Glycosidation of 3,4,6-tri-o-benzyl-2-ethenyl-D-glucal - A route to 2-C-(β-methyl)methylene glycosides

Article abstract of DOI:10.1080/07328300008544109

Monosaccharidic and disaccharidic 2-C-(β-methyl)methylene glycosides were synthesized by an electrophilic conjugate addition reaction of ROH-type compounds in the presence of Ph₃⁺PH Br^- to 2-ethenyl-3,4,6-tri-O-benzyl-D-glucal 1, functioning as a model glycosyl donor. This 2-vinyl glucal derivative represents a series of 2-vinyl and 2-butadienyl glycals, prepared by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal. The exo-(β-methyl)methylene group paves the way for further chemical transformations.

Full text of DOI:10.1080/07328300008544109

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Glycosidation of 3,4,6-Tri-O-
Benzyl-2-Ethenyl-D-Glucal – A
Route to 2-C-(β-Methyl)Methylene
Glycosides
Ben-Ami Feit , Idil Kasuto Kelson , Anke Gerull , Sarah
Abramson & Richard R. Schmidt
a Raymond and Beverly Sackler Faculty of Exact Sciences
School of Chemistry , Tel-Aviv University , Israel
b Raymond and Beverly Sackler Faculty of Exact Sciences
School of Chemistry , Tel-Aviv University , Israel
c Faculty of Chemistry , Konstanz University , Konstanz,
Germany
d Raymond and Beverly Sackler Faculty of Exact Sciences
School of Chemistry , Tel-Aviv University , Israel
e Faculty of Chemistry , Konstanz University , Konstanz,
Germany
Published online: 27 Feb 2008.
To cite this article: Ben-Ami Feit , Idil Kasuto Kelson , Anke Gerull , Sarah Abramson & Richard
R. Schmidt (2000) Glycosidation of 3,4,6-Tri-O-Benzyl-2-Ethenyl-D-Glucal – A Route to 2-C-
(β-Methyl)Methylene Glycosides, Journal of Carbohydrate Chemistry, 19:6, 661-675, DOI:
10.1080/07328300008544109
To link to this article: http://dx.doi.org/10.1080/07328300008544109
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