191924-41-1

Upstream product

• 155135-78-7 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 121360-14-3 2-(trimethylsilyl)ethyl 3-O-benzyl-β-D-galactopyranoside 
• 191924-37-5 2-(trimethylsilyl)ethyl 3-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 117252-96-7 2-(trimethylsilyl)ethyl 4,6-di-O-benzylidene-β-D-galactopyranoside 
• 103082-76-4 2'-trimethylsilylethanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 117252-95-6 2-(trimethylsilyl)ethyl β-D-galactopyranoside 
• 191924-40-0 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranoside 

Downstream Products

• 909543-69-7 2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside 
• 211678-09-0 (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-3-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 211678-07-8 (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 260976-43-0 2-(trimethylsilyl)ethyl (6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-galactopyranoside 
• 260976-41-8 2-(trimethylsilyl)ethyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-β-D-galactopyranoside 
• 260976-40-7 2-(trimethylsilyl)ethyl 6-azido-2,3-di-O-benzyl-6-deoxy-β-D-galactopyranoside 
• 425623-88-7 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranosyl dibenzyl phosphateate 
• 425623-86-5 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-deoxy-4-O-(p-tolylsulfonyl)-β-D-galactopyranoside 
• 425623-87-6 2-(trimethylsilyl)ethyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-β-D-glucopyranoside 
• 425623-85-4 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-deoxy-β-D-galactopyranoside 
• 88773-22-2 4-azido-2,3-di-O-benzyl-4,6-dideoxy-β-D-glucopyranosyl trichloroacetimidate 
• 260976-39-4 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-p-toluenesulfonyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of globo- and isoglobotriosides bearing a cinnamoylphenyl tag as novel electrophilic thiol-specific carbohydrate reagents

The galactosyl donor, 4,6-di-O-acetyl-2,3-di-O-benzyl-d-galactopyranosyl trichloroacetimidate, was efficiently coupled with regioselectively benzylated lactoside acceptors under standard conditions to stereoselectively afford the corresponding globotrioside and isoglobotrioside derivatives in very good yields. These glycosides were smoothly functionalized with a 6-(p-cinnamoylphenoxy)-hexyl tether tag as novel electrophilic thiol-specific carbohydrate reagents. Immobilization of the globotrioside conjugate to Thiopropyl Sepharose 6B for purification of B-subunit of Shiga toxin (StxB) and coupling of a model cysteine-containing protein (StxB-Z(n)-Cys) to the isoglobotrioside conjugate were both performed with high efficiency.

Biosynthetic studies on the α-glucosidase inhibitor acarbose: The chemical synthesis of dTDP-4-amino-4,6-dideoxy-α-D-glucose

To study the biosynthesis of the pseudotetrasaccharide acarbose, dTDP-4-amino-4,6-dideoxy-α-D-glucose (3) was prepared from galactose in 16 steps. After initial protecting-group manipulations, the 6-position of galactose was deoxygenated by hydride displa

Synthesis of some amino and carboxy analogs of galabiose; evaluation as inhibitors of the pilus protein PapG(J)96 from Escherichia coli

The 2'-amino-2'-deoxy, 6-amino-6-deoxy, and 6-carboxy analogs of the reference inhibitor 2(trimethylsilyl)ethyl (α-D-galactopyranosyl)-(1→4)- β-d-galactopyranoside were synthesized and evaluated as inhibitors of the binding of the Escherichia coli-derived pilus protein PapG(J96), using an ELISA assay. The inhibitory efficiencies (K(rel); relative to the reference inhibitor) were: 157, 13, and 8, respectively. The results support the previously proposed combining site model, where the protein carries a negatively charged amino acid residue near HO-2' and HO-6 of the galabioside.

A synthetic approach to the c-series gangliosides containing sialyl-α(2 → 8) sialyl-α(2 → and) sialic acid: Synthesis of ganglioside GT4, α(2 → 6) GT4 and GT3

Trimeric sialic acid [Neu5Acα(2 → 8)Neu5Ac α(2 → 8)Neu5Ac, 1] residue-containing gangliosides, GT4, α(2 → 6)GT4 and GT3, have been synthesized for the first time. Methyl [phenyl 5-acetamido-8-O-[5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5 -dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylono- 1',9'-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D- glycero-α-D-galacto-2-nonulopyranosylono-1',9-lactone]-4,7-di-O-acetyl-3,5 -dideoxy-2-thio-D- glycero-D-galacto-2-nonulopyranosid]onate (3) was prepared from 1, via lactonization, methyl esterification of the carboxyl group at the reducting end, O-acetylation and conversion of the anomeric acetoxy group into a phenylthio group. Iodonium-promoted glycosylation of 3 with 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-β-D-galactopyranoside (5), 2-(trimethylsilyl)ethyl 3-O-benzyl-β-D-galactopyranoside (6), 2-(trimethylsilyl)ethyl 2-O-benzoyl-3-O-benzyl-β-D- galactopyranoside (9), and 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-galactopyranoside (11) gave the corresponding tetrasaccharides (13-15, 17) having the (Neu5Ac)3-Gal structure. The peracylated oligosaccharides 18 and 24 derived from 13 and 17, and the previously reported lactose derivative 29 were converted into the α-trichloroacetimidates 20, 26 and 31, and coupled with (2 S,3 R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (21) to afford the corresponding β-glycosides 22, 27 and 32. These protected azidosphingosine derivatives were each transformed into the target gangliosides GT4, α(2 → 6)GT4 and GT3 via selective reduction of the azido group, subsequent coupling with octadecanoic acid, O-deacylation and saponification of the methyl ester and lactone groups.