How to Homologate Your Sugar: Synthetic Approaches to Septanosyl Containing Carbohydrates. Issue 10 (8th March 2016)

• Record Type: Journal Article
• Authors: Vannam, Raghu; Peczuh, Mark W.
• Is Part Of: European journal of organic chemistry. Issue 10(2016)
• Page Start: 1800
• Page End: 1812
• Publication Date: 2016-03-08
• Subjects: Synthetic methods -- Glycosylation -- Carbohydrates -- Homologation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600052
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Seven‐membered ring "septanose" sugars have been used as surrogates of pyranoses in biochemical investigations. Septanoses are homologs of pyranoses in the same way that beta amino acids are for alpha amino acids or hexose nucleosides for deoxyribose nucleosides. Methods for their synthesis have undergone significant development recently, following two complementary strategies. In one, glycals are cyclopropanated which are later opened in addition reactions with nucleophiles. The other follows traditional glycosylation strategies where electrophilic donors are prepared and reacted with nucleophiles. Unsaturated seven membered ring oxepines play a key role in both of the approaches, which are highlighted. Abstract : Synthetic methods for the homologation of pyranose sugars to their seven membered ring septanose counterparts are presented. Two main methods for ring expansion are presented, with carbohydrate based oxepines playing a key role to each. Photo © Linda Bucklin/123RF used with permission.