Trifluoroethyl ester

Figure 6.16 Enantioselective transesterification of N-Cbz-amino acid 2,2,2-trifluoroethyl esters.

Recently, a very interesting preparation of P-peptides has been carried out by Kanerva and coworkers through a two-step lipase-catalyzed reactions in which N-acetylated P-amino esters were first activated as 2,2,2-trifluoroethyl esters with CALB [55]. The activated esters were then used to react with a P-aminoester in the presence of CALA in dry diethylether or diisopropylether (Scheme 7.31). In this peptide synthesis, the aminoester was used in excess and the unreacted counterpart was easily separated and later recyded. 

A combinatorial approach for biocatalytic production of polyesters was demonstrated. A library of polyesters were synthesized in 96 deep-well plates from a combination of divinyl esters and glycols with lipases of different origin. In this screening, lipase CA was confirmed to be the most active biocatalyst for the polyester production. As acyl acceptor, 2,2,2-trifluoroethyl esters and vinyl esters were examined and the former produced the polymer of higher molecular weight. Various monomers such as carbohydrates, nucleic acids, and a natural steroid diol were used as acyl acceptor. 

CioH14F12N204P2, Phosphorohydrazidous acid, 2-[bis(2,2,2-trifluoroethoxy)phosphino]-1,2-dimethyl-, bis(2,2,2-trifluoroethyl) ester, [169175-15-9], 32 134 CioHjjCl oO, Molybdenum, dichlo-... 

Bis(trifluoroethyl) methylphosphonate Phosphonic acid, methyl-, bls(2,2,2-trifluoroethyl) ester (9) (757-95-9)... 

A series of novel 2-amino-6-aryl-9-[2(phosphonomethoxy)ethyl] purine bis (2,2,2-trifluoroethyl) esters (404) has been synthesized by satisfactory regioselec-tive alkylation of 2-amino-6-chloropurine (405) with the bis(tri-fluoroethyl)(2-iodoethoxy)methylphosphonate(406), followed by exchanging the chlorine atom in the resultant intermediate (407) for various substituted and unsubstituted benzenethiols and naphthalenethiols. 6-Phenylthio- and 6-(methoxyphenyl)thio-derivatives showed potent Hepatits B-specific antiviral activity in vitro, and 9[2-(phosphonomethoxy)ethyl] adenine and 9[2-(phosphonomethoxy)ethyl] 2,6-diaminopurine have a broad spectrum of activity against viruses (Scheme 105). ... 

The synthesis of novel HBV-specific antiviral agents, the 2-amino-6-arylthio-9-[2-(phosphonomethoxy)ethyl]purine bis (2,2,2-trifluoroethyl) esters (87a-r) has been reported. These phosphonate diesters were prepared by the reaction of substituted purines with bis-(trifluoroethyl) (2-iodoethoxy)methylphosphonate in the presence of DBU. ... 

PFsNOSiQH, Phosphinimidic acid, P,P-dimethyl-iV-(trimethylsilyl)-2,2,2-trifluoroethyl ester, 25 71 PF6lrCigH22, Phosphate(l-), hexafluoro-, ( n -l,5-cycIooctadiene)bis(pyridine)-iridium(l), 24 174... 

Trifluoroethyl esters can also be used. In one case, Nor O acylation depended on the solvent (9.20).207... 

Kanerva et al. resolved ethyl esters of ten alicyclic (i-aminocarboxylic acids by lipase catalysis in organic solvents. The resolutions were based on acylation of the amino group at the / -stereogenic centre with various 2,2,2-trifluoroethyl esters. From the cis and trans racemic esters 42, all four enantiomers of 2-ACPC were prepared. The absolute configurations of 43 and 44 were proved by transformation to the known 2-ACPC enantiomers by hydrolysis and subsequent desalting with an anion-exchange resin [85]. 

Bis(2,2,2-trifluoroethyl) esters of phosphonoacetic acids have been prepared by the... 

Acyl imidazoUdes. These compounds resemble acyl chlorides in reactivity and are thus useful in synthesis. Masamune has observed that they can be prepared by reaction of phenyl and 2,2,2-trifluoroethyl esters with N-(trimethyl-silyl)imidazole at 20° in the presence of a trace of sodium phenoxide (1). Alkyl... 

Propenoic acid, 2-methyl-, 2,2,2-trifluoroethyl ester. See Trifluoroethyl methacrylate 2-Propenoic acid, 2-methyl-, 3-(trimethoxysilyl) propyl ester. See 3-Methacryloxypropyltrimethoxysilane... 

Propenoic acid, 2,2,2-trifluoroethyl ester. See 2,2,2-Trifluoroethyl acrylate Propenol Propen-1-ol-3 1-Propen-3-ol 2-Propen-1-ol. See Allyl alcohol... 

Synonyms 2-Propenoic acid, 2,2,2-trifluoroethyl ester TFEA... 

W(Trimethylsilyl)imidazole reacts with phenyl and 2,2,2-trifluoroethyl esters under base catalysis to give acylimidazolides (eq 3). These imidazolides show reactivity similar to acyl chlorides and therefore are useful in synthesis. ... 

---