87357-67-3

Usage

Chemical Properties

Light Yellow Liquid

InChI:InChI=1/C21H34O3/c1-2-3-4-5-6-7-8-9-13-16-20(17-21(22)23)24-18-19-14-11-10-12-15-19/h10-12,14-15,20H,2-9,13,16-18H2,1H3,(H,22,23)/t20-/m1/s1

Upstream product

• 87357-66-2 phrnacyl (R)-3-(benzyloxy)tetradecanoate 
• 114264-01-6 methyl (R)-3-(benzyloxy)tetradecanoate 
• 143152-69-6 tert-butyl (R)-3-benzyloxytetradecanoate 
• 76062-97-0 methyl (R)-3-hydroxytetradecanoate 
• 186383-49-3 2-(4-bromophenyl)-2-oxoethyl (R)-3-hydroxytetradecanoate 
• 100-52-7 benzaldehyde 
• 139623-16-8 (R)-3-benzyloxy-1-hydroxytetradecane 
• 112-54-9 Dodecanal 
• 335153-25-8 (E)-Tetradec-2-enoic acid ethyl ester 
• 22348-97-6 methyl 3-oxotetradecanoate 
• 143-07-7 lauric acid 
• 151763-75-6 (R)-3-hydroxytetradecanoic acid ethyl ester 
• 100-39-0 benzyl bromide 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 

Downstream Products

• 101649-06-3 N-((R)-3-Benzyloxytetradecanoyloxy)succinimid 
• 118638-71-4 2-acetoxyethyl 3,4,6-tri-O-acetyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-α-D-glucopyranoside 
• 87357-71-9 C₁₂₇H₁₉₄N₂O₁₉ 
• 93390-33-1 (R)-3-Benzyloxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-allyloxy-5-benzyloxy-6-benzyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester 
• 98870-61-2 (R)-3-Benzyloxy-tetradecanoic acid (4aR,6S,7R,8R,8aS)-6-allyloxy-7-((R)-3-benzyloxy-tetradecanoylamino)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 88862-41-3 C₇₁H₁₀₆N₂O₁₅ 
• 92949-55-8 allyl 6-O-<3,4,6-tri-O-acetyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranoside 
• 87357-70-8 C₁₀₉H₁₆₆N₂O₁₇ 
• 92949-57-0 C₁₀₉H₁₆₆N₂O₁₇ 
• 88862-42-4 C₈₉H₁₃₄N₂O₁₇ 
• 87357-68-4 Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-2-yloxymethyl]-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester 
• 135561-36-3 benzyl <2-<(R)-3-(benzyloxy)tetradecanamido>-2-deoxy-3,4-O-bis<(R)-3-(benzyloxy)tetradecanoyl>-6-O-(triphenylmethyl)-α-D-glucopyranosyl>acetate 
• 135561-30-7 benzyl <4,6-O-benzylidene-2-<(R)-3-(benzyloxy)tetradecanamido>-3-O-<(R)-3-(benzyloxy)tetradecanoyl>-2-deoxy-α-D-glucopyranosyl>acetate 
• 135561-60-3 benzyl <2-acetamido-4,6-O-benzylidene-3-O-<(R)-3-(benzyloxy)tetradecanoyl>-2-deoxy-α-D-glucopyranosyl>acetate 

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.

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

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.

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.

Preparation of a lipid A derivative that contains a 27-hydroxyoctacosanoic acid moiety

(Chemical Equation Presented) A general synthetic strategy for long-chain ω-1 hydroxy fatty acids has been developed, which employs as a key reaction step a cross metathesis between ω-unsaturated ester and 3-butene-2-ol. The resulting lipids were used for

Divergent synthesis and biological activities of lipid A analogues of shorter acyl chains

Novel lipid A analogues which possess four (R)-3-hydroxyacyl moieties of shorter chain length were synthesized via new divergent synthetic route in order to clarify the effect of the chain length of acyl groups to the biological activity: a disaccharide 4

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

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

On a Practical Synthesis of β-Hydroxy Fatty Acid Derivatives

An efficient synthesis of three homochiral β-hydroxy fatty acid derivatives, which have been utilized in our total synthesis of lipid A, is reported.The synthesis features Sharpless asymmetric dihydroxylation of an unsaturated ester, regioselective conversion of a diol into acyloxy chlorides, and a reductive removal of the chloro group.

Production of oxetanones

The invention relates to a novel process for producing a compound having the formula STR1 wherein R1, R2 and X are described herein, via wherein R corresponding β-keto- and β-hydroxy-δ-lactones, as well as novel intermediates which occur in the process.