53167-37-6

Upstream product

• 36954-63-9 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-deoxy-2-acetamido-1,3,4-tri-O-acetyl-α-D-glucopyranose 
• 33639-73-5 benzyl 2-acetamido-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 81243-74-5 benzyl 3,6-di-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 87190-71-4 O-<(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl>trichloracetimidat 
• 100-51-6 benzyl alcohol 
• 53167-36-5 2-methyl{3,6-di-O-acetyl-1,2-dideoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyrano}[2,1-d]oxazoline 
• 62398-01-0 2-acetamido-3,6-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranosyl chloride 

Downstream Products

• 53167-38-7 Benzyl-β-D-N-acetyllactosamine 
• 212198-25-9 C₄₃H₆₀Cl₃NO₁₈ 
• 212198-12-4 C₃₉H₅₆Cl₃NO₁₆ 
• 212198-13-5 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-3,5-diacetoxy-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 212198-11-3 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-[(2S,3R,4S,5S,6R)-4-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-3,5-dihydroxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester 

Relevant academic research and scientific papers

Chemoenzymatic Synthesis of Sialyl Sulfo-Oligosaccharides as Potent Siglec-8 Ligands via Transglycosylation Catalyzed by Keratanase II

Sialyl type-II sulfo-oligosaccharides are gaining much attention as bioactive ligands for Siglecs. In this study, we have achieved the first synthesis of sialyl type-II sulfo-oligosaccharides chemoenzymatically by utilizing the transglycosylation activity of keratanase II. The oxazoline derivative of α(2→3)-sialylated 6,6′-di-sulfo-LacNAc (3) was newly designed as the glycosyl donor for enzymatic transglycosylation. Keratanase II efficiently catalyzed the transglycosylation of 3 with two kinds of glycosyl acceptors, 6-sulfo-Lewis X and 6,6′-di-sulfo-LacNAc derivatives, providing sialyl sulfo-hexasaccharide (1) and sialyl sulfo-pentasaccharide (2) with 86 and 95% yields, respectively. The products 1 and 2 showed higher affinity to Siglec-8 with KD 70 and 25 μmol·L-1, respectively, compared to the known ligand of the α(2→3)-sialylated 6,6′-di-sulfo-Lewis X with KD 185 μmol·L-1. Thus, this study will advance not only the study of Siglec-8 biology but also the exploration of functions of sialyl sulfo-oligosaccharides having various microstructures.

Novel synthetic approaches to manβ1-4GLCNAc and LeX units from N-acetyllactosamine

Regioselective protection of N-acetyllactosamine with triphenylmethyl (trityl) and pivaloyl groups afforded the corresponding 3, 2′, 4′-tri- and 2′,4′-dihydroxyl derivatives in a few steps, respectively; these derivatives were used efficiently for the syntheses of the title compounds from N-acetyllactosamine in 46% (7 steps) and 19% (8 steps) overall yields, respectively.

SYNTHESIS OF 1,2-trans-DISACCHARIDES via SUGAR THIO-ORTHOESTERS

The reaction of sugar 1,2-thio-orthoesters in the D-gluco, D-galacto, D-manno, and L-rhamno series with primary and secondary trityl ethers of monosaccharides, in the presence of triphenylmethylium perchlorate as catalyst, affords, stereospecifically, derivatives of 1,2-trans-disaccharides in good yields. 4-Trityl ethers of benzyl 2-acetamido-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranoside and methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside exhibit low reactivity in glycosylation by thio-ortho-esters.A reaction scheme for the glycosylation is discussed.