Carbohydrates pp 291-321 | Cite as

Addition of Nucleophiles to Glycopyranosiduloses

  • Momcilo Miljković


Two distinct types of interactions control the stereochemistry of nucleophilic addition to glycopyranosiduloses. One is the classical nonbonded steric interaction and torsional strain between the incoming nucleophile and substituents on a pyranoside ring. These types of interactions are typical for all polysubstituted six-membered cyclic compounds. The second type of interaction is the electrostatic (dipolar) or electronic interaction between the incoming nucleophile and the glycosidic and/or the ring oxygen and is typical for carbohydrates. We will illustrate these by examining the stereochemistry of addition of various nucleophiles to the carbonyl carbon of glycopyranosid-2-, 3-, and 4-ulose of both α- and β-anomers.


Carbonyl Carbon Metal Hydride Oxirane Ring Torsional Strain Ethyl Bromoacetate 
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Authors and Affiliations

  1. 1.Department of Biochemistry & Molecular BiologyPennsylvania State UniversityHersheyUSA

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