Chiralpak ad h column

Manufactured by Daicel

Sourced in Japan

The Chiralpak AD-H column is a high-performance liquid chromatography (HPLC) column designed for the separation and analysis of chiral compounds. It utilizes a stationary phase consisting of amylose derivatized with 3,5-dimethylphenylcarbamate, which provides effective enantioseparation of a wide range of chiral analytes.

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Lab products found in correlation

Dpx 500, by Bruker (1 mentions) Dpx 400 spectrometer, by Bruker (1 mentions) Q exactive, by Thermo Fisher Scientific (1 mentions) Lc 2030 plus, by Shimadzu (1 mentions) Tsq quantum ultra am mass spectrometer, by Thermo Fisher Scientific (1 mentions) Ipds 2t, by STOE (1 mentions) Lh 20, by GE Healthcare (1 mentions) Lc 6ad instrument, by Shimadzu (1 mentions) 7890a instrument, by Agilent Technologies (1 mentions) 1100 series lc msd ion trap mass spectrometer, by Agilent Technologies (1 mentions) Ods a column, by Shimadzu (1 mentions) Aviii hd 600, by Bruker (1 mentions) V 650 spectrophotometer, by Jasco (1 mentions)

Close spelling variants of this product

Chiralpak AD-H Chiralpak AD

50 protocols using chiralpak ad h column

Stereoselective Synthesis of Benzhydryl Alcohol

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¹H-NMR (CDCl₃, 400 MHz) δ 7.37 (d, J = 7.2 Hz, 2H), 7.27–7.07 (m, 8H), 6.99–6.93 (m, 4H), 6.48 (d, J = 8.0 Hz, 2H), 6.90–6.86 (m, 1H), 5.25 (d, J = 10.0 Hz, 1H), 4.86 (d, J = 10.4 Hz, 1H), 4.04 (brs, 1H), 2.64 (s, 3H). ¹³C-NMR (CDCl₃, 100 MHz) δ 151.20, 140.59, 134.60, 129.03, 128.66, 128.11, 127.86, 127.66, 127.55, 127.50, 120.15, 117.53, 73.51, 71.40, 32.56. Enantiomeric excess was determined by HPLC with a Chiralpak AD-H column (Daicel) (n-hexane/2-PrOH = 95/5, 1.0 mL min⁻¹, 254 nm).

Tanaka K., Kinoshita M., Kayahara J., Uebayashi Y., Nakaji K., Morawiak M, & Urbanczyk-Lipkowska Z. (2018). Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts. RSC Advances, 8(49), 28139-28146.

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Enantioselective Synthesis of 2-Methyl-4'-Methoxyphenyl Compound

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¹H-NMR (CDCl₃, 400 MHz) δ 7.06 (d, 2H, J = 8.4 Hz), 6.86 (d, 2H, J = 8.8 Hz), 3.66–3.59 (m, 1H), 3.33–3.27 (m, 1H), 2.71 (s, 3H), 2.26 (s, 3H), 2.21–2.16 (m, 1H), 1.77–1.63 (m, 3H). ¹³C-NMR (CDCl₃, 100 MHz) δ 149.20, 129.50, 128.11, 116.22, 69.82, 67.66, 33.23, 31.26, 25.45, 25.43, 24.26, 20.26. Enantiomeric excess was determined by HPLC with a Chiralpak AD-H column (Daicel) (n-hexane/2-PrOH = 95/5, 1.0 mL min⁻¹, 254 nm).

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Asymmetric Reduction of Benzophenone

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¹H-NMR (CDCl₃, 400 MHz) δ 7.20–7.09 (m, 10H), 7.04–7.00 (t, J = 8.0 Hz, 2H), 6.62 (t, J = 7.6 Hz, 1H), 6.48 (d, J = 8.0 Hz, 2H), 4.68 (d, J = 6.0 Hz, 1H), 4.42 (d, J = 6.0 Hz, 1H), 2.87 (brs, 1H). ¹³C-NMR (CDCl₃, 100 MHz) δ 147.25, 140.54, 140.22, 129.05, 128.57, 128.26, 127.89, 127.52, 127.26, 126.54, 117.89, 114.11, 78.05, 64.70. Enantiomeric excess was determined by HPLC with a Chiralpak AD-H column (Daicel) (n-hexane/2-PrOH = 95/5, 1.0 mL min⁻¹, 254 nm).

