91681-56-0

Usage

InChI:InChI=1/C26H50O4/c1-3-5-7-9-11-13-15-17-19-21-24(23-25(27)28)30-26(29)22-20-18-16-14-12-10-8-6-4-2/h24H,3-23H2,1-2H3,(H,27,28)/t24-/m1/s1

Upstream product

• 151763-75-6 (R)-3-hydroxytetradecanoic acid ethyl ester 
• 28715-21-1 (R)-3-hydroxytetradecanoic acid 
• 87357-65-1 (3R)-3-hydroxytetradecanoic acid phenacyl ester 
• 339316-63-1 (R)-3-Dodecanoyloxy-tetradecanoic acid 2-oxo-2-phenyl-ethyl ester 
• 79816-65-2 tert-butyl (R)-3-hydroxytetradecanoate 
• 163562-85-4 tert-butyl (2S, 3R)-2,3-dihydroxytetradecanoate 
• 321581-82-2 tert-butyl 2-tetradecenoate 
• 112-54-9 Dodecanal 
• 163562-89-8 tert-butyl (R)-3-dodecanoyloxytetradecanoate 
• 186383-49-3 2-(4-bromophenyl)-2-oxoethyl (R)-3-hydroxytetradecanoate 
• 22348-97-6 methyl 3-oxotetradecanoate 
• 76062-97-0 methyl (R)-3-hydroxytetradecanoate 
• 112-16-3 n-dodecanoyl chloride 
• 143-07-7 lauric acid 

Downstream Products

• 3651-67-0 N-methylmorpholine hydrochloride 
• 937394-29-1 tert-butyldimethylsilyl 6-O-{3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-[(R)-3-dodecanoyloxy-tetradecanoylamino]-β-D-glucopyranosyl}-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 216013-89-7 N-[(R)-3-dodecanoyloxytetradecanoyl]-L-serine benzyl ester 
• 216013-29-5 3-benzyloxy-(S)-2-(allyloxycarbonylamino)propyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-dodecanoyloxytetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 
• 525604-35-7 N-[(R)-3-dodecanoyloxytetradecanoyl]-O-[2-deoxy-4-O-diphenylphosphono-2-[(R)-3-dodecanoyloxytetradecanoylamino]-3-O-[(R)-3-dodecanoyloxytetradecanoyl]-β-D-glucopyranosyl]-L-serine benzyl ester 
• 253586-92-4 N-[(R)-3-dodecanoyloxytetradecanoyl] O-bis(phenyloxy)phosphoryl DL-homoserine benzyl ester 
• 216013-30-8 3-benzyloxy-(S)-2-[(R)-3-dodecanoyloxytetradecanoylamino]propyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-dodecanoyloxytetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 
• 1194397-69-7 2-azidoethyl 4,6-O-benzylidene-2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanamido]-β-D-glucopyranosyl-(1→6)-4-O-benzyl-2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanamido]-β-D-glucopyranoside 
• 1218992-56-3 C₁₄₃H₂₂₂N₃O₂₃P 
• 1025449-65-3 allyl-3,4-di-O-benzyl-6-O-{3,6-di-O-benzyl-4-O-(dibenzyloxyphosphoryl)-2-deoxy-2-[(R)-3-dodecanoyloxytetradecanoylamino]-β-D-glucopyranosyl}-2-[(R)-3-benzyloxytetradecanoylamino]-2-deoxy-α-D-glucopyranoside 
• 1214268-30-0 C₁₂₁H₂₀₇N₂O₂₅PSi 
• 1214268-24-2 C₁₁₄H₁₉₁N₂O₂₅P 

Relevant academic research and scientific papers

BIFUNCTIONAL COMPOUND AND ITS USE IN IMMUNOTHERAPY

The invention relates to a bifunctional compound that is, on one side, an agonist of the TLR4 and, on the other side, an important inhibitor of the PSMA. Said compound is useful in immunotherapy for the treatment and/or prevention of prostate cancer. Therefore, the invention also relates to the use of the compound and to the pharmaceutical composition comprising it.

