93836-48-7

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 56777-24-3 benzyl (S)-Lactate 
• 100-39-0 benzyl bromide 
• 2051-96-9 benzyl lactate 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 139929-03-6 benzyl (R)-N,N-bis(t-butoxycarbonyl)<15N>alaninate 
• 82717-96-2 [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine 
• 85196-26-5 (2R)-2-amino>propionic acid 
• 82717-95-1 Benzyl (2S)-2-amino>propionate 
• 93841-86-2 benzyl (2R)-2-amino>propionate 
• 193814-86-7 (R)-2-[(S)-3-(Biphenyl-4-yloxy)-1-((S)-6-methylcarbamoyl-tetrahydro-pyridazine-1-carbonyl)-propylamino]-propionic acid benzyl ester 
• 174563-09-8 benzyl (2R)-2-<4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl>propanoate 
• 174563-12-3 benzyl (2R)-2-<3-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-2,3-dihydro-2-oxo-1H-imidazol-1-yl>propanoate 
• 309761-66-8 (1S,2S,4R,5S)-4-((S)-1-Benzyloxycarbonyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 
• 301184-67-8 (R)-2-[(3R,4S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-phenyl-pyrrolidin-1-yl]-propionic acid benzyl ester 
• 758723-41-0 (1S,2S,4R,5S)-4-((R)-1-Benzyloxycarbonyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid 2-tert-butyl ester 1-methyl ester 
• 309761-65-7 (1S,2S,4R,5S)-4-((R)-1-Benzyloxycarbonyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 
• 494870-68-7 (R)-N-allyloxyalanine benzyl ether 
• 1192364-59-2 C₂₂H₃₈N₄O₂ 

Relevant academic research and scientific papers

ANTHELMINTIC DEPSIPEPTIDE COMPOUNDS

The present invention provides cyclic depsipeptide compounds of formula (I) wherein the stereochemical configuration of at least one carbon atom bearing the groups Cy1, Cy2, R1, R2, R3, R4, Ra and Rb is inverted compared with the naturally occurring cyclic depsipeptide PF1022A. The invention also provides compositions comprising the compounds that are effective against parasites that harm animals. The compounds and compositions may be used for combating parasites in or on mammals and birds. The invention also provides for an improved method for eradicating, controlling and preventing parasite infestation in birds and mammals.

ANTHELMINTIC DEPSIPEPTIDE COMPOUNDS

The present invention provides cyclic depsipeptide compounds of formula (I) and compositions comprising the compounds that are effective against parasites that harm animals. The compounds and compositions may be used for combating parasites in or on mammals and birds. The invention also provides for an improved method for eradicating, controlling and preventing parasite infestation in birds and mammals.

NEW GADOLINIUM CHELATE COMPOUNDS FOR USE IN MAGNETIC RESONANCE IMAGING

The present invention relates to a new class of high relaxivity extracellular gadolinium chelate complexes, to methods of preparing said compounds, and to the use of said compounds as MRI contrast agents.

DOTA-M8: An extremely rigid, high-affinity lanthanide chelating tag for PCS NMR spectroscopy

A new lanthanide chelating tag (M8) for paramagnetic labeling of biomolecules is presented, which is based on an eight-fold, stereoselectively methyl-substituted DOTA that can be covalently linked to the host molecule by a single disulfide bond. The steric overcrowding of the DOTA scaffold leads to an extremely rigid, kinetically and chemically inert lanthanide chelator. Its steric bulk restricts the motion of the tag relative to the host molecule. These properties result in very large pseudocontact shifts (>5 ppm) and residual dipolar couplings (>20 Hz) for Dy-M8 linked to ubiquitin, which are unprecedented for a small, single-point-attachment tag. Such large pseudocontact shifts should be well detectable even for larger proteins and distances beyond ～50 A. Due to its exceptionally high stability and lanthanide affinity M8 can be used under extreme chemical or physical conditions, such as those applied for protein denaturation, or when it is undesirable that buffer or protein react with excess lanthanide ions.

