60176-77-4Relevant academic research and scientific papers
IMMOBILIZED PORCINE LIVER ESTERASE: A CONVENIENT REAGENT FOR THE PREPARATION OF CHIRAL BUILDING BLOCKS
Laumen, Kurt,Reimerdes, Ernst H.,Schneider, Manfred,Goerisch, Helmut
, p. 407 - 410 (1985)
A simple method for the effective, covalent, immobilization of porcine liver esterase (PLE) is described, and the application of this reagent for the preparation of chiral building blocks on a 50-500 mmol scale is demonstrated.
Selective synthesis of ent-15-epi-F2t-isoprostane and a deuterated derivative
Shizuka, Manami,Snapper, Marc L.
, p. 2397 - 2403 (2007)
Isoprostanes are an emerging class of lipid metabolites whose physiological properties are not well understood. The selective synthesis of ent-15-epi-F2t-isoprostane, an isomer active in a preliminary screening assay is described. The synthesis features a regioselective cross-metathesis on an enantiomerically enriched divinyl cyclopentyl intermediate to selectively differentiate the side-chains of the target. The route provides the isoprostane, as well as a d4-labeled analogue, in 14 steps from readily available starting materials. Georg Thieme Verlag Stuttgart.
Resolution of cis-4-O-TBS-2-cyclopenten-1,4-diol
Curran, Timothy T.,Hay, David A.
, p. 2791 - 2792 (1996)
The resolution of cis-4-O-TBS-2-cyclopenten-1,4-diol with a few different enzymes in organic medium is described. The optical purity and yield of both the alcohol and acetate were moderate to excellent.
A practical and scalable process for 4-(R)-hydroxycyclopent-2-en-1-(S)- acetate by desymmetrization of meso-cyclopent-2-en-1,4-diacetate catalyzed by Trichosporon beigelii (NCIM 3326), a cheap biocatalyst
Kalkote, Uttam R.,Ghorpade, Sandeep R.,Joshi, Rohini R.,Ravindranathan,Bastawade, Kulbhushan B.,Gokhale, Digambar V.
, p. 2965 - 2970 (2000)
Various yeast and fungal cultures from NCIM, NCL, Pune, India were screened for the hydrolysis of meso-cyclopent-2-en-1,4-diacetate 2 to 4-(R)- hydroxycyclopen-2-en-1-(S)-acetate 1 to provide a cheaper and more effective alternative to PLE which is currently being used for the conversion. Yeast cultures of Trichosporon species were identified as having a pro-R preference in the hydrolysis of 2; but the enantioselectivity was poor. Hence detailed medium-engineering investigations were made for the hydrolysis of 2 to 1 using a culture of Trichosporon beigelii (NCIM 3326) as catalyst. Addition of 10% v/v ethanol was found to enhance the enantioselectivity of the enzyme, affording 1 of 85% optical purity (op) in 83% yield. Further exploration of inherent consecutive kinetic resolutions to the desymmetrization afforded 1 of > 98% op in 74% chemical yield. (C) 2000 Elsevier Science Ltd.
Recombinant Pig Liver Esterase-Catalyzed Synthesis of (1S,4R)-4-Hydroxy-2-cyclopentenyl Acetate Combined with Subsequent Enantioselective Crystallization
Hinze, Janine,Süss, Philipp,Strohmaier, Silja,Bornscheuer, Uwe T.,Wardenga, Rainer,Von Langermann, Jan
, p. 1258 - 1264 (2016)
The recombinant pig liver esterase catalyzed hydrolysis of cis-1,4-diacetoxy-2-cyclopentene forming (1S,4R)-4-hydroxy-2-cyclopentenyl acetate was investigated and realized at preparative scale. Relevant reaction conditions were examined and optimized to achieve full conversion with an enantiomeric excess of about 86% ee. Enantiopure product was then obtained after enantioselective crystallization, which required further studies of the solid phase behavior, including its binary melting point phase diagram.