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Asymmetric Synthesis of Benzhydrol Derivatives

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¹H-NMR (CDCl₃, 400 MHz) δ 8.01–7.95 (m, 1H), 7.78–7.70 (m, 1H), 7.52–7.42 (m, 2H), 7.39–7.26 (m, 8H), 7.26–7.07 (m, 3H), 6.29 (d, J = 7.3 Hz 1H), 5.55 (s, 1H), 5.05 (d, J = 5.5 Hz, 1H), 4.72 (d, J = 5.5 Hz, 1H), 2.44 (s, 1H). ¹³C-NMR (CDCl₃, 100 MHz) δ 142.11, 140.65, 139.94, 134.19, 128.64, 128.59, 128.34, 127.99, 127.58, 127.19, 126.49, 126.35, 125.64, 124.80, 123.92, 120.00, 117.64, 106.54, 78.28, 64.36. Enantiomeric excess was determined by HPLC with a Chiralpak AD-H column (Daicel) (n-hexane/2-PrOH = 95/5, 1.0 mL min⁻¹, 254 nm).

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Purification and Characterization of Stereoisomeric SLs

Cited 1 time

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The synthetic rac-GR5 was purchased from Fuji Molecular Planning (Yokohama, Japan), and (+)-GR5 and (−)-GR5 were separated by chiral HPLC with a CHIRALPAK AD-H column (1.0 cm × 25 cm × 5 µm) (DAICEL, Osaka, Japan). The isocratic elution was carried out with n-hexane/2-propanol/methyl tert-butyl ether (80:10:10) at a flow rate of 4.8 ml/min. The synthetic rac-GR24 was purchased from Chiralix (Nijmegen, Netherlands). KAR₁ was purchased from Toronto Research Chemicals (Toronto, Canada). The other synthetic SL derivatives, stable isotope-labeled SLs, natural SLs (solanacol and zealactone) and enzymatically produced BSB using MpaMAX1 are described earlier (Xie et al. 2007 (link), Akiyama et al. 2010 (link), Abe et al. 2014 (link), Seto et al. 2014 (link), Xie et al. 2017 (link), Kodama et al. 2022 ).

Mashiguchi K., Morita R., Tanaka K., Kodama K., Kameoka H., Kyozuka J., Seto Y, & Yamaguchi S. (2023). Activation of Strigolactone Biosynthesis by the DWARF14-LIKE/KARRIKIN-INSENSITIVE2 Pathway in Mycorrhizal Angiosperms, but Not in Arabidopsis, a Non-mycorrhizal Plant. Plant and Cell Physiology, 64(9), 1066-1078.

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Novel Synthetic Approach for Chiral Compounds

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All solvents and chemical reagents were purchased from Aladdin Reagent (Shanghai, China) and Energy Chemical (Shanghai, China), respectively. The melting points of all novel compounds were determined on an X-4B microscope melting point apparatus and were uncorrected (Shanghai Electrophysics Optical Instrument Co., LTD, Shanghai, China). Reactions were detected by thin-layer chromatography (TLC) and visualized under UV light at 254 nm. All ¹H NMR and ¹³C NMR spectra data were recorded on a Bruker DPX-500 or a DPX-400 spectrometer (Bruker, Billerica, MA, USA), DMSO-d₆ or CDCl₃ were used as solvents, and tetramethylsilane was used as an internal standard. The high-resolution mass spectrometer (HRMS) data of the compounds were obtained using a Thermo Scientific Q-Exactive (Thermo Scientific, Missouri, MO, USA). The purity of that compounds was detected by HPLC, which was performed on a Shimadzu LC-2030 Plus (Shimadzu, Tokyo, Japan) with a Daicel Chiralpak AD-H column (conditions: 10% Isopropyl alcohol/Hexanes, 1.0 mL/min, λ = 220 nm, 30 °C). Chromatography was conducted on silica gel 200–300 mesh (Fluka, Daicel (China) investment Co., LTD, Shanghai, China) and under low pressure. The general experimental procedures that were used for the synthesis of all of the compounds is described in the following paragraphs.

