769920-63-0Relevant academic research and scientific papers
Synthesis of various sulfoforms of the trisaccharide β-D-GlcpA-(1→3)-β-D-Galp-(1→3)-β-D-Galp-(1→OMP) as probes for the study of the biosynthesis and sorting of proteoglycans
Thollas, Bertrand,Jacquinet, Jean-Claude
, p. 434 - 442 (2007/10/03)
A straightforward preparation of various sulfoforms of the trisaccharide 4-methoxyphenyl O-(sodium β-D-glucopyranosyluronate)-(1 → 3)-(β-D-galactopyranosyl)-(1 → 3)-β-D-galactopyranoside (1), namely its 6a- and 4a-monosulfate, 6b- and 4b-monosulfate and 6a,6b-disulfate derivatives, is reported/or the first time. These compounds, which are partial structures of the linkage region of proteoglycans, will serve as probes for the study of the biosynthesis and sorting of these macromolecules. A key trisaccharide derivative, in which the two similar D-Gal units were differentiated at C-4,6 with 4,6-benzylidene and 4,6-di-tert-butylsilylene acetals, respectively, was used as a common intermediate. Both acetal groups showed excellent orthogonality, and allowed the preparation of all target compounds in high yield. Noteworthy is the possibility to prepare the 6a- and 6b-monosulfated and the 6a,6b-disulfated species through a one-pot regioselective procedure starting from a tetrol precursor.
