259871-03-9

Upstream product

• 100-39-0 benzyl bromide 
• 220774-86-7 phenyl 1-thio-6-O-triphenylmethyl-β-D-galactopyranoside 
• 76-83-5 trityl chloride 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 

Downstream Products

• 38184-12-2 phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside 
• 259871-04-0 phenyl 2,3,4-tri-O-benzyl-6-O-succinoyl-1-thio-β-D-galactopyranoside 
• 259871-09-5 benzyl O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3',6'-succinate 
• 259871-05-1 phenyl 6-O-(2-O-benzoyl-1-O-benzyl-4,6-O-benzylidene-α-D-glucopyranos-3-yloxycarbonylpropanoyl)-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside 
• 259871-06-2 phenyl 6-O-(2-O-benzoyl-1,6-di-O-benzyl-α-D-glucopyranos-3-yloxycarbonylpropanoyl)-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside 
• 187031-78-3 methyl (phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate 
• 187031-76-1 tert-butyl (phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate 
• 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 
• 225640-42-6 benzyl (phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate 
• 225640-49-3 methyl (benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosyluronate)-(1->4)-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 
• 153440-04-1 C₁₀₈H₁₁₂O₂₀ 

Relevant academic research and scientific papers

Stereodirecting effect of the pyranosyl C-5 substituent in glycosylation reactions

(Chemical Equation Presented) The stereodirecting effect of the glycosyl C-5 substituent has been investigated in a series of D-pyranosyl thioglycoside donors and related to their preferred positions in the intermediate 3H4 and

Prearranged glycosides. Part 8. Intramolecular α-galactosylation via succinoyl tethered glycosides

Benzyl protected phenyl 1-thio-galactopyranoside donors which were tethered by a succinoyl linker at their positions 2 and 6, respectively, to position 3 of a blocked benzyl glucopyranoside acceptor with a 4-OH group solely afforded the corresponding α-(1→4)-linked disaccharides upon intramolecular glycosylation. 4,6-Siloxane protected mannosides react with rearrangement of the siloxane group under similar conditions.

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.