Liu D., Luo L., Wang Z., Ma X, & Gan X. (2022). Design, Synthesis and Antifungal/Nematicidal Activity of Novel 1,2,4-Oxadiazole Derivatives Containing Amide Fragments. International Journal of Molecular Sciences, 23(3), 1596.

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Asymmetric Synthesis of Chiral Benzofuranone

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42.0 mg, 84% yield, white solid, mp 135–136 °C; purified by chromatography on silica gel, eluting with ethyl acetate/petroleum ether 1 : 20 (v/v); R_f = 0.3. ¹H NMR (500 MHz, CDCl₃) δ 7.98 (d, J = 8.0 Hz, 1H), 7.83 (m, 2H), 7.78–7.73 (m, 2H), 7.73–7.68 (m, 1H), 7.53 (m, 1H), 7.29 (t, J = 7.5 Hz, 1H), 1.81 (s, 3H); ¹³C NMR (125 MHz, CDCl₃) δ 197.4, 169.6, 151.7, 145.6, 137.4, 134.4, 131.1, 129.5, 127.5, 125.3, 125.24, 125.16, 122.8, 118.6, 73.6, 25.9. HRMS m/z (ESI+): calculated for C₁₆H₁₁NO₂Na ([M + Na]⁺): 272.0682, found 272.0672. For the reaction with (R,R,R)-phosphoramide-PE as a chiral ligand: 30% yield, 63% ee [Daicel Chiralpak AD-H column (25 cm × 0.46 cm ID), ⁿhexane/ⁱPrOH = 95/5, 0.7 mL min⁻¹, 254 nm; t_major = 18.6 min, t_minor = 21.4 min].

Liang R.X., Wang K., Song L.J., Sheng W.J, & Jia Y.X. (2019). Synthesis of tetracyclic indolin-3-ones through Pd-catalyzed intramolecular deacetylative dearomatization of 3-acetoxy-indoles. RSC Advances, 9(25), 13959-13967.

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Chiral Separation of 2-HG Enantiomers

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Bis-PFB ester derivatives of the 2-HG enantiomers were separated using a Chiralpak AD-H column (250 × 4.6 mm i.d., 5 μm; Daicel Chemical Industries, Ltd., Tokyo, Japan) at a flow rate of 1 mL/min. Solvent A was hexanes, and solvent B was IPA/MeOH (1:1; v/v). The linear gradient was as follows: 1% B for 3 min, increased to 60% B over 32 min, and held for 4 min, down to 1% B over 1 min prior to a 5 min equilibration. The separation was performed at 30 °C, and a postcolumn addition (0.75 mL/min MeOH) was used. MS analysis was conducted on a Thermo Scientific TSQ Quantum Ultra AM mass spectrometer (Thermo Scientific, San Jose, CA, USA) equipped with an APCI source operating in negative mode. The TSQ Quantum operating conditions were as follows: vaporizer temperature, 350 °C; heated capillary temperature, 300 °C; and corona discharge needle, 30 μA. The sheath gas (nitrogen) and auxiliary gas (nitrogen) pressures were 35 and 10 (arbitrary units), respectively. Collision-induced dissociation used argon as the collision gas at 1.5 mTorr.

Worth A.J., Gillespie K.P., Mesaros C., Guo L., Basu S.S., Snyder N.W, & Blair I.A. (2015). Rotenone Stereospecifically Increases (S)-2-Hydroxyglutarate in SH-SY5Y Neuronal Cells. Chemical research in toxicology, 28(5), 948-954.

