American Chemical Society
ol3c03106_si_001.pdf (3.09 MB)

De Novo Synthetic Approach to 2,4-Diamino-2,4,6-trideoxyhexoses (DATDH): Bacterial and Rare Deoxy-Amino Sugars

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Version 2 2023-10-20, 20:48
Version 1 2023-10-20, 16:12
journal contribution
posted on 2023-10-20, 20:48 authored by Olivea Vasquez, Angela Alibrandi, Clay S. Bennett
A synthetic route to 2,4-diamino-2,4,6-trideoxysugar stereoisomers in 6–7 steps and 22–33% overall yield is described. A key step in this pathway is the carbonyl coupling of d- and l-threoninol or d- and l-allo-threoninol to a phthalimido-allene mediated by chiral iridium-H8-BINAP, which allows for installation of two new chiral centers in one, highly diastereoselective (>20:1 dr) step. This approach provides a more concise, diastereoselective, and versatile method to access these deoxy-amino sugars than is currently available.