Premium
How to Homologate Your Sugar: Synthetic Approaches to Septanosyl Containing Carbohydrates
Author(s) -
Vannam Raghu,
Peczuh Mark W.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600052
Subject(s) - chemistry , deoxyribose , nucleophile , electrophile , ring (chemistry) , glycosylation , carbohydrate chemistry , hexose , organic chemistry , ribose , stereochemistry , combinatorial chemistry , biochemistry , nucleic acid , catalysis , enzyme
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.