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- W1990302008 abstract "Catalytic hydrogenation of 2,3,4,6-tetra-O-benzyl-1-O-[1-benzyl N-(benzyloxycarbonyl)-l-aspart-4-oyl]-α-glucopyranose (α) in acetic acid-2-methoxyethanol gave 1-O-(l-β-aspartyl)-α-d-glucopyranose (2α) contaminated with 2-O-(l-α-aspartyl)-d-glucopyranose (8). Evidence that 8 was formed from the 1-oyl isomer of 1α, namely 2,3,4,6-tetra-O-benzyl-1-O-[4-benzyl N-(benzyloxycarbonyl)-l-aspart-1-oyl]-α-d-glucopyranose (7α), via 1→2 acyl migration, was obtained by submitting the deprotected d-glucosyl ester to successive N-acetylation, esterification, and O-acetylation; the final product was identified as a 4̃:1 mixture of 2,3,4,6-tetra-O-acetyl-1-O-[1-methyl N-(acetyl)-l-aspart-4-oyl]-α-d-glucopyranose (4α) and 1,3,4,6-tetra-O-acetyl-2-O-[4-methyl N-(acetyl)-l-aspart-1-oyl]-d-glucopyranose (6) which were also prepared by definitive methods. On the other hand, deprotection of 1β gave isomerically pure 2β which was converted into the peracetylated ester derivative 4β; an explanation for the differences in aglycon isomeric purity of 2α and 2β is given. Hydrogenolysis of 7β under the above conditions led to intermolecular transesterification with scission of the C-1 ester bond to give 1-(2-methoxyethyl) l-aspartic acid and d-glucose. Catalytic hydrogenation of 7α and 7β, performed in the presence of trifluoroacetic acid, afforded 1-O-(l-α-aspartyl)-α- and -β-d-glucopyranoside trifluoroacetate salts (α and 11β), respectively. The structure of 11β was established by successive conversion into 2,3,4,6-tetra-O-acetyl-1-O-[4-methyl N-(acetyl)-l-aspart-1-oyl]-β-d-glucopyranose (5β) which was also prepared by definitive methods. Analogous treatment of 11α gave the N-acetyl derivative 12 which underwent 1→2 acyl migration during esterification with diazomethane to give the N-acetyl methyl ester derivative 10; acetylation of 10 afforded 6." @default.
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- W1990302008 date "1976-03-01" @default.
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- W1990302008 title "Syntheses and rearrangements of d-glucosyl esters of aspartic acid linked through the 1- or 4-carboxyl group" @default.
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- W1990302008 doi "https://doi.org/10.1016/s0008-6215(00)83546-6" @default.
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