All reactions in organic medium were performed in standard oven-dried glassware under an inert atmosphere of nitrogen using freshly distilled solvents. CH2Cl2 was distilled from CaH2 and DMF from ninhydrin, and kept over molecular sieves. Solvents and reagents were deoxygenated when necessary by purging with nitrogen. Water used for lyophilization of final dendrimers was nanopure grade, purified through Barnstead NANOPure II Filter with Barnstead MegOhm-CM Sybron meter. All reagents were used as supplied without prior purification unless otherwise stated, and obtained from Sigma-Aldrich Chemical Co. Ltd. Reactions were monitored by analytical thin-layer chromatography using silica gel 60 F254 precoated plates (E. Merck) and compounds were visualized by 254 nm light, a mixture of iodine/silica gel and/or mixture of ceric ammonium molybdate solution (100 mL H2SO4, 900 mL H2O, 25 g (NH4)6Mo7O24H2O, 10 g Ce(SO4)2) and subsequent development by gentle warming with a heat-gun. Purifications were performed by flash column chromatography using silica gel from Silicycle (60 Å, 40–63 µm) with the indicated eluent.
60 f254 precoated plates
Manufactured by Merck Group
Sourced in Germany
The 60 F254 precoated plates are a type of thin-layer chromatography (TLC) plate used for separating and analyzing chemical compounds. The plates are pre-coated with a silica gel 60 F254 adsorbent layer, which allows for the visualization of separated compounds under ultraviolet light.
Automatically generated - may contain errors
Lab products found in correlation
Silica gel 60, by Merck Group (3 mentions)
Mercury vx 300 spectrometer, by Agilent Technologies (2 mentions)
Zorbax sb c18 column, by Agilent Technologies (2 mentions)
Icr ftms apex 2, by Bruker (2 mentions)
2525 binary gradient module, by Agilent Technologies (2 mentions)
Elite lachrom instrument, by Hitachi (2 mentions)
Avance 300, by Bruker (1 mentions)
Micromass zq instrument, by Waters Corporation (1 mentions)
Amx 500, by JEOL (1 mentions)
Lcq xp, by Thermo Fisher Scientific (1 mentions)
Ft ir fts 135, by Bio-Rad (1 mentions)
Av 400, by Bruker (1 mentions)
Jnm eca600, by JEOL (1 mentions)
U 3000, by Hitachi (1 mentions)
Silica gel, by Merck Group (1 mentions)
Drx 300, by Bruker (1 mentions)
Drx 400, by Bruker (1 mentions)
Micromass q tof mass spectrometer, by Waters Corporation (1 mentions)
8 protocols using 60 f254 precoated plates
1
Synthesis of Organic Compounds under Inert Conditions
2
Spectroscopic Characterization of Organic Compounds
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1H NMR and 13C NMR were recorded on a Bruker Avance 300 (1H: 300 MHz, 13C: 75.46 MHz) spectrometer using residual CHCl3 as an internal reference (7.26 ppm) and at 293 K unless otherwise indicated. The chemical shifts (δ) and coupling constants (J) are expressed in ppm and Hz. The following abbreviations were used to explain the multiplicities: s = singlet, d = doublet, t = triplet, q = quartet and m = multiplet. Fourier transform infrared (FT-IR) spectra were recorded on a PerkinElmer FT spectrometer Spectrum two (UATR two). For electrospray ionization (ESI) high-resolution mass spectrometry (HRMS) analyses, a Waters Micromass ZQ instrument equipped with an electrospray source was used in the positive and/or negative mode. Matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometric analyses were performed on a PerSeptive Biosystems Voyager-De Pro MALDI mass spectrometer in the linear mode using 3,4-dihydroxybenzoic acid as the matrix. Analytical thin-layer chromatography was performed using silica gel 60 F254 precoated plates (Merck) with visualization by ultraviolet light, potassium permanganate, or sulfuric acid. Flash chromatography was performed on a silica gel (0.043–0.063 mm).
3
Synthesis of Compounds 1 and 2
4
Thin Layer Chromatography and Flash Chromatography
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TLC was used to monitor the evolution of the extent of the reaction by using silica gel 60 F254 precoated plates (E. Merck, Darmstadt, Germany). The individual compounds with aromatic groups were visualized using UV light (λ = 254 nm). For compounds without aromatic groups, the TLC plate was stained with iodine vapor to help visualization. Purification via flash column chromatography (SiO2) was performed using silica gel from Silicycle (60 Å, 40–63 μm), with the eluent partially mentioned in the experimental part for each compound. More details are available in previous publications from our laboratory [24 (link),25 (link),26 (link)].
5
NMR and HPLC Characterization Protocol
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All commercially available reagents and solvents were used without further purification.
