81243-72-3

Upstream product

• 68733-24-4 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl bromide 
• 100-51-6 benzyl alcohol 

Downstream Products

• 17048-95-2 α-D-NANA-(2->6)-β-D-Gal(1->4)-D-GlcNAc 
• 17048-95-2 β-D-NANA-(2->)-β-D-Gal(1->4)-D-GlcNAc 
• 53167-39-8 benzyl 2-amino-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside 
• 89733-60-8 Benzyl-O-(methyl-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onat)-(2->6)-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-amino-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid-Dihydrogensulfid 
• 89733-61-9 Benzyl-O-(methyl-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onat)-(2->6)-O-(4-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid 
• 89733-62-0 Benzyl-O-(5-acetamido-3,5-didesoxy-D-glycero-α-D-galacto-2-nonulopyranosylonsaeure)-(2->6)-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid 
• 89748-02-7 Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(2,3-di-O-benzyl-4,6-O-benzyliden-β-D-galactopyranosyl)-β-D-glucopyranosid 
• 85750-97-6 Benzyl-2-azido-3,6-di-O-benzyl-2-desoxy-4-O-(2,3-di-O-benzyl-4,6-O-benzyliden-β-D-galactopyranosyl)-β-D-glucopyranosid 
• 85750-98-7 Benzyl-2-azido-3,6-di-O-benzyl-2-desoxy-4-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranosid 
• 85750-96-5 Benzyl-2-azido-4-O-(4,6-O-benzyliden-β-D-galactopyranosyl)-2-desoxy-β-D-glucopyranosid 
• 81243-73-4 benzyl 2-azido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

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.

SYNTHESE EINES TRISACCHARIDES AUS N-ACETYLNEURAMINSAEURE UND N-ACETYLLACTOSAMIN

The reaction of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-D-glycero-β-D-galacto-2-nonulopyranosonate with benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside in the presence of mercury cyanide-mercuri bromide gave a 1:1 mixture of the two anomeric (2->6)linked trisaccharides containing N-acetylneuraminic acid.By chromatography, 22percent of benzyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->6)-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside and 23percent of the corresponding β-(2->6)-linked isomer could be isolated.A deblocking sequence, consisting of hydrogen sulfide reduction, acetylation, deacetylation, ester hydrolysis and hydrogenolysis led to the deblocked O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-O-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-D-glucopyranose and to the corresponding β-(2->6)-linked compound.