225640-45-9

Upstream product

• 186581-53-3 diazomethane 
• 725228-83-1 phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranosiduronic acid 
• 225640-43-7 tert-butyl (phenyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranosid)uronate 
• 124476-97-7 phenyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 231623-55-5 phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 225640-44-8 methyl (phenyl 2-O-benzyl-1-thio-β-D-galactopyranosid)uronate 

Downstream Products

• 725228-92-2 methyl (phenyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranosid)uronate 
• 225640-47-1 methyl (phenyl 2,3-di-O-benzyl-1-thio-4-O-trimethylsilyl-β-D-galactopyranosid)uronate 

Relevant academic research and scientific papers

Thioglycuronides: Synthesis and application in the assembly of acidic oligosaccharides

Partially protected thioglycuronic acids are prepared efficiently by chemo- and regioselective oxidation of the corresponding thioglycosides using the TEMPO/BAIB reagent combination. After esterification, the thioglycuronic acids proved to be useful as both donor and acceptor in sulfonium-mediated condensations toward acidic di- and trisaccharides.

Synthesis of the two monomethyl esters of the disaccharide 4-O-α-D-galacturonosyl-D-galacturonic acid and of precursors for the preparation of higher oligomers methyl uronated in definite sequences

Methyl (α-D-galactopyranosyluronic acid)-(1→4)-D-galactopyranuronate and methyl α-D-galactopyranosyluronate-(1→4)-D-galactopyranuronic acid have been synthesized by coupling methyl (benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate (3) or benzyl (benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate (4) with benzyl (phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate and methyl (phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate, respectively, using N-iodosuccinimide and trifluoromethanesulphonic acid as promoters, followed by removal of the benzyl groups. The 4'-OH unprotected dimers benzyl (methyl 2,3-di-O-benzyl-α-D-galactopyranosyluronate)-(1→4)-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate and methyl (benzyl 2,3-di-O-benzyl-α-D-galactopyranosyluronate)-(1→4)-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate were prepared from methyl (phenyl 2,3-di-O-benzyl-1-thio-4-O-trimethylsilyl-β-D-galactopyranosid)uronate and benzyl (phenyl 2,3-di-O-benzyl-1-thio-4-O-trimethylsilyl-β-D-galactopyranosid)uronate and acceptors 4 or 3, respectively. These compounds have been designed to serve as precursors for the preparation of higher-membered d-galacturonic acid oligomers methyl esterified in definite positions. Copyright (C) 1998 Elsevier Science Ltd.