1046465-49-9Relevant academic research and scientific papers
Synthesis of a tetrasaccharide phosphate from the linkage region of the arabinogalactan-peptidoglycan complex in the mycobacterial cell wall
Lee, Yong Joo,Fulse, Dinanath Baburao,Kim, Kwan Soo
, p. 1574 - 1584 (2008/12/21)
The synthesis of dibenzyl 6-O-naphthylmethyl-2,3,5-tri-O-benzoyl-β-d-galactofuranosyl-(1→5)-2,3-di-O-benzoyl-6-O-benzyl-β-d-galactofuranosyl-(1→4)-3-O-benzyl-2-O-pivaloyl-α-l-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-4,6-di-O-benzoyl-α-d-glucopyranosyl phosphate (1), a protected form of the tetrasaccharide phosphate of the linkage region of the arabinogalactan-peptidoglycan complex in the mycobacterial cell wall, has been accomplished. Key steps include the coupling of four monosaccharide building blocks with complete stereoselectivity by glycosylations employing thioglycosides, 2′-carboxybenzyl glycosides, and glycosyl fluorides as glycosyl donors. The α-glycosyl phosphate linkage was also stereoselectively elaborated by reaction of a tetrasaccharide hemiacetal with tetrabenzyl pyrophosphate in the presence of a base.
