TMSCl as a mild and effective source of acidic catalysis in Fischer glycosidation and use of propargyl glycoside for anomeric protection.
Practical Fischer glycosidation was effected at room temperature or 60 degrees C by using 5 to 10 equiv. of TMSCl. The anomeric propargyl group formed by this method was found to be a versatile new protecting group, being stable in neat TFA but readily cleaved by treatment with Co2(CO)8 and TFA in CH2Cl2 via the formation of an alkyne-Co complex.
Izumi
Minoru
M
Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Japan.
Fukase
Koichi
K
Kusumoto
Shoichi
S
D000143:Acids / Q000737:chemistry; D002384:Catalysis; D005960:Glucosides / Q000737:chemistry*; D015394:Molecular Structure; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000143:Acids; D005960:Glucosides; D014297:Trimethylsilyl Compounds; C039293:trimethylchlorosilane