135355-96-3

Basic information

• Product Name: (E)-4-TERT-BUTOXY-4-OXOBUT-2-ENOIC ACID
• Synonyms: (E)-4-TERT-BUTOXY-4-OXOBUT-2-ENOIC ACID;Fumaric acid mono-tert-butyl ester;FuMaric Acid tert-Butyl Ester
• CAS NO: 135355-96-3
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.17848
• Product Categories: Aliphatics, Metabolites & Impruities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 135355-96-3.mol

Chemical Properties

• Melting Point: 65-68 °C
• Boiling Point: 273.8±23.0 °C(Predicted)
• Appearance: /
• Density: 1.130±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated
• PKA: 3.35±0.10(Predicted)
• CAS DataBase Reference: (E)-4-TERT-BUTOXY-4-OXOBUT-2-ENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-TERT-BUTOXY-4-OXOBUT-2-ENOIC ACID(135355-96-3)
• EPA Substance Registry System: (E)-4-TERT-BUTOXY-4-OXOBUT-2-ENOIC ACID(135355-96-3)

Safety Data

• Hazardous Substances Data: 135355-96-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(E)-4-TERT-BUTOXY-4-OXOBUT-2-ENOIC ACID is used as a reactant for the preparation of cysteine protease inhibitors based on fumaric acid-derived oligopeptides. These inhibitors play a crucial role in the development of new therapeutic strategies for various diseases.
Used in Pulmonary Drug Delivery:
In the pharmaceutical industry, (E)-4-TERT-BUTOXY-4-OXOBUT-2-ENOIC ACID is also used in the preparation of Nε-fumaroylated diketopiperazine of L-Lys, which is utilized for pulmonary drug delivery. This application helps improve the bioavailability and efficacy of drugs targeting the respiratory system.
Chemical Properties:
(E)-4-TERT-BUTOXY-4-OXOBUT-2-ENOIC ACID is a white solid, which contributes to its stability and ease of handling in various chemical processes. Its unique chemical properties make it a valuable compound for the development of new drugs and drug delivery systems.

Upstream product

• 107679-25-4 but-2-enedioic acid tert-butyl ester ethyl ester 
• 298-12-4 Glyoxilic acid 
• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 865-47-4 potassium tert-butylate 
• 108-31-6 maleic anhydride 

Downstream Products

• 936620-75-6 C₂₀H₂₆O₄N₂ 
• 858342-84-4 (4S,5R)-1-(4-bromophenyl)-4,5-dihydro-5-(oxazolidin-2-one-3-carbonyl)-3-phenyl-1H-pyrazole-4-carboxylic acid tert-butyl ester 
• 1189038-30-9 NH₂<-Val<-Ala<-Leu<-C₁(Ac)<-Fum-Gly-Gly-Phe-OH 
• 1189038-29-6 NH₂<-Val<-Leu<-Leu<-C₁(Ac)<-Fum-Gly-Gly-Phe-OH 
• 1189038-28-5 NH₂<-Val<-Leu<-Leu<-Ala<-Fum-Ala-Gly-Phe-OH 
• 1189038-22-9 NH₂<-Val<-Val<-Leu<-Gln<-Fum-Ala-Gly-Phe-OH 
• 1189038-27-4 NH₂<-Val<-Leu<-Leu<-Ala<-Fum-Gly-Gly-Phe-OH 
• 1189038-18-3 NH₂<-Val<-Ala<-Leu<-Asn<-Fum-Gly-Gly-Phe-OH 
• 1189038-21-8 NH₂<-Val<-Leu<-Leu<-Phe<-Fum-Gly-Gly-Phe-OH 
• 1189038-19-4 NH₂<-Val<-Leu<-Phe<-Asn<-Fum-Gly-Gly-Phe-OH 
• 1189038-17-2 NH₂<-Val<-Leu<-Leu<-Asn<-Fum-Gly-Gly-Phe-OH 
• 1213775-78-0 tert-butyl (E)-4-(3-(2,4-dimethoxyphenylcarbamoyl)-1H-indol-1-yl)-4-oxobut-2-enoate 
• 1229354-34-0 (E)-3-((S)-1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-acrylic acid tert-butyl ester 
• 1378314-79-4 tert-butyl (2,6-dimethylphenyl) fumarate 

Relevant articles and documents

Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide

The first synthesis of the tetrasaccharide fragment of the anthracycline natural product Arugomycin is described. A reagent controlled dehydrative glycosylation method involving cyclopropenium activation was utilized to synthesize the α-linkages with complete anomeric selectivity. The synthesis was completed in 20 total steps, and in 2.5% overall yield with a longest linear sequence of 15 steps.

Asymmetric synthesis of β2-homo-tert-leucine via radical addition to enantiopure N-fumaroylhexahydrobenzooxazolidin-2-one

β-Amino acids are key structural elements in unnatural peptides, peptidomimetics, and many other physiologically active compounds. In view of their importance, we have developed an efficient synthetic route that provides highly enantiomerically enriched (

The total synthesis of (±)-fumimycin

The antibiotic agent fumimycin has been synthesized for the first time. This natural product was found to inhibit the bacterial peptide deformylase and may represent a lead structure to a class of novel antibacterials. Our synthetic strategy towards fumimycin involved the following steps: Dakin oxidation of an aldehyde functionality, conversion of an oxime through radical fragmentation to form an N-diphenylphosphoryl group, construction of an α-trisubstituted amine by 1,2-addition to a ketimine, a Claisen rearrangement with subsequent transition-metal-catalyzed olefin isomerization to install a propenyl chain and final amidation. Peptide deformylase (PDF)-inhibitor synthesis: A strategy involving amine formation through addition to a ketimine has been successfully employed for the first total synthesis of the antibiotic agent fumimycin (see scheme).

