211678-07-8

Upstream product

• 211678-06-7 (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 117253-15-3 2-(trimethylsilyl)ethyl 2-O-benzyl-3,4-O-isopropylidene-6-O-(2-methoxyisopropyl)-β-D-galactopyranoside 
• 117253-14-2 2-(trimethylsilyl)ethyl 3,4-O-isopropylidene-6-O-(2-methoxyisopropyl)-β-D-galactopyranoside 
• 191924-41-1 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-galactopyranoside 

Downstream Products

• 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 

Relevant academic research and scientific papers

Synthesis of building blocks for an iterative approach towards oligomers of the Streptococcus pneumoniae type 1 zwitterionic capsular polysaccharide repeating unit

Zwitterionic capsular polysaccharide extracts, 8 kDa in mass, from Streptococcus pneumoniae type 1 (Spt1) have shown unique T-cell activating properties. Oligomers of the trisaccharide repeating unit of the Spt1 capsular polysaccharide [3)-4-NH2-α-d-QuipNAc-(14)-α-d-GalpA-(13)-α-d-GalpA-(1-]n of defined length are needed to further investigate this response. An approach towards iteratively extendable trisaccharide building blocks of the zwitterionic capsular polysaccharides of Spt1 is described. Key elements include the comparison of pre-glycosylation oxidation and post-glycosylation oxidation approaches using thioglycoside donors to the target trisaccharide, the optimisation of the post-glycosylation oxidation approach, and the conversion of the trisaccharide to building blocks tailored for iterative glycosylation. The construction and evaluation of stereotunable 2-N-3-O-oxazolidinone donors for the common bacterial 2-acetamido-4-amino-2,4,6-trideoxy-α-d-galactopyranoside motif is also described, as is a key intermediate for their efficient synthesis.

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.