63 2,4-ジアミノ糖誘導体の合成研究

概要

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In order to examine the relationship between the configuration of the 2,4-diaminosugar of kasugamycin or prumycin and their activities, facile syntheses of aminosugars and a few diastereomers or homologues were explored. It was found that 3,6-dideoxy-D-hexosides are easily converted into the corresponding 2,4-diamino derivatives via simultaneous substitution of 2,4-dl-O-mesyl groups with sodium azide in HMPA. Thus, benzyl β-kasugaminide 9 was obtained from D-glucose in ca, 20% total yield via the corresponding abequoside 7. Prumycin 23 was synthesized by eight-step conversion of D-xylose in a good yield, via the azidolysis of 4-(N-benzyloxycar-bonyl-D-alanyl)amido-4-deoxy-2,3-epoxy-β-L-ribopyranoside 29a in which the bulkyness of 4-substituent play an important roll for the stereoselectivity in the ring opening.
天然有機化合物討論会の論文
1975-10-01