| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346444 | Tetrahedron: Asymmetry | 2011 | 5 Pages |
Abstract
Efficient six-step protocols are described for the conversion of common disaccharides, such as maltose, cellobiose, or lactose, into the corresponding 4-O-glycosyl-1,5-anhydro-d-fructoses. Overall yields of 40–45% are favorably compared to the alternative eleven-step procedure from their monosaccharide components (∼15%).
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
3,6-Di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl)-1,5-anhydro-d-fructose E-oximeC24H33NO16[α]D20=-61.4 (c 1.0, CHCl3)Source of chirality: maltose
3,6-Di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-1,5-anhydro-d-fructose E-oximeC24H33NO16[α]D20=-25.9 (c 1.0, CHCl3)Source of chirality: cellobiose
Related Topics
Physical Sciences and Engineering
Chemistry
Inorganic Chemistry
Authors
Toshio Nakagawa, Frieder W. Lichtenthaler,