title: General Homologation Strategy for Synthesis of L-glycero- and D-glycero-Heptopyranoses.
abstract: A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed α-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The L-glycero- and D-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of L/D-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.
authors.affiliation: Applied Chemistry Department, National Chiao Tung University , 1001 University Road, Taiwan 300, R.O.C.
authors.forename: Shaheen K
authors.initials: SK
authors.lastname: Mulani
authors.affiliation: Applied Chemistry Department, National Chiao Tung University , 1001 University Road, Taiwan 300, R.O.C.
authors.forename: Kuang-Chun
authors.initials: KC
authors.lastname: Cheng
authors.affiliation: Applied Chemistry Department, National Chiao Tung University , 1001 University Road, Taiwan 300, R.O.C.
authors.forename: Kwok-Kong T
authors.initials: KK
authors.lastname: Mong
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry; D006539:Heptoses / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D006027:Glycosides; D006539:Heptoses