Synthesis of monophosphoryl lipid A using 2-naphtylmethyl ethers as permanent protecting groups

Lipid A, which is a conserved component of lipopolysaccharides of gram-negative bacteria, has attracted considerable interest for the development of immuno-adjuvants. Most approaches for lipid A synthesis rely on the use of benzyl ethers as permanent protecting groups. Due to the amphiphilic character of lipid A, these compounds aggregate during the hydrogenation step to remove benzyl ethers, resulting in a sluggish reaction and by-product formation. To address this problem, we have developed a synthetic approach based on the use of 2-naphtylmethyl ether (Nap) ethers as permanent protecting group for hydroxyls. At the end of a synthetic sequence, multiple of these protecting groups can readily be removed by oxidation with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ). Di-allyl N,N-diisopropylphosphoramidite was employed to install the phosphate ester and the resulting allyl esters were cleaved using palladium tetrakistriphenylphosphine. The synthetic strategy allows late stage introduction of different fatty acids at the amines of the target compound, which is facilitated by Troc and Fmoc as orthogonal amino-protecting groups.

One-Pot Protection Strategy of Glucosamine to Assemble Building Blocks of Chitosan and Lipid A

This investigation describes a one-pot reaction to prepare a series of building blocks for glycosylation reactions, such as 3-alcohol glucosamines, fully protected glucosamines, O-4 and O-6 alcohol glucosamines. These reactions readily produce not only gl

SYNTHETIC DERIVATIVES OF MPL AND USES THEREOF

In one aspect, the present disclosure provides compounds of formulae (I) and (II). In another aspect, a compound of formula (I) or (II) is formulated into compositions with an antigen, optionally with a vesicle. In some embodiments, compositions are administered intramuscularly.

Aminoalkyl glucosaminide phosphate compounds and their use as adjuvants and immunoeffectors

Aminoalkyl glucosaminide phosphate (AGP) compounds that are adjuvants and immunoeffectors are described and claimed. The compounds have a 2-deoxy-2-amino glucose in glycosidic linkage with an aminoalkyl (aglycon) group. Compounds are phosphorylated at the 4 or 6 carbon on the glucosaminide ring and comprise three 3-alkanoyloxyalkanoyl residues. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Compositions and methods for using the compounds as adjuvants and immunoeffectors are also disclosed.

Aminoalkyl glucosaminide phosphate compounds and their use as adjuvants and immunoeffectors

Aminoalkyl glucosaminide phosphate (AGP) compounds that are adjuvants and immunoeffectors are described and claimed. The compounds have a 2-deoxy-2-amino glucose in glycosidic linkage with an aminoalkyl (aglycon) group. Compounds are phosphorylated at the 4 or 6 carbon on the glucosaminide ring and comprise three 3- alkanoyloxyalkanoyl residues. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Compositions and methods for using the compounds as adjuvants and immunoeffectors are also disclosed.

Aminoalkyl glucosaminide phosphate compounds and their use as adjuvants and immunoeffectors

Aminoalkyl glucosaminide phosphate (AGP) compounds that are adjuvants and immunoeffectors are described and claimed. The compounds have a 2-deoxy-2-amino glucose in glycosidic linkage with an aminoalkyl (aglycon) group. Compounds are phosphorylated at the 4 or 6 carbon on the glucosaminide ring and comprise three 3-alkanoyloxyalkanoyl residues. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Methods for using the compounds as adjuvants and immunoeffectors are also disclosed.

Aminoalkyl glucosamine phosphate compounds and their use as adjuvants and immunoeffectors

Aminoalkyl glucosamine phosphate compounds that are adjuvants and immunoeffectors are described and claimed. The compounds have a 2-deoxy-2-amino glucose in glycosidic linkage with an aminoalkyl (aglycon) group. Compounds are phosphorylated at the 4 or 6 carbon on the glucosamine ring and comprise three 3-alkanoyloxyalkanoyl residues. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Methods for using the compounds as adjuvants and immunoeffectors are also disclosed.

Lipid-A analogs: monosaccharide and dissaccharide compounds for inhibiting binding of lipid A receptors to lipid A receptors

A compound of the formula: STR1 wherein: each of R1, R1 ', R2 and R2 ' independent of each other is a substituted or unsubstituted, branched or linear C1-12 alkyl, alkene or alkyne group, R3/sub

Lipid-A analogs: new monosaccharide and disaccharide intermediates for eliciting therapeutic antibodies and for antitumor and antiviral activities

The present invention relates to novel amidine components of formula (II): STR1 A method for eliciting antibodies in an animal which bind to Lipid A or LPS comprising administering to the animal as an immunogen a composition comprising such a compound is