Synthesis of a Pseudodisaccharide Suitable for Synthesis of Ring I Modified 4,5-2-Deoxystreptamine Type Aminoglycoside Antibiotics | Zendy

Amr Sonousi | Zendy; Andrea Vasella | Zendy; David Crich | Zendy

Open Access

Synthesis of a Pseudodisaccharide Suitable for Synthesis of Ring I Modified 4,5-2-Deoxystreptamine Type Aminoglycoside Antibiotics

Author(s) -

Amr Sonousi,

Andrea Vasella,

David Crich

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.0c00743

Subject(s) - paromomycin , chemistry , aminoglycoside , neomycin , stereochemistry , ring (chemistry) , cleavage (geology) , glycosyl , aminocyclitol , combinatorial chemistry , antibiotics , organic chemistry , biochemistry , fracture (geology) , geotechnical engineering , engineering

To facilitate the synthesis of paromomycin and/or neomycin analogues, we describe a cleavage of ring I from paromomycin that proceeds in the presence of azides and affords a glycosyl acceptor for the installation of a modified ring I. A paromomycin 4',6'-diol is oxidized by the Dess-Martin periodinane followed by m -chloroperoxybenzoic acid. Base treatment then affords a protected pseudodisaccharide, which functions as a glycosyl acceptor. The method should also apply to the cleavage of pyranosyl 4,6-diols from oligosaccharides and glycoconjugates.

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