Journal
CARBOHYDRATE RESEARCH
Volume 339, Issue 18, Pages 2821-2833Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2004.10.002
Keywords
glycosyl carbarnates; carbohydrate-1-carbamates; glycosidation; disaccharides; one-pot reaction
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The syntheses of 44 1-carbamates from six different 1-O-unprotected carbohydrate derivatives (compounds 1-6), representing typical protecting pattern in glycoside synthesis, are described. The carbamate function is N-unsubstituted (compounds 1b-6b), mono- (compounds a: N-trichloroacetyl, c: N-monochloroacetyl, d: N-acetyl, e: N-ethyl, U N-allyl, g: N-phenyl) or disubstituted (compounds h: imidazolyl, i: N-diethyl, j: N-diphenyl). Additionally, three N-chlorosulfonyl carbarnates are synthesized and used as intermediates for the synthesis of N-unsubstituted compounds b. The accessibility of these compounds is described and compared. Some of the carbamates (1, 4, 5a-j) are used as model compounds for systematic investigations in glycoside syntheses. Selected experimental data (reaction conditions, anomeric ratios, rotation values, selected NMR data) are tabulated. (C) 2004 Elsevier Ltd. All rights reserved.
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