Synthesis of 7′-(3-hydroxypropyl)fortimicin A and 6′-epifortimicin A

Add time:07/19/2019    Source:sciencedirect.com

1,10-Di-O-acetyl-2,3,4,6,7,8,9-heptadeoxy-2,6-bis(2,4-dinitrophenylamino)-l-lyxo-decopyranose (7 and -d-ribo-decopyranose (8) have been prepared from methyl 2-acetamido-2,3,4,6-tetradeoxy-6-nitro-α-d-erythro-hexopyranoside via a nitro aldol reaction with 4-[(tetrahydropyranyl)oxy]butanal in the presence of cesium fluoride, and their configurations at C-6 have been established by conversion of the precursor of 8, namely, methyl 2,6-diacetamido-10-O-acetyl-2,3,4,6,7,8,9-heptadeoxy-α-ribo-decopyranoside, into the known methyl 2,6-diacetamido-2,3,4,6,7,8,9,10-octadeoxy-α-d-decopyranoside. The title fortimicin A derivatives, 7′-(3-hydroxypropyl)fortimicin A and 6′-epifortimicin A, have been synthesized by condensation of compound 7 and 8, respectively, with 2,5-di-O-benzoyl-1,4-bis[N-(methoxycarbonyl)]fortamine B, followed by deprotection and introduction of a glycyl group. Their antimicrobial activities have been found to be weak compared to that of fortimicin A.

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