1016/S0040-4039(96)02151-X
(1996)Doi:10.1016/S0040-4039(96)02101-6
(1996)Doi:10.1021/ol402815d
(2013)Doi:10.1016/j.ica.2019.05.032
(2019)Doi:10.1016/S0040-4039(00)71385-2
(1980)