Ferulic acid (99%) and triphenyl phosphine (99%) were purchased from Sigma-Aldrich Japan Co., Ltd. p-Coumaric acid (>98.0%), sinapinic acid (>98.0%), oxalyl chloride (>98.0%), and diisopropyl azodicarboxylate (40% in toluene, ca. 1.9 mol L−1) were purchased from Tokyo Chemical Industry Co., Ltd. Methyl ricinoleate (>97.0%), acetic anhydride (>97.0%), N,N-dimethylaminopyridine (DMAP) (>99.0%), N,N′-diisopropylcarbodiimide (DIC) (>99.0%), pyridine (>99.5%, dehydrated), N,N-dimethylformamide (DMF) (>99.5%, dehydrated), sodium sulphate (Na2SO4) (>99.0%), and tetrahydrofuran (THF) (>99.5%, with stabilizer, for gel permeation chromatography (GPC) grade) were purchased from FUJIFILM Wako Pure Chemical Corporation. p-Toluenesulfonic acid monohydrate (>99.0%) and lithium hydroxide monohydrate (>99.0%) were purchased from KISHIDA CHEMICAL Co., Ltd. Toluene (>99.5%, dehydrated), dichloromethane (CH2Cl2) (>99.5%, dehydrated), and THF (>99.5%, dehydrated stabilizer free) were purchased from Kanto Chemical and purified on a Glass Contour Solvent Purification System (NIKKO HANSEN & Co., Ltd, Japan). Chloroform-d1 (99.8 atom % D with 0.03 vol% tetramethylsilane) was purchased from Kanto Chemical. These chemicals were used without further purification unless otherwise noted. 4-(Dimethylamino)pyridinium p-toluenesulfonate (DPTS) was synthesised according to the literature.43 (link)
Diisopropyl azodicarboxylate
Manufactured by Merck Group
Sourced in Germany
Diisopropyl azodicarboxylate is a chemical compound used as a reagent in organic synthesis. It functions as an oxidizing agent and is commonly employed in various chemical reactions, such as Mitsunobu reactions. The compound is available as a laboratory product for research and development purposes.
Automatically generated - may contain errors
Lab products found in correlation
Triphenylphosphine, by Merck Group (3 mentions)
Tetrahydrofuran, by Merck Group (2 mentions)
Dichloromethane, by Thermo Fisher Scientific (2 mentions)
Oxalyl chloride, by Merck Group (1 mentions)
Methyl ricinoleate, by Tokyo Chemical Industry (1 mentions)
Acetic anhydride, by Tokyo Chemical Industry (1 mentions)
Pyridine, by Fujifilm (1 mentions)
Sinapinic acid, by Merck Group (1 mentions)
Tetrahydrofuran thf, by Fujifilm (1 mentions)
N n diisopropylcarbodiimide dic, by Fujifilm (1 mentions)
Dichloromethane ch2cl2, by Kanto Chemical (1 mentions)
Chloroform d1, by Kanto Chemical (1 mentions)
N n dimethylformamide (dmf), by Fujifilm (1 mentions)
P coumaric acid, by Merck Group (1 mentions)
Ferulic acid, by Merck Group (1 mentions)
Deuterated water, by Deutero (1 mentions)
Cholesterol, by Thermo Fisher Scientific (1 mentions)
Toluene, by Merck Group (1 mentions)
Thionyl chloride, by Merck Group (1 mentions)
Furan, by Merck Group (1 mentions)
8 protocols using diisopropyl azodicarboxylate
1
Synthesis and Characterization of Ferulic Acid Esters
2
Synthesis of Multiarm PEG-Based Drug Conjugates
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The 5-fluorouracil (5-FU) was purchased from Applichem for Pharmaceuticals Co., GmbH (Darmstadt, Germany). Methotrexate (MTX) was obtained from Haupt Pharma Wolfratshausen GmbH (Chemajet Co., (Wolfratshausen, Bayern, Germany). β-Cyclodextrin (β-CD) and epichlorohydrin (EP) were obtained from Wacker Fine Chemicals (Wacker Chemie AG, Burghausen, Germany). Diisopropyl azodicarboxylate (DIAD), brine, Toluene, and succinic anhydride (SA) were delivered from Sigma-Aldrich (Schnelldorf, Germany). Cholesterol, triphenylphosphine (PPh3), phthalimide, dibutyltin dilaurate (DBDL), and dimethyl aminopropyl-ethyl carbodiimide (EDC) were obtained from Acros Organics (Geel, Belgium). Linear eight-armed poly (ethylene glycol) with a molecular weight of 20 kDa (8armPEG20k-OH) was delivered from Jenkem Technology (Beijing, China). Ethanol, tetrahydrofuran (THF), triethylamine (TEA) dichloromethane (DCM), and the other chemicals of an analytical grade were obtained from Merck KGaA (Darmstadt, Germany). Phosphate buffered saline (PBS), deuterated water, and chloroform (respectively, d6-D2O and d6-CDCl3) were purchased from Deutero (Kastellaun, Germany). Celite 503 were obtained from Fluka (Taufkirchen, Germany).
