NaBH 3 CN and other systems as substitutes of tin and silicon hydrides in the light or heat-initiated reduction of halosugars: a tunable access to either 2-deoxy sugars …
I Bruyere, Z Toth, H Benyahia, JL Xue, JP Praly
Index: Bruyere, Isabelle; Toth, Zoltan; Benyahia, Hamida; Xue, Jia Lu; Praly, Jean-Pierre Tetrahedron, 2013 , vol. 69, # 46 p. 9656 - 9662
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Abstract
Abstract UV light-promoted reduction of acetobromoglucose by NaBH 3 CN in t-BuOH afforded 1, 3, 4, 6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose in high yield and purity, via a Surzur–Tanner rearrangement, while, with 10 mol% thiophenol added, acetylated 1, 5- anhydro-d-glucitol was cleanly obtained. Such tin-free and mild reductions, presumed to proceed via radical pathways, were more efficient with NaBH 3 CN compared to NaBH 4 ...
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