158938-08-0

Basic information

• Product Name: [1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-
• Synonyms: [1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-;4-(4''-pentyloxy-1,1':4',1''-terphenyl)-carboxylic acid;4''-(pentyloxy)-[1,1':4',1''-Terphenyl]-4-carboxylic acid
• CAS NO: 158938-08-0
• Molecular Formula: C₂₄H₂₄O₃
• Molecular Weight: 360.45
• EINECS: 691-410-4
• Mol File: 158938-08-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 557.9±43.0 °C(Predicted)
• Appearance: /
• Density: 1.117
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.23±0.10(Predicted)
• CAS DataBase Reference: [1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: [1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-(158938-08-0)
• EPA Substance Registry System: [1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-(158938-08-0)

Safety Data

• Hazardous Substances Data: 158938-08-0(Hazardous Substances Data)

Usage

Chemical Properties

off-white solid

Uses

4''''-(Pentyloxy)-[1,1'':4'',1''''-terphenyl]-4-carboxylic Acid is an intermediate used in the synthesis of Anidulafungin (A673000) which is a semisynthetic echinocandin that inhibits glucan synthase, an enzyme important in the formation of (1→3)-β-D-glucan, a major fungal cell wall component, and thus is used as antifungal drug.

Upstream product

• 14047-29-1 4-carboxyphenylboronic acid 
• 63619-51-2 4-bromo-4'-pentyloxybiphenyl 
• 5731-12-4 4’-iodo-[1,1’-biphenyl]-4-carboxylic acid 
• 146449-90-3 [4-(pentyloxy)phenyl]boronic acid 
• 289706-68-9 4-n-pentoxyphenylboronic acid ethylene glycol ester 
• 106-37-6 1.4-dibromobenzene 
• 4612-26-4 1,4-Phenyldiboronic acid 
• 115171-02-3 4-n-pentyloxyphenylmagnesium bromide 
• 619-58-9 4-iodobenzoic acid 
• 99770-93-1 benzene-1,4-diboronic acid bispinacol ester 
• 116223-55-3 1-iodo-4- (pentyloxy) benzene 
• 30752-18-2 1-bromo-4-pentyloxybenzene 
• 586-76-5 4-Bromobenzoic acid 
• 110-53-2 1-Bromopentane 

Downstream Products

• 158937-65-6 2,4,5-trichlorophenyl 4-(4'-pentyloxybiphenyl)benzoate 
• 1334511-82-8 C₄₅H₆₀N₄O₈ 
• 1203557-57-6 C₄₄H₅₈N₄O₉ 
• 1345195-60-9 C₆₁H₇₈N₈O₁₄ 
• 1345195-46-1 C₆₁H₇₆N₈O₁₄ 
• 1345195-40-5 C₈₃H₁₁₈N₈O₁₆ 
• 166663-25-8 Anidulafungin 

Relevant articles and documents

Unified Protocol for Fe-Based Catalyzed Biaryl Cross-Couplings between Various Aryl Electrophiles and Aryl Grignard Reagents

The combination of commonly used FeCl3/SIPr with Ti(OEt)4/PhOM enabled a highly general iron-based catalyst system, which could efficiently catalyze the biaryl coupling reaction between various electrophiles (I, Br, Cl, OTs, OCONMe2, OSO2NMe2) and common or functionalized aryl Grignard reagents with high functional group tolerance. Selective couplings of aryl iodides and bromides over the corresponding oxygen-based electrophiles have been achieved, and thus a terphenyl acid intermediate for anidulafungin was conveniently synthesized via an orthogonal coupling strategy.

Preparation method of anidulafungin intermediate

The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of an anidulafungin intermediate. The preparation method includes the steps of (1), subjecting iodobenzoic acid and 1,4-indole-dibenzoboronic acid pinacol ester to reaction in a solvent in the presence of palladium and alkali; (2), adding 4-p-(pentyloxy) iodobenzene to reaction liquid of the step (1) to obtain 4''-(pentyloxy)-[1,1':4',1''-Terphenyl]-4-carboxylic acid, namely the anidulafungin intermediate. The preparation method is easy in operation and high in yield and capable ofmeeting requirements on industrial production.

Off-axis digital holographic microscope as described in any one of Claims 1 to 6, includes a light coupled to the target unit (Sa) fluorescence excitation source (17).

The invention belongs to the field of medicine synthesis and specifically relates to a preparation method of an anidulafungin side chain intermediate 4'-orthopentyloxy-1,1':4',1'-terphenyl-4-carboxylic acid. The preparation method comprises the following steps: initiating a 1,4-dibromo-benzene material which serves as a starting material to carry out Grignard reagent reaction with magnesium by iodine; then, preparing 1,4-benzene hypoboric acid by virtue of addition and hydrolysis with trimethyl borate; and preparing 4'-orthopentyloxy-1,1':4',1'- terphenyl-ethyl carboxylate by virtue of Suzuki reaction of 1,4-benzene hypoboric acid, 4-pentyloxy bromobenzene and 4-halogenated ethyl benzoate in dioxane-ethanol liquor under catalysis of [1,1'-bis(diphenyl phosphino) ferrocene] palladium dichloride, and then, hydrolyzing to obtain a target product. The preparation method disclosed by the invention can lower process cost, is simple, convenient, safe and reliable to operate, and suitable for industrial production.