Synthesis of 2-iodoglycals, glycals, and 1,1'-disaccharides from 2-Deoxy-2-iodopyranoses under dehydrative glycosylation conditions.
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.
Rodríguez
Miguel Angel
MA
Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/ Marcel-lí Domingo s/n, 43007, Tarragona, Spain.
Boutureira
Omar
O
Matheu
M Isabel
MI
Díaz
Yolanda
Y
Castillón
Sergio
S
Seeberger
Peter H
PH
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
D004187:Disaccharides; D006027:Glycosides; D011714:Pyrans