title: Regioselective one-pot protection of glucose.
abstract: Detailed protocols for the regioselective protection of individual hydroxyls in monosaccharide units are described here. This expedient methodology incorporates up to seven reaction sequences, obviating the necessity to carry out intermittent tedious work-ups and time-consuming purifications. Using this TMSOTf-catalyzed one-pot protocol, the 2,3,4,6-tetra-O-trimethylsilylated hexopyranosides bearing an anomeric group could be transformed into a whole set of differentially protected 2-alcohols, 3-alcohols, 4-alcohols, 6-alcohols and fully protected monosaccharides in high yields. These tailor-made glycosyl donors and acceptors can then be used for stereoselective one-pot glycosylation for oligosaccharide synthesis. The total time for the preparation of a purified protected sugar unit ranges between 1 and 2 d. This process would otherwise take 1-2 weeks.
authors.affiliation: Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan.
authors.forename: Cheng-Chung
authors.initials: CC
authors.lastname: Wang
authors.forename: Suvarn S
authors.initials: SS
authors.lastname: Kulkarni
authors.forename: Jinq-Chyi
authors.initials: JC
authors.lastname: Lee
authors.forename: Shun-Yuan
authors.initials: SY
authors.lastname: Luo
authors.forename: Shang-Cheng
authors.initials: SC
authors.lastname: Hung
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis; D002621:Chemistry / Q000295:instrumentation / Q000379:methods; D002855:Chromatography, Thin Layer; D005947:Glucose / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D006027:Glycosides / Q000138:chemical synthesis; D008698:Mesylates / Q000737:chemistry; D009005:Monosaccharides / Q000138:chemical synthesis*; D014297:Trimethylsilyl Compounds / Q000737:chemistry
chemical_list: D000438:Alcohols; D006027:Glycosides; D008698:Mesylates; D009005:Monosaccharides; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate; D005947:Glucose