Abstract
This protocol describes the O-glycosyl trichloroacetimidate-based glycosylation of protected galactal 1 as acceptor under Sn(OTf)(2) catalysis to give disaccharide 4. Nitration of the galactal moiety using nitric acid-acetic acid as nitrating agent followed by base-promoted acetic acid elimination affords the 2-nitro derivative 6 in a one-pot procedure. These types of intermediates can be used in the stereoselective synthesis of glycosides via Michael-type addition of alcohols as nucleophiles to 2-nitroglycals. Here, the base-catalyzed alpha-selective addition of N-Boc-protected Ser and Thr esters (7a, b) is described, which leads stereoselectively to adducts 8a, b. Transformation into the corresponding 2a-acetylamino derivates 9a, b provides versatile mucin core 1 building blocks (the total time for synthesizing 9a, b starting from 1 to 2 is typically 7 d with an overall yield of 18-25%). Also various other types of nucleophiles are amenable to this Michael-type addition 2-nitroglycals.
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