1293922-75-4

Basic information

• Product Name: N-(9-fluorenylmethoxycarbonyl)-O-(2-O-p-methoxybenzyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl)-L-serine allyl ester
• CAS NO: 1293922-75-4
• Molecular Weight: 777.868
• Mol File: 1293922-75-4.mol

Chemical Properties

• CAS DataBase Reference: N-(9-fluorenylmethoxycarbonyl)-O-(2-O-p-methoxybenzyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl)-L-serine allyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(9-fluorenylmethoxycarbonyl)-O-(2-O-p-methoxybenzyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl)-L-serine allyl ester(1293922-75-4)
• EPA Substance Registry System: N-(9-fluorenylmethoxycarbonyl)-O-(2-O-p-methoxybenzyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl)-L-serine allyl ester(1293922-75-4)

Safety Data

• Hazardous Substances Data: 1293922-75-4(Hazardous Substances Data)

Upstream product

• 161007-96-1 (p-methylphenyl) 4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 136497-85-3 N-(9-fluorenylmethoxycarbonyl)-L-serine allyl ester 
• 1293922-69-6 S-p-tolyl 3-O-allyl-2-O-p-methoxybenzyl-4,6-O-benzylidene-β-D-thiogalactopyranoside 

Relevant articles and documents

Synthesis of serine-based glycolipids as potential TLR4 activators

A new series of monosaccharide-based glycolipids devoid of phosphate groups and with two lipid chains were rationally designed by varying the lipid chain lengths and saccharide structure of a α-GalCer-derived lead compound (CCL-34) that is a potent TLR4 agonist. The NF-κB activity of a 60-membered galactosyl serine-based synthetic library containing compounds with various lipid chain lengths was measured in a HEK293 cell line that stably expressed human TLR4, MD2, and CD14 (293-hTLR4/MD2-CD14). The results showed that the optimal carbon chain lengths for the lipid amine and fatty acid to activate TLR4 were 10-11 and 12, respectively. Evaluation of a 20-membered synthetic glycosyl serine-based lipid library containing compounds with various saccharide moieties and fixed lipid chain lengths revealed that the galactose moiety in CCL-34 could be replaced by glucose without loss of activity (CCL-34-S3 and CCL-34-S16). Changing the orientation of the anomeric glycosidic bond of CCL-34 resulted in a complete loss of activity (β-CCL34). Surprisingly, a change in configuration of the anomeric glycosidic bond in a glucosyl glycolipid is tolerable (CCL-34-S14). Another noteworthy observation is that the activity of a l-fucosyl derived glycolipid (CCL-34-S13) was comparable to that of CCL-34. In sum, this study determines the structural features that are crucial for an optimal TLR4-stimulating activity. It also provides several molecules with immunostimulating potential.