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- W1992620566 abstract "Cyclization of D′-methoxy-diglycolaldehyde, prepared by periodate cleavage of methyl β-L-arabinopyranoside, with ethyl nitroacetate gave a mixture of stereoisomers of cyclic α-nitro ester, i.e. methyl (+)-3-deoxy-3-C-ethoxycarbonyl-3-nitropentopyranoside. Catalytic reduction of the cyclic α-nitro ester afforded an isomeric mixture of cyclic α-amino esters, from which, on column chromatography, there could be isolated four diastereoisomers of methyl (+)-3-amino-3-deoxy-3-C-ethoxycarbonylpentopyranoside. Hydrolysis of each diastereoisomer gave the corresponding cyclic (+)-α-amino acid having a skeleton of pentopyranoside. The stereochemistry of the isomeric amino acids was studied by NMR spectroscopy and chemical degradation. On the other hand, three enantiomeric cyclic (−)-α-amino acids were also obtained from methyl β-D-xylopyranoside by the analogous route as that from methyl β-L-arabinopyranoside." @default.
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- W1992620566 date "1969-06-01" @default.
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- W1992620566 title "The Synthesis of Cyclic α-Amino Acids. III. The Synthesis of Methyl (+)- and (−)-3-Amino-3-C-carboxy-3-deoxypentopyranosides" @default.
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- W1992620566 doi "https://doi.org/10.1246/bcsj.42.1719" @default.
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