246513-05-3

Upstream product

• 98-88-4 benzoyl chloride 
• 195316-81-5 phenyl 6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 246513-15-5 O-(2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-D-glucopyranosyl azide 
• 1204700-81-1 6-N-(2,2,2-trichloroethoxycarbonyl)aminohexyl 2,3,4-tri-O-benzoyl-O-(tert-butyldiphenylsilyl)-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 
• 195316-86-0 (2R,3aS,4R,6R,7R,7aS)-7-Benzoyloxy-4-benzoyloxymethyl-2-methyl-6-((2R,3S,4S,5R,6S)-3,4,5-tris-benzoyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-carboxylic acid methyl ester 
• 195317-02-3 (2R,3aS,4R,6R,7R,7aS)-7-Benzoyloxy-4-benzoyloxymethyl-2-methyl-6-((2R,3S,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-bromo-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-carboxylic acid methyl ester 
• 139608-11-0 phenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of a hexasaccharide that relates to the arabinogalactan epitope

A hexasaccharide derivative of the arabinogalactan epitope, methyl β-D-galactopyranosyl-(1 → 6)-[α-L-arabinofuranosyl-(1 → 3)]-β-D-galactopyranosyl-(1 → 6)-β-D-galactopyranosyl-(1 → 6)-[α-L-arabinofuranosyl-(1 → 3)]-α-D-galactopyranoside, was synthesized efficiently using a 3 + 3 strategy. The key step is the preparation of the trisaccharide donor, isopropyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1 → 6)-[2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1 → 3)]-2,4-di-O-benzoyl-1-thio-β-D-galactopyranoside, from isopropyl 1-thio-β-D-galactopyranoside using a one-pot synthesis of a 3,6-differentially protected building block.

Regiospecific syntheses of N-acetyllactosamine derivatives and application toward a highly practical synthesis of Lewis X trisaccharide

An efficient methodology for regiospecific glycosylation was developed by using 6-O-tert-butyldiphenylsilyl N-acetylglucosamine derivatives 3 and 5 which bear two free hydroxyl groups as acceptors. The regiospecificity was attributed to the presence of the tert-butyldiphenylsilyl group at the O-6 position of the N-acetylglucosamine derivatives. Glycosylation of suitably protected galactoside donors 10-14 with acceptors 3 and 5 gave only β(1→4) linked disaccharides 15-19 in good yields. Fucosylation of disaccharide 18 led to Lewis X (Lex) trisaccharide 21 in high yield.