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- W2950581105 abstract "Abstract UV light-promoted reduction of acetobromoglucose by NaBH3CN 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 NaBH3CN compared to NaBH4 or NaBD4, and do not occur with acetochloroglucose. Similar reductions to 1,3,4,6-tetra-O-acetyl-2-deoxy-α- d -arabino-hexopyranose were achieved upon heating to 80 °C t-BuOH or CH3CN solutions of NaBH3CN and AIBN, but with a lower selectivity due to competing ionic reactions. With other pyranosyl bromides, reductions by NaBH3CN could be tuned similarly ( d -galacto), but some ( d -manno, 5-thio- d -xylo) gave mainly or exclusively 1,5-anhydro-itols. Other conditions, or reagents promoting SET process, afforded also reduced products, but with lower rates or selectivities. Primary iodides were reduced readily with NaBH3CN under UV light." @default.
- W2950581105 created "2019-06-27" @default.
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- W2950581105 date "2013-11-01" @default.
- W2950581105 modified "2023-09-25" @default.
- W2950581105 title "NaBH3CN 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 or 1,5-anhydro-itols" @default.
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- W2950581105 doi "https://doi.org/10.1016/j.tet.2013.09.032" @default.
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