Journal of the Chemical Society. Perkin transactions I p. 733 - 740 (1984)
Update date:2022-08-04
Topics:
Collins, Peter M.
Overend, W. George
Racz, Veronica M.
Sequential treatment of methyl 3,4-O-isopropylidene-β-L-erythro-pentopyranosidulose (1) with aqueous sodium hydroxide and phenylhydrazine results in elimination of acetone and formation of 2S-methoxytetrahydropyran-3,4-dione 4-phenylhydrazone (7) as the main product.Similarly, methyl 6-deoxy-3,4-O-isopropylidene-α-L-lyxo-hexopyranosid-2-ulose (2) was converted into 2R-methoxy-6S-methyltetrahydropyran-3,4-dione 4-phenylhydrazone (8).The effect of base on the related uloside, methyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexapyranoside-4-ulose (16),resulted in the formation of 3-hydroxy-2-methyl-4H-pyran-4-one (maltol) (17).Compounds (7) and (8) have been converted into, respectively, 3-amino-3,4-dideoxy-D-erythro-pentopyranose (22) and 3-amino-3,4,6-trideoxy-L-ribo-hexopyranose (25).
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