187031-74-9

Upstream product

• 100-39-0 benzyl bromide 
• 311797-09-8 methyl (benzyl 2-O-benzyl-β-D-galactopyranosid)uronate 
• 95722-13-7 1,2,3,4-tetra-O-acetyl-α-D-galactopyranosiduronic acid 
• 56768-32-2 1-bromo-2,3,4-tri-O-acetyl-α-D-galactopyranuronic acid methyl ester 
• 30628-07-0 1,2,3,4-tetra-O-acetyl-α-D-galactopyranosiduronic acid, methyl ester 
• 74801-06-2 benzyl 2,3-di-O-benzyl-4,6-ol-β-D-galactopyranoside 
• 311797-07-6 methyl (benzyl 2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosid)uronate 
• 71200-16-3 methyl (benzyl 3,4-O-isopropylidene-β-D-galactopyranosid)uronate 
• 71200-14-1 methyl (benzyl 2,3,4-tri-O-acetyl-β-D-galactopyranosid)uronate 
• 71200-15-2 methyl (benzyl β-D-galactopyranosid)uronate 
• 17120-54-6 benzyl 2,3-di-O-benzyl-β-D-galactopyranosiduronic acid 

Downstream Products

• 187031-93-2 C₆₁H₆₀O₁₃ 
• 187031-92-1 C₆₉H₆₈O₁₄ 
• 187031-90-9 C₆₆H₇₀O₁₄ 
• 187031-86-3 benzyl (methyl 2,3,4-tri-O-benzyl-α-D-galactopyranosyluronate)-(1->4)-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 

Relevant academic research and scientific papers

An efficient and highly stereoselective α(1 → 4) glycosylation between two D-galacturonic acid ester derivatives

The highly stereoselective α(1 → 4) coupling between two D-galacturonic acid ester derivatives was accomplished in good yields, for the first time, using a phenylthioglycoside as donor. The method was designed to prepare D-galacturonic acid oligomers with methyl ester groups in definite positions.

Synthesis of homogalacturonan fragments

Glycosylation of the D-galacturonic acid ester derivatives 15 and 17, which are prepared directly from D-galacturonic acid, with the thioglycosides 28 and 32, derived from the same sugar, provides α(1→4)-linked dimers. The formation of the glycosidic linkage between the galacturonic acid moieties is best achieved by iodonium di-sym-collidine perchlorate promotion. Thus, the 4'-O-p-methoxybenzyl dimer 38 can be obtained in 64% yield. Partial deprotection of the 4'-O-position provided the glycosyl acceptor 36, which was coupled with the donor 32 to yield the a(1''→4')-linked trimer 39 (48%). Approximately 8% of the β(1''→4')-coupled isomer was observed in the 13C NMR spectrum of the reaction mixture.

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.