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De Novo Synthetic Approach to 2,4-Diamino-2,4,6-trideoxyhexoses (DATDH): Bacterial and Rare Deoxy-Amino Sugars
Olivea Vasquez1, Angela Alibrandi1, Clay S Bennett1
1Department of Chemistry, Tufts University, 62 Talbot Avenue, Medford, Massachusetts 02155, United States.
Abstract:
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.
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