Semisynthetic ε-(iso)rhodomycin (cas 1401-16-7)s: a new glycosylation variant and modification reactions

Add time:09/02/2019    Source:sciencedirect.com

Synthesis of 7-O-(3-amino-2,3,6-trideoxy-α-l-lyxo-hexopyranosyl)-ε-(iso)rhodomycinones 16 and 17, and their 3′-morpholino derivatives are described. Glycosylation (trimethylsilyl triflate, 10:1 dichloromethane-acetone, −35°) of 1-O-tert-butyldimethylsilyl-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-β-l-lyxo-hexopyranose (4) with ε-rhodomycinone (ε-RMN, 5) or ε-isorhodomycinone (ε-isoRMN, 6) afforded 7-O-α-glycosyl-ε-RMN (9) and -ε-isoRMN (12) in high yield. The glycosyl donors 2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-l-lyxo-hexopyranose (2) or its 1-O-trimethylsilylated α-anomer 3 were less suitable for the glycosylation of these aglycons. Saponification of 9 and 12 provided 16 and 17, respectively, which reacted with various 2,2′-oxydiacetaldehydes under conditions of reductive alkylation to give 3′-morpholinyl-ε-(iso)rhodomycins.

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