213591-34-5

Upstream product

• 144914-16-9 tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-dlucopyranoside 
• 1219595-38-6 tert-butyldiphenylsilyl 3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 213591-31-2 (2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6S)-4-acetoxy-2-(acetoxymethyl)-5-azido-6-((tertbutyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 213591-32-3 (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 94715-70-5 (2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R)-4-acetoxy-2-(acetoxymethyl)-5-azido-6-hydroxytetrahydro-2Hpyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 68733-14-2 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl nitrate 
• 213591-33-4 (3aS,4R,6S,7R,7aR)-6-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 

Downstream Products

• 213591-30-1 2,2,2-Trichloro-acetimidic acid (2R,3R,4R,5S,6R)-3-azido-4-benzyloxy-5-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 1219595-42-2 tert-butyldiphenylsilyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2-amino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

Solid-phase synthesis of glycopeptide carrying a tetra-N-acetyllactosamine-containing core 2 decasaccharide

A novel synthesis of tetralactosaminyl O-glycoamino acid is described. The stereoselective assemblage of a lactosaminyl unit was performed by 2-trichloroacetamido group-assisted β-glycosylation. Initial investigation into the synthesis of decasaccharyl threonine 2 showed limited success because of the low yield in the step concerning the removal of 4-O-chloroacetyl groups. In contrast, 4-O-benzylated decasaccharyl threonine 50 was efficiently synthesized from key LacNAc derivative 35 carrying a 3-O-allyl protecting group at the Gal residue by reiterative glycosylation using the (N-phenyl)trifluoroacetimidate method. Decasaccharide 50 was used as a building block in the solid-phase synthesis of a MUC1-related glycopeptide. Synthetic glycopeptide was obtained through two acidic processes: cleavage from resin with reagent K at a lowered temperature and debenzylation with a diluted cocktail of low-acidity TfOH. Desired glycopeptide 54 was isolated as the major product, while a series of the saccharide-shortened minor products were generated due to the acid-labile property of the β-GlcNAc glycosidic linkages.

Stereoselective synthesis of benzyl-protected β-galactosides by propionitrile-mediated glycosylation

β-Selective galactosylation was studied using a series of 2-O-benzylated phenyl 1-thio-galactosides and glycosyl acceptors in propionitrile with BSP-TTBP-Tf2O. The glycosylation enabled us to synthesize useful precursors of N-acetyllactosamine

Synthesis of Neolacto ganglioside LM1

The synthesis of the ganglioside LM1 (1) has been performed by glycosidation of 2 with azidosphingosine 3, followed by reduction of the azido group, acylation with stearine anhydride (4), and solvolysis. 2 was obtained from sialyl xanthate 5 and tetrasacc