An efficient route toward 2-amino-beta-D-galacto- and -glucopyranosides via stereoselective Michael-type addition of 2-nitroglycals.
Under the catalysis of DMAP or PPY in CH(2)Cl(2), the Michael-type addition of nucleophiles to 2-nitrogalactal or 2-nitroglucal leads in excellent yields and stereoselectivity to the corresponding beta-galacto- or -glucopyranosides, which are ready precursors to the biologically significant beta-d-galactosamine and -glucosamine units.
Xue
Weihua
W
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Sun
Jiansong
J
Yu
Biao
B
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism
D005960:Glucosides; D011714:Pyrans