Reactions of some pyranoside diol monotriflates with nucleophiles and bases

S Knapp, ABJ Naughton, C Jaramillo…

Index: Knapp, Spencer; Naughton, Andrew B. J.; Jaramillo, Carlos; Pipik, Brenda Journal of Organic Chemistry, 1992 , vol. 57, # 28 p. 7328 - 7334

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Citation Number: 40

Abstract

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 (P, t-BuO-) leads to the anhydrosugars 8, 25, and 26, ...