A facile synthesis of 5-thio-l-fucose and 5-thio-d-arabinose from d-arabinose

✍ Scribed by Masayuki Izumi; Osamu Tsuruta; Hironobu Hashimoto

• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 955 KB
• Volume: 280
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)00323-1

✦ Synopsis

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 achieved to give the corresponding 6-deoxy-/3-o-altrofuranose isomer in good yield. A sulfur atom was introduced at C-5 of 6-deoxy-~altrofuranose derivatives via substitution of a 5-tosylate with KSAc in HMPA with inversion of configuration, giving 5-thio-L-fucopyranose. A 3-O-substituted-L-fucose derivative was also prepared from 6-deoxy-fl-D-altrofuranose derivatives. 5-Thio-D-arabinopyranose tetraacetate, the 5-demethyl analog of 5thio-L-fucose, was also synthesized from 5-O-trityl-D-arabinofuranose in 5 steps. 5-Thio-oarabinose showed weak inhibitory activity against a-L-fucosidase from bovine kidney (K i = 0.77 raM).