206649-90-3

Upstream product

• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-galactopyranose 
• 138811-45-7 1,2,3,5,6-penta-O-benzoyl-D-galactofuranose 
• 33423-31-3 benzyl 2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside 
• 206649-89-0 benzyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 206649-93-6 N-[(2S,3R,4R,5S,6R)-2-Benzyloxy-5-[(2S,3R,4R,5S)-5-((R)-1,2-dihydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-4-hydroxy-6-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide 

Relevant academic research and scientific papers

One-pot synthesis of β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]-D-GlcNac, a 'core' trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi

Tin(IV) chloride-promoted condensation of benzyl 2-acetamido-3-O- benzoyl-2-deoxy-α-D-glucopyranoside (4) with penta-O-benzoyl-β-D- galactopyranose (6) gave the derivative of β-D-Galp-(1 → 6)-α-D-GlcNAc 7 in 80% yield. This was glycosylated with penta-O-benzoyl-α,β-D- galactofuranose (5), employing the same catalyst, to afford the protected benzyl per-O-benzoyl-β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]D-GlcNAc 10 in 41% yield. Alternatively, compound 10 was obtained directly in a one-pot reaction from 4, by sequential addition of 6 and 5 (34% yield). β-Glycosidic linkages were diastereoselectively formed. De-O-benzoylation of 10, followed by heterogeneous catalytic transfer hydrogenolysis of the benzyl group afforded the free trisaccharide β-D-Galf(1 → 4)[ β-D-Galp(l → 6)]-D-GlcNAc (14) in 98% yield from 10. Sodium borohydride reduction of 14 gave the corresponding alditol, whose spectral data were identical to those reported for the alditol obtained from the 38-43 kDa cell-surface glycoprotein of Trypanosoma cruzi.