155135-91-4

Upstream product

• 155135-83-4 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside 
• 133198-04-6 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside 
• 117253-26-6 2-(trimethylsilyl)ethyl O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of the saccharide moiety of galactosylgloboside (SSEA-3) and its conjugation to bovine serum albumin and Sepharose

The pentasaccharide glycoside corresponding to galactosylgloboside (SSEA-3), β-D-Gal p-(13)-β-D-Gal pNAc-(13)-α-D-Gal p-(14)-β-D-Gal p(14)-β-D-Glc p-1-OCH2CH2Si(CH3)3 (4), was synthesized via glycosylation (87percent) of 2-(trimethylsilyl)ethy

Synthesis of the globotetraose tetrasaccharide and terminal tri- and di-saccharide fragments

The 2-(trimethylsilyl)ethyl (TMSEt) β-glycosides of globotetraose 3)-α-D-Gal-(1 -> 4)-β-D-Gal-(1 -> 4)-D-Glc> and the terminal trisaccharide, as well as the methyl α-glycoside 1 of the terminal disaccharide, were synthesised by silver trifluoromethanesulfonate-promoted β-glycosylation of suitably protected galactoside, galabioside, and globotrioside alcohols with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl chloride, followed by removal of protecting groups.Removal of the anomeric TMSEt group of the globotetraoside and of the terminal trisaccharide, using trifluoroacetic acid-dichloromethane, gave the corresponding hemiacetal sugars 8 and 3.The TMSEt glycoside of the terminal trisaccharide was converted, via the 1-acetate, into the corresponding isobutyl (4) and 3-butylsulfonyl-2-propyl (5) glycosides and into the TMSEt thioglycoside 6 via the glycosyl bromide.