Journal of Organic Chemistry p. 7328 - 7334 (1992)
Update date:2022-08-04
Topics:
Knapp, Spencer
Naughton, Andrew B. J.
Jaramillo, Carlos
Pipik, Brenda
Reaction of pyranoside diol (equatorial) monotriflates with soft, nonbasic nucleophiles is a useful way to make axial heteroatom-substituted and "epimerized" pyranosides, particularly where a fused acetal ring inhibits ring contraction.Among the substrates examined (1,2,3,4,35), only 4 shows a strong tendency to give ring-contracted products.The reaction of 1-3 with more basic nucleophiles (F(1-), t-BuO(1-)) leads to the anhydrosugars 8, 25, and 26, respectively.The SN2 reaction of 35 with tetra n-butylammonium iodide forms the basis for a new synthesis of the Cerny epoxide 32.
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