The mild cleavage of 2-amino-2-deoxy-D-glucoside methoxycarbonyl derivatives.
The conversion of methyl carbamate to the corresponding free amine is described for a series of 2-amino-2-deoxy-D-glucosamine derivatives. Cleavage of methoxycarbonyl moiety with MeSiCl(3) and triethylamine in dry THF at 60 degrees C and subsequent aqueous hydrolysis yields the free amine in 54 to 93% yields. The selective cleavage of methyl carbamates with MeSiCl(3) in the presence of a 2,2,2-trichloroethoxycarbonyl group or 2-azido glycosides affords selectively, orthogonal N-deprotected carbohydrates.
Yeung
B K
BK
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
Adamski-Werner
S L
SL
Bernard
J B
JB
Poulenat
G
G
Petillo
P A
PA
D002384:Catalysis; D005960:Glucosides / Q000737:chemistry*; D006868:Hydrolysis; D008759:Methylglycosides / Q000737:chemistry*
D005960:Glucosides; D008759:Methylglycosides