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Stereoselective Synthesis of (3R,4S)-3-Naphthylacetate

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The reaction was performed following Method A, quenching with HCl (0.1 M), using sulfoxonium salt (±)-2a, (S)-Koga amine 5, and 1-naphthylacetic acid 1d. (+)-3g was isolated as a white solid (32.3 mg, 45%, mp 133–135 °C) with a dr = 7:1 as determined by GC-MS analysis of the crude. 15.2 mg of the major isomer was crystallized from isopropanol to >99% optical purity as shown by chiral HPLC analysis. X-ray crystal analysis determined the stereochemistry of the major isomer to be (3R,4S) (see cif-3g in supporting information); HPLC analysis: 50% ee [Daicel Chiralpak AD-H column; 1 mL/min; solvent system: 10% isopropanol in hexane; retention time: 15.1 min (minor), 23.6 min (major)];

{[α]}_{D}^{24}

= +69.7 (c = 0.67, CH₂Cl₂); IR (thin film): 1770, 1146, 703 cm⁻¹; ¹H (400 MHz, CDCl₃, TMS) for the major diastereomer: δ 7.86 (d, J = 8.4 Hz, 1H), 7.80–7.77 (m, 1H), 7.64 (d, J = 8.2 Hz, 1H), 7.50–7.42 (m, 2H), 7.20–7.16 (m, 1H), 6.99–6.89 (m, 4H), 6.67–6.65 (m, 2H), 5.02 (d, J = 8.6 Hz, 1H), 4.88–4.76 (m, 2H), 4.27–4.22 (m, 1H); ¹³C NMR (100 MHz, CDCl₃) for the major diastereomer: δ 176.8, 137.4, 133.7, 132.2, 129.3, 129.2, 128.4, 128.2, 127.6, 127.5, 126.5, 125.7, 125.3, 122.5, 71.8, 48.3, 47.2; MS (EI 70eV): 288, 243, 168, 153, 77 m/z; (M + H)⁺ HRMS m/z calcd for C₂₀H₁₇O₂⁺: 289.1229; found: 289.1221.

Peraino N.J., Kaster S.H., Wheeler K.A, & Kerrigan N.J. (2016). Asymmetric synthesis of γ-lactones through Koga amine-controlled addition of enediolates to α,β-unsaturated sulfoxonium salts. The Journal of organic chemistry, 82(1), 606-615.

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Enantioselective Fluorinated Organic Synthesis

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The reaction was carried out following the general procedure. ¹H-NMR of the crude showed a 60% yield for catalyst V and 55% for catalyst I. The crude mixture was purified by flash column chromatography (hexane : EtOAc = 9 : 1) and the title compound was obtained as a yellowish oil in 93% (catalyst V) and 92% (catalyst I) enantiomeric excess. The ee was determined by HPLC analysis on a Daicel Chiralpak AD-H column: hexane/i-PrOH 95 : 5, flow rate 1.0 mL min⁻¹, λ = 254 nm: τ_V = 10.6 min, τ_I = 8.8 min. [α]²⁵_D + 292.0 (c 1.0, CHCl₃). HRMS-ESI-ORBITRAP (+): calculated for [C₂₇H₂₇BrF₃NNaO₅]⁺ 604.0922, found 604.0928 [M + Na]⁺.¹H-NMR (300 MHz, CDCl₃) δ 7.76 (d, J = 8.9 Hz, 1H), 7.34–7.27 (m, 4H), 7.06 (d, J = 2.6 Hz, 1H), 6.92–6.79 (m, 2H), 6.24 (d, J = 15.7 Hz, 1H), 5.45 (s, 1H), 4.31 (d, J = 12.6 Hz, 1H), 3.79 (s, 3H), 2.83 (d, J = 12.6 Hz, 1H), 2.31 (s, 3H), 1.65 (s, 9H). ¹⁹F-NMR (282 MHz, CDCl₃) δ −81.30. ¹³C-NMR (75 MHz, CDCl₃) δ 168.8, 156.4, 152.6, 148.8, 134.4, 133.9, 131.9, 131.9, 130.3, 129.6, 128.9, 128.0, 127.1, 124.4, 124.3, 115.4, 112.8, 111.5, 84.8, 77.8 (m, tetrasubstituted aliphatic carbon, partially overlapped with CDCl₃), 55.7, 42.0, 28.1, 27.8.

Crotti S., Belletti G., Di Iorio N., Marotta E., Mazzanti A., Righi P, & Bencivenni G. (2018). Asymmetric vinylogous aldol addition of alkylidene oxindoles on trifluoromethyl-α,β-unsaturated ketones. RSC Advances, 8(58), 33451-33458.

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