Synthesis of 5-thio-d-arabinose and 5-thio-d-lyxose and their methyl glycopyranosides

Autor: Neil A. Hughes, Namboole M. Munkombwe
Rok vydání: 1985
Předmět:
Zdroj: Carbohydrate Research. 136:397-409
ISSN: 0008-6215
DOI: 10.1016/0008-6215(85)85213-7
Popis: 1,2- O -Isopropylidene-5- O -toluene- p -sulphonyl-β- d -arabinofuranose has been converted into 5-thio- d -arabinose via 3- O -acetyl-5- S -acetyl-1,2- O -isopropylidene-5-thio-β- d -arabinofuranose. 5-Thio- d -lyxose was similarly obtained from methyl 2,3- O -isopropylidene-5- O -methanesulphonyl(or toluene- p -sulphonyl)-α- d -lyxofuranoside via methyl 5- S -acetyl(or benzoyl)-1,2- O -isopropylidene-5-thio-α- d -lyxofuranoside. The corresponding methyl thiopyranosides were obtained by methanolysis of the free sugars or the above thioester intermediates. All of the 5-thio- d -pentopyranoses and their methyl 5-thio- d -pentopyranosides are now known, and some of their properties are summarised.
Databáze: OpenAIRE