71200-15-2

Upstream product

• 71200-14-1 methyl (benzyl 2,3,4-tri-O-acetyl-β-D-galactopyranosid)uronate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 100-51-6 benzyl alcohol 
• 4304-12-5 benzyl β-D-galactopyranoside 
• 130506-35-3 benzyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-galactopyranoside 
• 10343-13-2 benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 30628-07-0 1,2,3,4-tetra-O-acetyl-α-D-galactopyranosiduronic acid, methyl ester 
• 56768-32-2 1-bromo-2,3,4-tri-O-acetyl-α-D-galactopyranuronic acid methyl ester 
• 95722-13-7 1,2,3,4-tetra-O-acetyl-α-D-galactopyranosiduronic acid 

Downstream Products

• 17120-56-8 methyl (benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 
• 187031-74-9 benzyl (benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 
• 311797-09-8 methyl (benzyl 2-O-benzyl-β-D-galactopyranosid)uronate 
• 311797-07-6 methyl (benzyl 2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosid)uronate 
• 311797-23-6 methyl (2,3,4-tri-O-benzyl-α-D-galactopyranosyluronic acid)-(1->4)-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 
• 130506-38-6 methyl (benzyl 2-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosid)uronate 
• 71200-16-3 methyl (benzyl 3,4-O-isopropylidene-β-D-galactopyranosid)uronate 

Relevant academic research and scientific papers

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.

D-Galactose-derived D-galacturonic acid derivatives suitable as glycosyl acceptors

Allyl (1a) and benzyl (1b) β-D-galactopyranosides were converted into methyl uronates, (6a and 6b) by three different routes.The carboxyl group was introduced by Jones oxidation of suitable protected precursors and esterified directly.The chemical behaviour of 6-O-trityl-, 6-O-(4,4'-dimethoxytrityl)-, and 6-O-(2-methoxypropane-2-yl)-derivatives was investigated.The overall yields obtained were strongly influenced by the protecting groups used, in particular their stability in acidic solution.