Synthesis of 2-iodoglycals, glycals, and 1,1'-disaccharides from 2-Deoxy-2-iodopyranoses under dehydrative glycosylation conditions.

Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/ Marcel-lí Domingo s/n, 43007, Tarragona, Spain.
The Journal of Organic Chemistry (Impact Factor: 4.64). 12/2007; 72(23):8998-9001. DOI: 10.1021/jo701738m
Source: PubMed

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.

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Available from: Omar Boutureira, May 04, 2015