Efficient synthesis of triazoles from d-arabinose and l-fucose
โ Scribed by Timo Flessner; Chi-Huey Wong
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 71 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The efficient synthesis of sugar-derived triazoles via a one-pot substitution-cyclization-oxidation procedure is presented. Starting from D-arabinose and L-fucose, triazole structures as potential enzyme inhibitors were obtained in six to eight steps.
๐ SIMILAR VOLUMES
5-Thio-L-fucopyranose tetraacetate was synthesized in 11 steps from 5-O-trityl-D-arabinofuranose or D-arabinose diethyl dithioacetal by one-carbon elongation at C-5. Highly diastereoselective addition of MeLi in ether to a 1,2-O-isopropylidene-[J-D-arabino-pentodialdo-l,4-furanose derivative was ach
L-Fucose (4), a sugar widespread in Nature ', has lately acquired special significance as a constituent of several families of blood-group antigens'. L-Fucose is either the immunodominant sugar of complex carbohydrate antigens, or its presence may increase the strength of the antigenic response. Its
## Abstract LโGlucose derivatives are prepared by two different routes. The first involves a modification of the previously reported multiโstep approach by __Shiozaki__^8^, starting from a Dโglucuronoโ1,5โlactone derivative, resulting in the isolation of 2,3,4,6โtetraโ__O__โbenzylโLโglucopyranose.