Carbohydrates pp 113-142 | Cite as

Relative Reactivity of Hydroxyl Groups in Monosaccharides



The furanoid and pyranoid cyclic structures of monosaccharides generally may have four types of chemically distinguishable hydroxyl groups: (1) the anomeric (hemiacetal, lactol) hydroxyl group and (2) three types of alcoholic hydroxyl groups: (a) the primary hydroxyl group, which is always exocyclic with regard to the carbohydrate ring and is found in both hexopyranoses and pento- or hexofuranoses, (b) the endocyclic secondary hydroxyl groups found in both hexopyranoses and pento- or hexofuranoses, and (c) the exocyclic secondary hydroxyl groups found in hexofuranoses or in higher sugars containing hexopyranose ring.


Benzoyl Chloride Acyl Migration Tosyl Chloride Dibenzyl Ether Methanesulfonyl Chloride 
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Authors and Affiliations

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

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