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A new method for the 3′-deoxygenation of butirosins A and B by Hiroshi Fukase; Nariakira Mizokami; Satoshi Horii is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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An aziridine ring-formation involving the reaction of adjacent amino and alcohol groups with triphenylphosphine, carbon tetrachloride, and triethylamine was applied at the 2' and 3' positions of butirosin A (la) and B (lb). The amino groups at the 2' position of la and lb were p-methoxybenzylated to increase the nucleophilicity of the nitrogen atom and to avoid the formation of a P-N linkage, and the N-p-methoxybenzyl derivatives were converted into the aziridine derivatives, which were then subjected to hydrogenolysis and removal of the protecting groups to give Y-deoxybutirosin A (Ta) and B (7b), respectively. This new method is compared with the conventional N,O-protecting method that involves several complex steps.

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Author

Hiroshi Fukase; Nariakira Mizokami; Satoshi Horii

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1978

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)