Synthesis of tetranor-PGE1: A urinary metabolite of prostaglandins E1 and E2
Kimbrough, Jennifer R.,Jana, Somnath,Kim, Kwangho,Allweil, Alexander,Oates, John A.,Milne, Ginger L.,Sulikowski, Gary A.
supporting information, (2020/04/21)
Prostaglandin E2 is produced in response to inflammation, often associated with human disease. As prostaglandins are rapidly metabolized, quantification of end urinary metabolites depend on chemical synthesis of isotopically labeled standards to support metabolite quantification. A concise synthesis of tetranor-PGE1 is described including a late stage incorporation of an isotopically labeled side-chain.
Stereoselective Synthesis for Potential Isomers of Ticagrelor Key Starting Material
Mahender, Madaraboina,Yakambaram,Pandey, Jaya,Chandrashekar,Reddy, L. Amarnath,Jayashree,Bandichhor, Rakeshwar
, p. 2866 - 2872 (2019/08/30)
Tartrate salt of carbocyclic amine 2 is one of the key starting materials for the synthesis of Ticagrelor 1. During the synthesis of 1, the isomers of 2 also need to be considered as potential impurities and characterized before establishing the specification of product. In the present work, detailed study has been carried out to synthesize the related substances of 2, and their structure characterization has been discussed.
Preparation of (1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate via Novozym-435 catalyzed desymmetrization of cis-3,5-Diacetoxy-1-cyclopentene
Putta, Shekhar,Reddy, Annem Mallikarjun,Sheelu, Gurrala,Reddy, B.V. Subba,Kumaraguru, Thenkrishnan
, p. 6673 - 6679 (2018/10/15)
Photooxidation of cyclopentadiene has been carried out in methanol using white light of LED lamp, rose bengal as photo initiator, and compressed air at 0 °C. Under conditions of [thiourea] ? [cyclopentadiene], the consumption of thiourea follows a pseudo-first-order reaction kinetics with half life of 75 ± 10 min; corr. coeff. r = 0.989. Slow addition of the monomer and maintaining excess thiourea concentration in reaction mass improves the yield. cis-3,5-Dihydroxy-1-cyclopentene is acetylated without isolation to obtain cis-3,5-Diacetoxy-1-cyclopentene of high purity (>99%) with overall isolated yield of 30%. Desymmetrization of the diacetate to (1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate has been carried out via enzymatic transesterification with methanol in methyl tert-butyl ether (MTBE) at 5 °C using Novozym-435. The enantiomerically pure monoacetate (e.e. >99%) was obtained in 95% isolated yield. The recovered enzyme was reused for more than 10 times without loss in yield and selectivity. The entire protocol does not require purification of final product by chromatography.
Cobalt versus Osmium: Control of Both trans and cis Selectivity in Construction of the EFG Rings of Pectenotoxin 4
Roushanbakhti, Ahria,Liu, Yifan,Winship, Paul C. M.,Tucker, Michael J.,Akhtar, Wasim M.,Walter, Daryl S.,Wrigley, Gail,Donohoe, Timothy J.
supporting information, p. 14883 - 14887 (2017/10/24)
Catalytic oxidative cyclisation reactions have been employed for the synthesis of the E and F rings of the complex natural product target pectenotoxin 4. The choice of metal catalyst (cobalt- or osmium-based) allowed for the formation of THF rings with either trans or cis stereoselectivity. Fragment union using a modified Julia reaction then enabled the synthesis of an advanced synthetic intermediate containing the EF and G rings of the target.
Novel Imidazo[4,5-c]Quinoline And Imidazo[4,5-c][1,5]Naphthyridine Derivatives As LRRK2 Inhibitors
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Paragraph 0171, (2017/04/04)
The present invention provides novel imidazo[4,5-c]quinoline and imidazo[4,5-c][1,5]naphthyridine derivatives of Formula (I), and the pharmaceutically acceptable salts thereof wherein R1, R1a, R1b, R2, R4, R5, R6, X and Z are as defined in the specification. The invention is also directed to pharmaceutical compositions comprising the compounds of Formula (I) and to use of the compounds in the treatment of diseases associated with LRRK2, such as neurodegenerative diseases including Parkinson's disease or Alzheimer's disease, cancer, Crohn's disease or leprosy.
