BOC-1,2-TRANS-ACHC-OH - CAS 209128-50-7
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CAS 209128-50-7 BOC-1,2-TRANS-ACHC-OH

Reference Reading

1.Piperidine dispiro-1,2,4-trioxane analogues.
Sabbani S1, Stocks PA, Ellis GL, Davies J, Hedenstrom E, Ward SA, O'Neill PM. Bioorg Med Chem Lett. 2008 Nov 1;18(21):5804-8. doi: 10.1016/j.bmcl.2008.09.052. Epub 2008 Sep 17.
Dispiro N-Boc-protected 1,2,4-trioxane 2 was synthesised via Mo(acac)(2) catalysed perhydrolysis of N-Boc spirooxirane followed by condensation of the resulting beta-hydroperoxy alcohol 10 with 2-adamantanone. N-Boc 1,2,4-trioxane 2 was converted to the amine 1,2,4-trioxane hydrochloride salt 3 which was subsequently used to prepare derivatives (4-7). Several of these novel 1,2,4-trioxanes had nanomolar antimalarial activity versus the 3D7 strain of Plasmodium falciparum. Amine intermediate 3 represents a versatile derivative for the preparation of achiral arrays of trioxane analogues with antimalarial activity.
2.Efficient radiosynthesis of 3'-deoxy-3'-18F-fluorothymidine using electrowetting-on-dielectric digital microfluidic chip.
Javed MR1, Chen S, Kim HK, Wei L, Czernin J, Kim CJ, van Dam RM, Keng PY. J Nucl Med. 2014 Feb;55(2):321-8. doi: 10.2967/jnumed.113.121053. Epub 2013 Dec 23.
Access to diverse PET tracers for preclinical and clinical research remains a major obstacle to research in cancer and other disease research. The prohibitive cost and limited availability of tracers could be alleviated by microfluidic radiosynthesis technologies combined with a high-yield microscale radiosynthetic method. In this report, we demonstrate the multistep synthesis of 3'-deoxy-3'-(18)F-fluorothymidine ((18)F-FLT) with high yield on an electrowetting-on-dielectric (EWOD) microfluidic radiosynthesizer, previously developed in our group. We have identified and established several parameters that are most critical in the microscale radiosynthesis, such as the reaction time, reagent concentration, and molar ratios, to successfully synthesize (18)F-FLT in this compact platform.
3.Phagocytic uptake and ROS-mediated cytotoxicity in human hepatic cell line of amphiphilic polyphosphazene nanoparticles.
Qiu L1, Chen Y, Gao M, Zheng C, Zhao Q. J Biomed Mater Res A. 2013 Jan;101(1):285-97. doi: 10.1002/jbm.a.34323. Epub 2012 Sep 11.
The pH-responsive amphiphilic polyphosphazenes bearing N,N-diisopropylethylenediamine (DPA) have been proven to be promising nanovehicles for drug antitumor therapy. To further modify these amphiphilic polyphosphazenes with fluorescent labeling agent or other biochemical functional groups, serine methyl ester containing active chemical group NH(2) was chosen to be introduced to get a novel polymer [NP(PEG)(0.24) (DPA)(0.5)(SME)(1.26) (n) (PDS-NH(2) ). Considering the possible toxic effect of -NH(2) group, the biocompatibility in bloodstream and nanotoxicity on human normal hepatic L-02 cells was evaluated in this study. The polymer [NP(PEG)(0.24)(DPA)(0.5)(SME-BOC)(1.26)](n) (PDS-BOC) linked with tert-butyloxycarbonyl groups to protect and hide -NH(2) group was applied as the comparison. First, the bovine serum albumin (BSA) adsorption and phagocytic uptake behavior in human THP-1 macrophages were performed. The results suggested that only a minor percentage of the nanoparticles were involved in BSA binding and phagocytic uptake as the result of PEGylation on the particulate surface.
4.Synthesis of 1-substituted tetrahydroisoquinolines by lithiation and electrophilic quenching guided by in situ IR and NMR spectroscopy and application to the synthesis of salsolidine, carnegine and laudanosine.
Li X1, Leonori D, Sheikh NS, Coldham I. Chemistry. 2013 Jun 10;19(24):7724-30. doi: 10.1002/chem.201301096. Epub 2013 May 15.
The lithiation of N-tert-butoxycarbonyl (N-Boc)-1,2,3,4-tetrahydroisoquinoline was optimized by in situ IR (ReactIR) spectroscopy. Optimum conditions were found by using n-butyllithium in THF at -50 °C for less than 5 min. The intermediate organolithium was quenched with electrophiles to give 1-substituted 1,2,3,4-tetrahydroisoquinolines. Monitoring the lithiation by IR or NMR spectroscopy showed that one rotamer reacts quickly and the barrier to rotation of the Boc group was determined by variable-temperature NMR spectroscopy and found to be about 60.8 kJ mol(-1), equating to a half-life for rotation of approximately 30 s at -50 °C. The use of (-)-sparteine as a ligand led to low levels of enantioselectivity after electrophilic quenching and the "poor man's Hoffmann test" indicated that the organolithium was configurationally unstable. The chemistry was applied to N-Boc-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline and led to the efficient synthesis of the racemic alkaloids salsolidine, carnegine, norlaudanosine and laudanosine.