87357-66-2

Basic information

• Product Name: Tetradecanoic acid, 3-(phenylmethoxy)-, 2-oxo-2-phenylethyl ester, (R)-
• CAS NO: 87357-66-2
• Molecular Formula: C29H40O4
• Molecular Weight: 452.634
• Mol File: 87357-66-2.mol

Chemical Properties

• CAS DataBase Reference: Tetradecanoic acid, 3-(phenylmethoxy)-, 2-oxo-2-phenylethyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Tetradecanoic acid, 3-(phenylmethoxy)-, 2-oxo-2-phenylethyl ester, (R)-(87357-66-2)
• EPA Substance Registry System: Tetradecanoic acid, 3-(phenylmethoxy)-, 2-oxo-2-phenylethyl ester, (R)-(87357-66-2)

Safety Data

• Hazardous Substances Data: 87357-66-2(Hazardous Substances Data)

Upstream product

• 87357-65-1 (3R)-3-hydroxytetradecanoic acid phenacyl ester 
• 151763-75-6 (R)-3-hydroxytetradecanoic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 70-11-1 α-bromoacetophenone 
• 28715-21-1 (R)-3-hydroxytetradecanoic acid 

Downstream Products

• 88862-41-3 C₇₁H₁₀₆N₂O₁₅ 
• 87357-75-3 (R)-3-Benzyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-5-acetylamino-2-((2R,3R,4R,5S,6R)-3-acetylamino-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-6-allyloxy-4-((R)-3-benzyloxy-tetradecanoyloxy)-tetrahydro-pyran-3-yl ester 
• 87357-69-5 (R)-3-Benzyloxy-tetradecanoic acid {(4aR,6R,7R,8R,8aS)-6-[(2R,3S,4R,5R,6R)-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy]-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-amide 
• 92454-90-5 (R)-3-Benzyloxy-tetradecanoic acid {(2R,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy]-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-amide 
• 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 
• 92949-56-9 allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside 
• 114360-80-4 allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside 
• 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 
• 87357-67-3 (R)-3-benzyloxytetradecanoic acid 

Relevant articles and documents

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.

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

Chemical Synthesis of a Biosynthetic Precursor of Lipid A with a Phosphorylated Tetraacyl Disaccharide Structure

2,2'-N:3,3'-O-Tetrakis-β(1-6)-D-glucosamine disaccharide 1,4'-bis(phosphate) and its dephospho derivatives were synthesized.The bisphosphate prepared was shown to be identical with a natural biosynthetic precursor of lipid A which corresponds to the lipophilic part of lipopolysaccharide (LPS) in bacterial cell wall.The synthetic bis- and monophosphates exhibited many of typical endotoxic activities of LPS.Consequently, this work established the chemical structure of the biosynthetic precursor of lipid A and elucidated the fundamental structure required for the expression of these activities.

SYNTHETIC APPROACH TO LIPID A: PREPARATION OF PHOSPHORYLATED DISACCHARIDES CONTAINING (R)-3-HYDROXYACYL GROUPS

A synthetic route was established to construct the proposed structure of lipid A which consists of β(1-6) glucosamine disaccharide 1,4'-diphosphate O,N-acylated with (R)-3-hydroxy- or (R)-3-acyloxytetraadecanoic acid.