Open AccessTMSCl as a Mild and Effective Source of Acidic Catalysis in Fischer Glycosidation and Use of Propargyl Glycoside for Anomeric Protection
Author(s) -
Minoru Izumi,
Koichi Fukase,
Shoichi Kusumoto
Publication year - 2002
Publication title -
bioscience biotechnology and biochemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.509
H-Index - 116
eISSN - 1347-6947
pISSN - 0916-8451
DOI - 10.1271/bbb.66.211
Subject(s) - anomer , propargyl , alkyne , chemistry , glycoside , catalysis , combinatorial chemistry , organic chemistry
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.
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