An expeditious preparation of various sulfoforms of the disaccharide beta-D-Galp-(1-->3)-D-Galp, a partial structure of the linkage region of proteoglycans, as their 4-methoxyphenyl beta-D-glycosides.
An expeditious preparation of various sulfoforms of the disaccharide 4-methoxyphenyl O-(beta-D-galactopyranosyl)-(1-->3)-beta-D-galactopyranoside, namely the 4(I)- and 6(I)-sulfate, the 4(II)- and 6(II)-sulfate, and the 6(I),6(II)-disulfate derivatives, is reported for the first time. These molecules will be useful for the study of the early steps of the biosynthesis and sorting of proteoglycans. All target compounds were readily obtained from the common key intermediate 4-methoxyphenyl O-(2,3-di-O-benzoyl-4,6-di-O-levulinoyl-beta-D-galactopyranosyl)-(1-->3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-galactopyranoside, easily prepared from the common starting material 4-methoxyphenyl 4,6-O-benzylidene-beta-D-galactopyranoside. Noticeable is the possible preparation of the different 6-O-sulfonated species through a one-pot procedure starting from a tetrol precursor.
Jacquinet
Jean-Claude
JC
Institut de Chimie Organique et Analytique, UMR CNRS 6005, UFR Faculté des Sciences, Université d'Orléans, BP 6759, F-45067 Cedex, Orléans, France.
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D005697:Galactosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011509:Proteoglycans / Q000737:chemistry*; D013457:Sulfur Compounds / Q000138:chemical synthesis*
D004187:Disaccharides; D005697:Galactosides; D011509:Proteoglycans; D013457:Sulfur Compounds