114264-01-6

Usage

Chemical Properties

Colourless Oil

InChI:InChI=1/C22H36O3/c1-3-4-5-6-7-8-9-10-14-17-21(18-22(23)24-2)25-19-20-15-12-11-13-16-20/h11-13,15-16,21H,3-10,14,17-19H2,1-2H3/t21-/m1/s1

Upstream product

• 76062-97-0 methyl (R)-3-hydroxytetradecanoate 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 
• 28715-21-1 (R)-3-hydroxytetradecanoic acid 
• 143-07-7 lauric acid 
• 22348-97-6 methyl 3-oxotetradecanoate 
• 74794-26-6 (3R)-1-trimethylsilyl-tetradec-1-yn-3-ol 
• 73501-40-3 tetradec-1-yn-3-one 
• 77889-04-4 (R)-(-)-1-tetradecyn-3-ol 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 

Downstream Products

• 125638-37-1 (3R,4S)-3-hexyl-4-<(R)-2'-(benzyloxy)tridecyl>-2-oxetanone 
• 125638-36-0 (3R,4R)-4-((R)-2-Benzyloxy-tridecyl)-3-hexyl-oxetan-2-one 
• 125638-38-2 (3S,4R)-4-((R)-2-Benzyloxy-tridecyl)-3-hexyl-oxetan-2-one 
• 125564-93-4 3-hexyl-3-trimethylsilyl-4-<(R)-2'-(benzyloxy)tridecyl>-2-oxetanone 
• 114264-04-9 (1R,2S)-2-(dimethylamino)-1-phenylpropyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate 
• 114299-20-6 (2S,3S,5R)-5-(benzyloxy)-3-hydroxy-2-hexylhexadecanoic acid 
• 114264-05-0 (3S,4S)-4-((R)-2(benzyloxy)tridecyl)-3-hexyl-2-oxetanone 
• 68711-40-0 (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone 
• 104872-04-0 Orlistat 
• 346669-97-4 N-[(R)-3-dodecanoyloxytetradecanoyl]-L-aspartic acid α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide β-benzyl ester 
• 253587-01-8 O-bis(phenyloxy)phosphoryl Nα-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine N-{(4R)-5-hydroxy-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide 
• 253586-99-1 O-bis(phenyloxy)phosphoryl N-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine N-{(4R)-5-hydroxy-4-[(R)-3-hydroxytetradecanoylamino]pentyl}amide 
• 346670-00-6 N-[(R)-3-dodecanoyloxytetradecanoyl]-L-homoserine α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide 
• 346669-95-2 (2R)-5-(benzyloxycarbonylamino)-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol benzyloxymethyl ether 

Relevant academic research and scientific papers

SYNTHETIC GLUCOPYRANOSYL LIPID ADJUVANTS

PROBLEM TO BE SOLVED: To provide a novel glucopyranosyl lipid adjuvant (GLA) for inducing or enhancing immune responses, and a vaccine composition and a pharmaceutical composition comprising the GLA. SOLUTION: The present invention provides a GLA represented by a compound of the following formula, and a vaccine composition and a pharmaceutical composition comprising the GLA. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Synthesis and immunobiological activity of an original series of acyclic lipid A mimics based on a pseudodipeptide backbone

Nδ-L-Homoserinyl-D-ornithinol pseudodipeptides N-acylated with typical Escherichia coli lipid A fatty acid residues and mono-O- or bis-O-phosphorylated have been prepared and their properties investigated. The derivatives carrying two phosphate groups were found to be inducers of NO production. In addition, while they were unable to induce significantly the production of interleukin-6 (IL-6) by human PBMC cells, these compounds behaved also as potent antagonists of LPS-induced IL-6 production in the same human cells system. In conclusion, the molecules described here are the first members of an original class of immunobiologically active lipid A mimics based on an acyclic pseudodipeptide backbone carrying only the essential functionalities of the parent lipid A structure (OM-174). As the products exhibit very low endotoxicity and pyrogenicity, this class of lipid A mimics therefore opens a new generation of immunoadjuvants that possibly could reach clinical applications.

CHEMISTRY OF BACTERIAL ENDOTOXINS. PART 3. REACTIONS OF OXAZOLINES DERIVED FROM 1,3,4,6-TETRA-O-ACETYL-2-Β-D-GLUCOPYRANOSE

In acidic medium the oxazoline derived from 2--1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose readily eliminates elements of acetic acid: it is transformed into an oxazoline that carries an olefinic substituent having the E configuration; this compound, when treated with an alcohol, yields the corresponding β-D-glucosaminide.No elimination takes place with the analogous 3-hydroxy- or 3-benzyloxy-tetradecanamidoglucosamine derivatives. (3R)-3-benzyloxy-tetradecanoic acid was obtained in 60percent yield upon treatment of methyl (3R)-3-hydroxytetradecanoate in benzene with benzyl bromide, silver oxide, and anhydrous calcium sulphate, followed by saponification.Under similar conditions 3,4,6-tri-O-acetyl-1,2-dideoxy-4',5'-dihydro-2--α-D-glucopyranosooxazole was transformed into the corresponding (2R)-2-benzyloxyoxazoline.