Regioselective one-pot protection of glucose.
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.
Wang
Cheng-Chung
CC
Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan.
Kulkarni
Suvarn S
SS
Lee
Jinq-Chyi
JC
Luo
Shun-Yuan
SY
Hung
Shang-Cheng
SC
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
D000438:Alcohols; D006027:Glycosides; D008698:Mesylates; D009005:Monosaccharides; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate; D005947:Glucose