Chiral phosphoric acid-catalyzed desymmetrizative glycosylation of 2-deoxystreptamine and its application to aminoglycoside synthesisElectronic supplementary information (ESI) available: Experimental procedures and 1H and 13C NMR spectra for compounds 1-9. See DOI: 10.1039/c7cc05052f

This work describes chiral phosphoric acid (CPA)-catalyzed desymmetrizative glycosylation of meso -diol derived from 2-deoxystreptamine. The chirality of CPA dictates the outcome of the glycosylation reactions, and the use of enantiomeric CPAs results in either C4-glycosylated (67 : 33 d.r.) or C6-g...

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Main Authors: Lee, Jeonghyo, Borovika, Alina, Khomutnyk, Yaroslav, Nagorny, Pavel
Format: Article
Language:English
Online Access:Get full text
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Summary:This work describes chiral phosphoric acid (CPA)-catalyzed desymmetrizative glycosylation of meso -diol derived from 2-deoxystreptamine. The chirality of CPA dictates the outcome of the glycosylation reactions, and the use of enantiomeric CPAs results in either C4-glycosylated (67 : 33 d.r.) or C6-glycosylated (86 : 14 d.r.) 2-deoxystreptamines. These glycosylated products can be converted to aminoglycosides, and the application of this strategy to the synthesis of protected iso-neamine and iso-kanamycin B with inverted connection at the C4 and C6 positions is described. This work describes chiral phosphoric acid (CPA)-catalyzed desymmetrizative glycosylation of meso -diol derived from 2-deoxystreptamine.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc05052f