201737-04-4

Upstream product

• 89116-07-4 6-benzyloxycarbonylaminohexyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 17996-12-2 N-benzyloxycarbonyl-6-amino-1-hexanol 
• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 

Downstream Products

• 201737-15-7 6-benzyloxycarbonylaminohexyl 2,3,4-tri-O-benzoyl-6-O-triphenylmethyl-β-D-galactopyranoside 
• 201737-16-8 6-benzyloxycarbonylaminohexyl 2,3,4-tri-O-benzoyl-β-D-galactopyranoside 
• 201737-12-4 6-benzyloxycarbonylaminohexyl 2-O-acetyl-3-O-benzoyl-6-O-benzyl-β-D-galactopyranoside 
• 201737-11-3 Benzoic acid (4aR,6R,7R,8S,8aS)-7-acetoxy-6-(6-benzyloxycarbonylamino-hexyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 201737-10-2 6-benzyloxycarbonylaminohexyl 3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 571201-34-8 Benzyl-[6-((4aR,6R,7R,8S,8aS)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-hexyl]-carbamic acid benzyl ester 
• 201737-05-5 6-benzyloxycarbonylaminohexyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 201737-14-6 [6-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-hexyl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

First intramolecular aglycon delivery onto a D-fucofuranosyl entity for the synthesis of α-D-fucofuranose-containing disaccharides

Intramolecular aglycon delivery was performed for the first time starting from n-pentenyl glycofuranoside as a donor. p-Methoxybenzyl-assisted aglycon transfer required very mild reaction conditions and was promoted by N-iodosuccinimide without assistance of any Lewis acid catalyst. As a result, rare α-D-fucofuranose-containing disaccharides were obtained. Moreover, structure elucidation led to the conclusion that an N-succinimidyl residue was still present in the resulting products. Wiley-VCH Verlag GmbH & Co, KGaA, 69451 Weinheim, Germany, 2003.

Synthesis of a set of highly clustered monosulfated galactopyranosides

There are several biological events that are known to involve certain sulfated saccharides. In many such cases, however, clustered ligands have been shown to be more effective than monovalent saccharides. A set of 6-aminohexyl glycosides of 2,3,4 or 6-monosulfated galactose have been synthesized and linked to polyglutamic acid. Because of the bulky aglycon employed, the 2-OH group of the key compound, 6-benzyloxycarbonylaminohexyl 4,6-O-benzylidene-β-D-galactopyranosid was markedly less reactive than 3-OH. Thus, site-specific acetylation of 3-OH was readily carried out to obtain 2-O-sulfated galactosides, and even the direct sulfation of 3-OH afforded the 3-sulfate in a reasonable yield. On the other hand, the key compound was unexpectedly resistant to 2,3-O-dibenzylation or 2,3-O-dibenzoylation, both of which were meant for regioselective cleavage of 4,6-benzylidene to obtain the 4-sulfate.