title: Synthesis of 6-deoxy-L-idose and L-acovenose from 1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranose.
abstract: A practical route toward the synthesis of 6-deoxy-L-idose and L-acovenose from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose is described. Key steps include the stereoselective hydrogenation of 6-deoxy-1,2:3,5-di-O-isopropylidene-alpha-D-xylo-hex-5-enofuranose, regioselective protection of 6-deoxy-1,2-O-isopropylidene-beta-L-idofuranose at 0-5, and epimerisation of 6-deoxy-5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-beta-L-idofuranose at C-3.
authors.affiliation: Institute of Chemistry, Academia Sinica, Taipei, Taiwan, ROC. schung@chem.sinica.edu.tw
authors.forename: S C
authors.initials: SC
authors.lastname: Hung
authors.forename: S R
authors.initials: SR
authors.lastname: Thopate
authors.forename: R
authors.initials: R
authors.lastname: Puranik
mesh_terms: D003837:Deoxy Sugars / Q000138:chemical synthesis*; D005947:Glucose / Q000031:analogs & derivatives / Q000737:chemistry*; D006601:Hexoses / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C438083:6-deoxy-idose; D003837:Deoxy Sugars; D006601:Hexoses; C438084:acovenose; C036124:1,2-5,6-di-O-isopropylidene-D-glucofuranose; C011754:6-deoxytalose; D005947:Glucose