183239-79-4

Upstream product

• 600-22-6 pyruvic acid methyl ester 
• 183239-78-3 Allyl 3-O-benzoyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 
• 172490-46-9 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 183388-21-8 allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 
• 183239-77-2 Allyl 3-O-benzoyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 
• 188583-14-4 allyl-2-N-Troc-2-deoxy-α-D-glucopyranoside 

Relevant academic research and scientific papers

Prearranged glycosides, 4: Synthesis via prearranged glycosides of a tetrasaccharide fragment related to the capsular polysaccharide of Streptococcus pneumoniae type 27

The blockwise synthesis of the pyruvated tetrasaccharide 4,6-(S)-pyruvic-acetal-β-D-GlcNAcp-(1→3)-α-D-Gal p-(1→4)-β-L-Rhap-(1→4)-β-D-Glc p-O(CH2)5NH2 (32), related to the repeating unit of the capsular polysaccharide of Streptococcus pneumonias type 27, by coupling of the suitably protected disaccharide blocks 4,6-(S)-pyruvic-acetal-β-D-GlcNAcp-(1→3)-α-D-Gal p-trichloroacetimidate (13) and β-L-Rhap-(1→4)-β-D-Glcp-O(CH 2)5NHZ (29β) is described. The latter disaccharide acceptor was prepared via prearranged glycosides by intramolecular glycosylation of a protected 5-aminopentyl β-D-glucopyranoside linked by a succinyl bridge at C-3 to C-2 of ethyl 1-thio-α-L-rhamnopyranoside. The dependence of the anomeric selectivity of the coupling on the nature of the protecting group at C-4 of the rhamnosyl moiety is studied. VCH Verlagsgesellschaft mbH, 1996.