Reductive Opening of Sugar Epoxides by Diborane-Borohydride Ion

Article abstract of DOI:10.1021/jo01307a021

Carbohydrate epoxides were reduced selectively in the presence of sulfonyl ester, ketal, and acetal groups.Unlike more conventional reagents, such as aluminum hydride, alkoxyaluminum hydrides, and Raney nickel, this reagent permits the presence of a trans-(arylsulfonyl)oxy group adjacent to the epoxide ring.The regioselectivity of the ring-opening reaction appears to be controlled primarily by the steric and polar factors.