81243-74-5

Upstream product

• 85-44-9 phthalic anhydride 
• 53167-39-8 benzyl 2-amino-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside 
• 76542-62-6 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-1,3,6-tri-O-acetyl-2-deoxy-2-phthalimido-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 
• 68124-18-5 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-1,3,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 

Downstream Products

• 91852-24-3 benzyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 91852-26-5 Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-6-benzyloxy-3-((2S,3R,4S,5S,6R)-3,4-diacetoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester 
• 91852-29-8 benzyl 3,6-di-O-acetyl-4-O-(2,3,4-tri-O-acetyl-6-deoxy-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 91852-28-7 benzyl 3,6-di-O-acetyl-4-O-(2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-galactopyranosyl)-2-deoxy-2-phthalimido-α-D-glucopyranoside 
• 91852-25-4 benzyl 3,6-di-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 91852-27-6 Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-6-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-methanesulfonyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 53167-37-6 benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranoside 
• 114262-29-2 benzyl 3,6-di-O-acetyl-2-deoxy-4-O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2-phthalimido-β-D-glucopyranoside 
• 114262-31-6 benzyl O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 114262-28-1 2-[(2R,3R,4R,5S,6R)-2-Benzyloxy-4-hydroxy-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 
• 91852-23-2 benzyl 4-O-(β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside 

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.

Syntheses of linear tetra-, hexa-, and octa-saccharide fragments of the i-blood group active poly-(N-acetyl-lactosamine) series. Blockwise methods for the synthesis of repetitive oligosaccharide sequences.

N-Phthaloylation of lactosamine gave various glycosyl donors (beta-chloride, beta-trichloroacetimidate) and glycosyl acceptors (3',4'-diol). Coupling of the chloride with a methyl beta-D-glycoside led to the tetrasaccharide fragment, beta-D-Galp-(1----4)-

SYNTHESIS OF AN OCTASACCHARIDE FRAGMENT OF THE POLYLACTOSAMINE SERIES BY A BLOCKWISE APPROACH

Block synthesis of an octasaccharide, β-(1-3) linked tetramer of N-acetyllactosamine, is reported.Intermediate di- and tetrasaccharides were converted either into trichloroacetimidates acting as glycosyl donors or into vicinal diols acting as glycosyl acc

Syntheses of derivatives of N-acetyl-D-lactosamine from D-lactal hexaacetate. Hexa-O-acetyl-2-deoxy-2-phthalimido-β-D-lactosyl chloride

Two reaction routes are presented for the preparation of hexa-O-acetyl-2-deoxy-2-phthalimido-β-D-lactosyl chloride (7) from lactal hexaacetate (1).One route involves, in the first stage, reaction of 1 with nitrosyl chloride and proceeds by way of benzyl 2-amino-2-deoxy-α-D-lactoside (4) as an intermediate.The other route, which is considered more efficient, involves reaction of 1 with ceric ammonium nitrate and sodium azide and involves the β-anomer (12) of 4 as an intermediate.The preparation of 7 is of interest as a reagent for the preparation of 2-amino-2-deoxy-β-D-lactosides.The procedures offer routes for the preparation of D-lactosamine.