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Constrained 3,6‐Anhydro‐Heptosides: Synthesis by a DAST‐Induced Debenzylative Reaction, and Reactivity Profile
Author(s) -
Tikad Abdellatif,
Vincent Stéphane P.
Publication year - 2013
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.201301071
Subject(s) - chemistry , reactivity (psychology) , glycosyl , anomer , glycosylation , intramolecular force , stereochemistry , bicyclic molecule , mannose , glycosyl donor , organic chemistry , medicine , biochemistry , alternative medicine , pathology
We report the first synthesis of a conformationally constrained 3,6‐anhydroheptoside analogue of D ‐ glycero ‐ D ‐ manno ‐heptopyranose 7‐phosphate by a DAST (diethylaminosulfur trifluoride)‐induced intramolecular cycloetherification. The reactivity of a series of constrained bicyclic 3,6‐anhydro‐thioheptosides as glycosyl donors was also studied in glycosylation reactions and compared with the reactivities of related unconstrained mannose and heptose scaffolds. Competition experiments confirmed that in the D ‐ manno ‐heptose series, a reversal of chair conformation leads to an enhancement of the anomeric reactivity.