88862-84-4

Upstream product

• 28715-21-1 (R)-3-hydroxytetradecanoic acid 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 112-54-9 Dodecanal 
• 76062-97-0 methyl (R)-3-hydroxytetradecanoate 
• 51758-20-4 4-undecyloxetan-2-one 
• 100-51-6 benzyl alcohol 

Downstream Products

• 914499-86-8 benzyl (R)-3-dodecanoyloxytetradecanoate 
• 346669-98-5 N-[(R)-3-dodecanoyloxytetradecanoyl]-L-aspartic acid β-benzyl ester 
• 346669-80-5 N-[(R)-3-dodecanoyloxytetradecanoyl]-D-aspartic acid β-benzyl ester 
• 253587-43-8 O-bis(phenyloxy)phosphoryl N-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine 
• 253586-92-4 N-[(R)-3-dodecanoyloxytetradecanoyl] O-bis(phenyloxy)phosphoryl DL-homoserine benzyl ester 
• 346670-00-6 N-[(R)-3-dodecanoyloxytetradecanoyl]-L-homoserine α-N-{(4R)-5-(benzyloxymethoxy)-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 
• 253587-01-8 O-bis(phenyloxy)phosphoryl Nα-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine N-{(4R)-5-hydroxy-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide 
• 346669-97-4 N-[(R)-3-dodecanoyloxytetradecanoyl]-L-aspartic acid α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide β-benzyl ester 
• 118638-59-8 1-O-acetyl-2-deoxy-4-O-diphenylphosphono-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-3-O-<(R)-3-(2,2,2-trichloroethoxycarbonyloxy)tetradecanoyl>-D-glucopyranose 
• 137600-37-4 allyl 2-deoxy-4-O-diphenylphosphono-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-3-O-<(R)-3-(2,2,2-trichloroethoxycarbonyloxy)tetradecanoyl>-α-D-glucopyranoside 
• 137600-40-9 (R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid (2R,3R,4R,5S,6R)-2-bromo-5-(diphenoxy-phosphoryloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-6-(2,2,2-trichloro-ethoxycarbonyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 85065-41-4 benzyl 2-<(3R)-3-acetoxytetradecanamido>-6-O-<2-<(3R)-3-acetoxytetradecanamido>-3-O-acetyl-6-O-benzyloxymethyl-2-deoxy-β-D-glucopyranosyl>-3,4-di-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 85065-39-0 benzyl 2-<(3R)-3-acetoxytetradecanamido>-6-O-<2-<(3R)-3-acetoxytetradecanamido>-3-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl>-3,4-di-O-acetyl-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

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.

Lipase promoted asymmetric trans-esterification of 4-alkyl-, 3-alkyl- and 3,4-dialkyloxetan-2-ones with ring-opening

Kinetic resolution of(+/-)-4-substituted [(+/-)-1], 3-substituted [(+/-)-4] and 3,4-disubstituted oxetan-2-ones [(+/-)-7] was effected by the action of lipases in organic solvents. The substrates (+/-)-1, (+/-)-4 and (+/-)-7 were prepared by [2 + 2] cycloaddition of aldehydes with ketene, intramolecular substitution of 3-bromoalkanoic acids and the Adam's cyclization of anti- and syn-3-hydroxyalkanoic acids, respectively. Lipase PS exhibited good activity towards all the oxetanones and was employed for the resolution experiments except with (+/-)-4-methyloxetan-2-one (+/-)-1a for which PPL was used. The stereoselectivity was satisfactory for obtaining oxetan-2-ones of high ee's except for a few cases. The configuration of new compounds was established by chemical correlation and CD spectroscopy.

Synthesis and biological activities of analogs of a lipid A biosynthetic precursor: 1-O-phosphono-oxyethyl-4'-O-phosphono-disaccharides with (R)-3-hydroxytetradecanoyl or tetradecanoyl groups at positions 2, 3, 2' and 3'

Two novel analogs of a biosynthetic precursor of lipid A (2) were synthesized. The one analog (3) has acyl groups identical to those of 2, and the other (4) has tetradecanoyl groups in place of the (R)-3-hydroxytetradecanoyl groups of 2. Both 3 and 4 poss

Chemistry of Bacterial Endotoxins. Part 2. A Practical Synthesis of 6-O--β-D-glucopyranosyl>-2-deoxy-2--D-glucose

An improved method for the preparation of the phosphorylated disaccharide named in the title, via benzyl 2-amino-6-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside, is described.