142330-02-7Relevant articles and documents
An alternative access to a trisaccharide repeating unit of the capsular polysaccharide of Streptococcus pneumoniae serotype 19A
Kaji, Eisuke,Osa, Yumiko,Tanaike, Mutsumi,Hosokawa, Yugo,Takayanagi, Hiroaki,Takada, Atsushi
, p. 437 - 440 (2007/10/03)
A chemical synthesis has been achieved for β-D-ManNAc-(1→4)-α-D-Glc- (1→3)-L-Rha, a trisaccharide repeating unit of the capsular polysaccharide of Streptococcus pneumoniae serotype 19A, by stepwise link-up of the suitably functionalized, constituent sugar units. A β-selective glycosylation of trimethylsilylethyl glucoside having free 4-OH with 2-(benzoyloxyimino)-2- deoxyglycosyl bromide, followed by manno-selective hydroboration, N- acetylation, and functionalization of the anomeric center (1-OSE→1-OH→1- F), gave a key disaccharide donor, β-D-ManNAc-(1→4)-α-D-Glc-(1→F. Ensuing glycosylation of an L-rhamnosyl acceptor with the donor substrate afforded, after deblocking, the target trisaccharide in 6.5% yield over 13 steps from D-glucose.
A practical synthesis of mannosaminyl-β(1 → 4)-glucosyl-α(1 → 2)-rhamnose, the trisaccharide repeating unit of a Streptococcus pneumoniae capsular polysaccharide
Kaji,Lichtenthaler,Osa,Takahashi,Zen
, p. 2401 - 2408 (2007/10/02)
An efficient chemical synthesis is described for the title trisaccharide repeating unit of the capsular polysaccharide of Streptococcus pneumoniae Type 19F. The key intermediate was a well-accessible indirect β-D-mannosaminyl donor, i.e. 2-(benzoyloxyimin
A Practical, Highly Stereoselective Synthesis of the Trisaccharide Repeating Unit of a Streptococcus pneumoniae Polysaccharide
Kaji, Eisuke,Lichtenthaler, Frieder W.,Osa, Yumiko,Takahashi, Keiko,Matsui, Eiko,Zen, Shonosuke
, p. 707 - 710 (2007/10/02)
A highly stereoselective method has been developed for the synthesis of the trisaccharide component of the capsular polysaccharide of Streptococcus pneumoniae type 19F.The key intermediate, 2-benzoyloxyiminoglycosyl bromide was successfully utilized for t