Stereoselective synthesis of multiply substituted [1,2]oxazinan-3-ones via ring-closing metathesis

The title compounds are α-amino acids whose nitrogen atoms are enclosed within 4,5-disubstituted, six-membered cyclic hydroxamates and they are of interest as potential β-lactam surrogates. The compounds have been synthesized in the present work by functionalization of the double bonds of N-substituted 6H-[1,2]oxazin-3-ones, which are obtained upon successive reaction of the inflates of 5-α-hydroxy esters with O-allylhydroxylamine and acryloyl chloride, followed by cyclization of the resulting A-α-TV- acryloyl-N-allyloxyamino esters in the presence of the ring-closing metathesis (RCM) catalyst bis(tricyclohexylphosphine)benzylideneruthenium dichloride. The olefins are also accessible, but less efficiently so, by a Wittig sequence that employs bromoacetyl bromide in place of acryloyl chloride, followed successively by triphenylphosphine, silver triflate, ozonolysis, and cyclization. Asymmetric dihydroxylation of these chiral olefins affords a single diastereomer in high yield having either the αR,4S,5S- or the αR,4R,5R configuration, depending on the auxiliary. The configuration of the αR,4R,5R isomer has been confirmed by its conversion to (αR,4S,5R)-2-(α-carboxyethyl)-4- phenylacetylamino-5-hydroxy-1,2-oxazinan-3-one, whose αR,4K,5S diastereomer was previously prepared from L-ascorbic acid. With N-bromosuccinimide in aqueous dimethylformamide, a 6H-[1,2]oxazin-3-one afforded a separable 1:1 mixture of bromohydrins, which could be cyclized to epoxides or hydrogenolyzed to 5-hydroxy-1,2-oxazinan-3-ones.

Synthesis and cholera toxin binding properties of multivalent GM1 mimics

Dendrimers based on the 3,5-di-(2-aminoethoxy)-benzoic acid branching unit were used to attach multiple copies of a GM1 mimic for inhibition of cholera toxin binding. Systems up to octavalent were synthesized along with relevant reference compounds that contained in one case the ligand in a monovalent format and in another case the scaffold but not the ligand. Using a surface plasmon resonance inhibition assay the prepared inhibitors showed good inhibition. While the monovalent GM1 mimic showed the expected inhibition in the 200 μM range the multivalent scaffolds led to increased binding. The tetravalent compound was shown to be 440-fold more potent than its monovalent counterpart. The octavalent analog, however, was the most potent compound as determined using an ELISA assay.

Optically active antifungal azoles. IX. An alternative synthetic route for 2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol- 1-yl)propyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)1,2,4- triazolone and its analogs

A new route for the synthesis of the optically active antifungal azole TAK-187, 2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4- triazol-1-yl)propyl]-4-[4-(2,2,3,3-tetrafluoroptopoxy)phenyl]3(2H,4H)-1,2,4- triazolone, was established. The key synthetic intermediate, 2-[(1R)-2-(2,4- difluorophenyl)-2-oxo-1-methylethyl]-4-[4-(2,2,3,3- tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (8), was prepared starting from the esters (11a, b) of (S)-lactic acid in a stereocontrolled manner. This optically active propiophenone derivative 8 was converted to the one carbon-elongated (1R,2S)-diol 7, which was then reacted with 1H-1,2,4- triazole to yield TAK-187. This newly developed route was applied to the synthesis of the analogs (25a, b - 28a, b) containing an imidazolone or imidazolidinone nucleus.

Production of optically active triazole compounds and their intermediates

A compound of the formula (V): STR1 wherein Ar' is a halogenated phenyl group, R is a hydrocarbon residue having a functional group at the α-carbon, R3' is an optionally substituted aliphatic or aromatic hydrocarbon residue or an optionally substituted aromatic heterocyclic group, Y and Z are, the same or different, a nitrogen atom or a methine group optionally substituted with a lower alkyl group, and (R) and (S) represent configurations, which is an optically active intermediate for production of optically active triazole compounds (I): STR2 wherein the symbols have the same meanings as defined above, and methods of preparing the compounds (V) and (I).

Asymmetric Synthesis of 2,3-Disubstituted Succinates via Chiral Oxazolidinone Controlled Displacement of α-Trifluoromethanesulfonate Substituted Esters

The addition of chiral imides to α-trifluoromethanesulfonate esters gave chiral 2,3-disubstituted succinates with moderate to excellent diastereoselectivity and in good overall chemical yields.Both syn and anti chiral products are attainable via this methodology, with generally better diastereoselectivity and chemical yields observed in the production of the syn products.The reactions proceed through the predicted SN2 displacement of the triflate leaving group, as inferred from the absolute configuration of the products.