The synthesis of carbohydrates can be particularly diffi

Chapter 15, Problem 15.25

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The synthesis of carbohydrates can be particularly diffi cult because of the large number of chiral centers and OH functional groups present. Epoxides can be useful synthetic intermediates in carbohydrate syntheses. Draw the product of the following reactions of a Gilman reagent with each epoxide. (a) 1. Me2CuLi Ether 40C 2. H2O, HCl O O OH (b) 1. Me2CuLi Ether 78C to 40C 2. H2O, HCl O O O

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