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Sulfamate-Tethered Aza-Wacker Cyclization Strategy for the Syntheses of 2-Amino-2-deoxyhexoses: Preparation of Orthogonally Protected d-Galactosamines

Paul, Debobrata
Mague, Joel T.
Sathyamoorthi, Shyam
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Abstract
We present a new strategy for the assembly of protected d-galactosamine synthons. Our route uses a sulfamate-tethered aza-Wacker cyclization as a key step and commences from d-erythrono-1,4-lactone. This stands in contrast to most literature syntheses of 2-amino-2-deoxyhexose derivatives, as these generally employ glycals or hexoses as starting materials. This strategy may serve as a template for the assembly of many other 2-amino-2-deoxyhexoses with protection patterns difficult to access by conventional methods.
Description
This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, Copyright © 2023 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.2c02346.
Date
2023-01-17
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American Chemical Society
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Keywords
Cyclization, Layers, Lipids, Mixtures, Silica
Citation
Paul, D., Mague, J. T., & Sathyamoorthi, S. (2023). Sulfamate-Tethered Aza-Wacker Cyclization Strategy for the Syntheses of 2-Amino-2-deoxyhexoses: Preparation of Orthogonally Protected d-Galactosamines. The Journal of organic chemistry, 88(3), 1445–1456. https://doi.org/10.1021/acs.joc.2c02346
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