NMR spectra were recorded on a Varian Mercury 300 VX spectrometer in CD3OD, CDCl3 or DMSO‐d6; chemical shifts were reported in ppm (δ). Peaks were assigned with 2D COSY experiments and agree with the proposed structures.
TLC analyses were carried out on Merck precoated 60 F254 plates using UV light and dipping with or a 10 % w/v ethanolic solution of ninhydrin.
Organic phases were dried over anhydrous sodium sulphate. Concentrations were performed under diminished pressure (1–2 kPa) at a bath temperature of 40 °C.
Flash column chromatography was performed using silica gel 60 (0.040–0.063 mm, Merck).
ESI‐HRMS were recorded on an ICR‐FTMS APEX II (Bruker Daltonics) mass spectrometer.
Preparative HPLC purifications were performed using CH3CN/H2O+CF3COOH gradient and a Waters 2525 Binary Gradient Module equipped with an Agilent Zorbax SB‐C18 column.
Purities of final compounds were determined by HPLC using CH3CN/H2O+CF3COOH gradient and a Purospher RP18 5 μm column on a Hitachi Elite Lachrom Instrument equipped with a DAD detector.
NMR spectra were recorded on a Varian Mercury 300 VX spectrometer in CD3OD, CDCl3 or DMSO‐d6; chemical shifts were reported in ppm (δ). Peaks were assigned with 2D COSY experiments and agree with the proposed structures.
TLC analyses were carried out on Merck precoated 60 F254 plates using UV light and dipping with or a 10 % w/v ethanolic solution of ninhydrin.
Organic phases were dried over anhydrous sodium sulphate. Concentrations were performed under diminished pressure (1–2 kPa) at a bath temperature of 40 °C.
Flash column chromatography was performed using silica gel 60 (0.040–0.063 mm, Merck).
ESI‐HRMS were recorded on an ICR‐FTMS APEX II (Bruker Daltonics) mass spectrometer.
Preparative HPLC purifications were performed using CH3CN/H2O+CF3COOH gradient and a Waters 2525 Binary Gradient Module equipped with an Agilent Zorbax SB‐C18 column.
Purities of final compounds were determined by HPLC using CH3CN/H2O+CF3COOH gradient and a Purospher RP18 5 μm column on a Hitachi Elite Lachrom Instrument equipped with a DAD detector.
6
Analytical Characterization of Synthesized Compounds
7
Optimization of Organic Synthesis Procedures
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All reactions were carried out in oven-dried glassware and dry solvents under nitrogen atmosphere. Unless otherwise stated, all solvents were purchased from Sigma Aldrich and used without further purification. Substrates and reagents were purchased from Sigma Aldrich and used as received. Thin-layer chromatography (TLC) was performed on Merck precoated 60F254 plates. Reactions were monitored by TLC on silica gel, with detection by UV light (254 nm) or by charring with 1% permanganate solution. Flash chromatography was performed using silica gel (240–400 mesh, Merck). 1H-NMR spectra were recorded on Bruker DRX-400 and Bruker DRX-300 instruments and are reported relative to residual CDCl3. {1H}13C-NMR spectra were recorded on the same instruments (101 and 75 MHz) and are reported relative to CDCl3. Chemical shifts (δ) for proton and carbon resonances are quoted in parts per million (ppm) relative to tetramethylsilane (TMS), which was used as an internal standard. MS spectra were recorded using an electrospray ionization (ESI) technique on a Waters Micromass Q-Tof mass spectrometer.
8
Optimized Synthetic Protocols for Novel Compounds
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All commercially available solvents and reagents were used without further purification, unless otherwise stated. NMR spectra were recorded on a Varian Mercury 300 VX spectrometer in CDCl3, CD3OD or DMSO-d6 and chemical shifts were reported in ppm (δ). Peaks were assigned with 2D COSY experiments and are in agreement with the proposed structures. TLC was carried out on Merck precoated 60 F254 plates using UV light and dipping with ethanol/phosphomolybdic acid 10% or a 10% w/v ethanolic solution of ninidrine. Flash column chromatography was performed using silica gel 60 (0.040-0.063 mm, Merck). Organic phases were dried over anhydrous sodium sulphate. Concentrations were performed under diminished pressure (1-2 kPa) at a bath temperature of 40 °C. ESI -HRMS were recorded on a ICR-FTMS APEX II (Bruker Daltonics) mass spectrometer. Preparative HPLC purifications were performed using CH3CN/H2O + CF3COOH gradient and a Waters 2525 Binary Gradient Module equipped with a Agilent Zorbax SB-C18 column. Purities of final compounds were determined by HPLC using CH3CN/H2O + CF3COOH gradient and a Purospher RP18 5 μm column on a Hitachi Elite Lachrom Instrument equipped with a DAD detector.
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