Synthesis of methyl α- and β-D-gulopyranosiduronic acids
✍ Scribed by Thorleif Anthonsen; Mohammed A.E. Sallam
- Publisher
- Elsevier Science
- Year
- 1980
- Tongue
- English
- Weight
- 170 KB
- Volume
- 78
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
The synthesis of glycosides of uronic acids by catalytic air-oxidation of glycosides of the corresponding aldoses has been reviewed by Heyns and Paulsen ~. Methyl ~-and /l-D-gulopyranosiduronic acids• required for a study of lanthanide-induced shifts in the n.m.r, spectra of carbohydrates, may be prepared as their ammonium salts by catalytic air-oxidation of the corresponding, neutral methyl gulosides 2. However, since the methyl ~-and /,~-D-gulosides were not readily available, we now report the preparation of the uronic acid glycosides froni D-glycera-D-gulo-heptose (1),
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The title branched-trisaccharide derivatives (9 and 13) have been synthesised from methyl 2,3-O-(2-nitrobenzylidene)-a-L-rhamnopyranoside (2) using the 2nitrobenzylidene residue as a temporary blocking-group. Condensation of 2 with methyl (2,3,4-tri-O-acetyl-a-D-glucopyranosyl bromide)uronate afford