title: Synthesis of 2-iodoglycals, glycals, and 1,1'-disaccharides from 2-Deoxy-2-iodopyranoses under dehydrative glycosylation conditions.
abstract: Treatment of 2-deoxy-2-iodopyranoses under dehydrative glycosylation conditions afforded pyranose glycals, 2-iodoglycals, and 1,1'-disaccharides instead of the expected glycoside products. While the product distribution revealed that this reaction is very sensitive to the configuration of the 2-deoxy-2-iodopyranose, 2-iodopyranoid glycals can be obtained almost exclusively in good yields by employing 3,4-O-isopropylidene as a cyclic bifunctional protecting group. The behavior of 2-deoxy-2-iodopyranoses during the dehydrative elimination reaction has been analyzed in detail.
authors.affiliation: Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/ Marcel-lí Domingo s/n, 43007, Tarragona, Spain.
authors.forename: Miguel Angel
authors.initials: MA
authors.lastname: Rodríguez
authors.forename: Omar
authors.initials: O
authors.lastname: Boutureira
authors.forename: M Isabel
authors.initials: MI
authors.lastname: Matheu
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Díaz
authors.forename: Sergio
authors.initials: S
authors.lastname: Castillón
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004187:Disaccharides; D006027:Glycosides; D011714:Pyrans