Syntheses and evaluation of the antioxidant activity of acitretin analogs with amide bond(s) in the polyene spacer

Ester analogs of the antipsoriatic drug acitretin were synthesized by coupling either anilines with N-protected indole-3-carboxylic acid, followed by deprotection and coupling with O-monoprotected dicarboxylic acids or Wittig reaction of indole-3-carboxaldehyde, 3-acetyl-1-tosylpyrrole and 4-amino-9-fluorenone with Ph3P{double bond, long}CHCO2tBu, followed by N-deprotection, where necessary, and finally coupling with cinnamoyl fluorides. Corresponding free acids were obtained through TFA-mediated carboxyl group deprotection. Although these analogs and acitretin showed very low reducing abilities, analogs 5, 6, 8 and 12 strongly inhibited LOX with IC50 values ranging from 35-65 μM. Acitretin and its analogs 5-7, 10, 11 and 15 inhibited lipid peroxidation more strongly than trolox whereas acitretin and analog 4 were in vivo more potent anti-inflammatory agents on rat paw oedema induced by Carrageenan than indomethacin.

On-bead screening of a combinatorial fumaric acid derived peptide library yields antiplasmodial cysteine protease inhibitors with unusual peptide sequences

A new class of cysteine protease inhibitors based on fumaric acid derived oligopeptides was successfully identified from a high-throughput screening of a solid-phase bound combinatorial library. As target enzymes falcipain and rhodesain were used, which play important roles in the life cycles of the parasites which cause malaria (Plasmodium falciparum) and African sleeping sickness (Trypanosoma brucei rhodesiense). The best inhibitors with unusual amino acid sequences not reported before for this type of enzyme were also fully analyzed in detail in solution. Ki values in the lower micromolar and even nanomolar region were found. Some inhibitors are even active against plasmodia and show good selectivity relative to other enzymes. Also the mechanism of action was studied and could be shown to be irreversible inhibition.

Wittig reactions in water media employing stabilized ylides with aldehydes. Synthesis of α,β-unsaturated esters from mixing aldehydes, α-bromoesters, and Ph3P in aqueous NaHCO3

(Chemical Equation Presented) Water is demonstrated to be an effective medium for the Wittig reaction over a wide range of stabilized ylides and aldehydes. Despite sometimes poor solubility of the reactants, good chemical yields normally ranging from 80 to 98% and high E-selectivities (up to 99%) are achieved, and the rate of the reactions in water is unexpectedly accelerated. The efficiency of water as a medium in the Wittig reaction is compared to conventional organic solvents ranging from carbon tetrachloride to methanol. The aqueous Wittig reaction works best when large hydrophobic entities are present, such as aromatic, heterocyclic aromatic carboxaldehydes, and long-chain aliphatic aldehydes with triphenylphosphoranes. The E/Z-isomeric ratio of the Wittig products appears dependent on the electron-accepting/donating capacity and the location of the substituents present in the aromatic ring. The effect of additives, such as benzoic acid, LiCl, and sodium dodecyl sulfate (SDS), on the Wittig reaction has been explored. The Wittig reaction can also be conducted in the presence of acidic entities, such as phenols and carboxylic acids. In addition, large α-substituents in the aliphatic aldehydes do not jeopardize the reaction. It is also demonstrated that hydrates of aldehydes can be used directly in the aqueous Wittig reaction as substrates. The scope of the aqueous Wittig reaction is extended to 24 examples of one-pot mixtures of Ph3P, α-bromoesters, and aldehydes in sodium bicarbonate solution (at 20°C for 40 min to 3 h) to provide Wittig products of up to 99% yield and up to 98% E-selectivity. Since water is inexpensive, extremely easy to handle, and represents no environmental concerns, it should be considered a possible medium for new organic reactions.

Water is an efficient medium for Wittig reactions employing stabilized ylides and aldehydes

Water is demonstrated to be an excellent medium for the Wittig reaction employing stabilized ylides and aldehydes. Although the solubility in water appears to be an unimportant characteristic in achieving good chemical yields and E/Z-ratios, the rate of W

On the Diels-Alder reactions and the Lewis acid induced rearrangements of 6-fumaryl 1,3,8-nonatrienes

6-Fumaryl 1,3,8-nonatrienes substituted at the C5 position by a vinyl group were found to undergo competing tandem sigmatropic rearrangement/Diels-Alder cyclisation when heated under standard Diels-Alder cyclisation conditions. This rearrangement became t

Tandem [4+2]/[3+2] cycloadditions of nitroalkenes. 9. Synthesis of (-)-rosmarinecine

(-)-Rosmarinecine (2) is the necine base portion of the pyrrolizidine alkaloid (-)-rosmarinine. (-)Rosmarinecine is a representative of the group of pyrrolizidines that show a cis relationship between adjacent stereocenters C(1), C(7), and C(7a), in addition to a highly oxygenated skeleton. (-)-Rosmarinecine (2) has been synthesized in eight steps and 14.8% overall yield, as an illustration of a general approach for the construction of pyrrolizidines having this stereochemical feature. The key step in the asymmetric synthesis is a Lewis acid-promoted, tandem inter-[4+2]/intra-[3+2] cycloaddition between a fumaroyloxy nitroalkene and a chiral vinyl ether.

Total synthesis of nosiheptide. Synthesis of thiazole fragments

The preparation of three new thiazole derivatives from natural products is described, as well as improvements in the synthesis of ethyl 2-aminomethyl-4-thiazolecarboxylate.