3
Synthesis of Functionalized Norbornene Derivatives
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Example 1
Materials: The following materials were purchased and used as received.
Dimethyl 5-norbornene-2,3-dicarboxylate (C3) was purchased from Alfa Aesar,
Dichloromethane (DCM) was stored over activated Alumina and purged with Argon before use, Isopropyl alcohol (IPA), dicyclopentadiene (DCPD), 1H,1H,2H-Perflouro-1-octene (PF6), 1H,1H,2H-Perflouro-1-dodecene (PF10), toluene, thionyl chloride, ethylacetate, dimethylformamide (DMF), Maleimide, furan, diisopropylazodicarboxylate (DIAD), triphenylphosphine (Ph3P), 1-haxadecanol, tetrahydrofuran (THF), ethyl acetate, N-phenylMaleimide, acetonitrile, methanol, Grubbs second generation catalyst, 3-bromopyridine, and pentane were obtained from Sigma-Aldrich Co. and used without further treatment. Dichloropentane, also obtained from Sigma-Aldrich Co., was treated with basic alumina before use. Cyclooctadiene (COD) was purified by vacuum distillation from boron trifluoride and used fresh.
4
Kraft Lignin Functionalization and Evaluation
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Kraft lignin (KL) was purchased from Sigma Aldrich (St. Louis, MO, USA) and used after purification by standard procedures including alkali–acid treatment and continuous washing with deionized water. Dimethyl isosorbide (DMI), ethanol, 2,2-diphenyl-1-picrylhydrazyl (DPPH), L-ascorbic acid AA, 3-O-ethylascorbate 1 , ferulic acid 2 , palmitic acid 3 , 6-O-Palmitoyl-L-ascorbic acid 6 , diisopropyl azodicarboxylate (DIAD), triphenylphosphine (TPP), butylhydroxytoluene (BHT), para-4-nitrophenyl laurate (para-NPL), chitosan (non-animal derived, average Mw 50 kDa, CH), concanavalin A (Con A, from Canavalia ensiformis, Jack bean type VI), and Lipase B from Candida antarctica were purchased from Sigma Aldrich and used without further purification. Analytical grade tetrahydrofuran THF and 2-methyl tetrahydrofuran (2-MeTHF) were refluxed over Na–benzophenone under nitrogen, followed by distillation and storage over 4 Å molecular sieves. Deuterated and HPLC purity-grade solvents were purchased from VWR. 1H and 13C NMR spectra were obtained in MeOD3 using a Bruker 400 MHZ spectrometer (Bruker, Billerica, MA, USA).
5
Fluorine-Containing Polymer Synthesis
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Benzotrifluoride, diisopropyl azodicarboxylate, maleimide, and anhydrous THF were purchased from Sigma-Aldrich and used as received. 1,1,1,2,3,3-Hexafluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)pentane (PF-7600) was bought from 3 M Korea and used without further purification. 2,2-Azobisisobutyronitrile (AIBN) was obtained from Junsei Chemical and used after recrystallization from a mixed solvent of MeOH and CHCl3. 4-Cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanoic acid (CDSTSP),48 (link) 5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-heptadecafluorododecan-1-ol,49 (link) and 5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-heptadecafluorododecan-1-amine50 (link) were prepared according to the literature.
6
Synthesis of Colloidal Nanocrystals
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Indium acetate [In(ac)3, 99.99%], zinc acetate [Zn(ac)2, 99.99%], chloroform-d (CDCl3, 99.8%, contains 0.03% TMS), diisopropyl azodicarboxylate (DIAD, 98%), trioctylamine (TOA, 98%), selenium (Se, 99.99%), sulfur (S, 99.98%), tetrahydrofuran (THF, 99.8%), hydrofluoric acid (HF, 48%), and trichloromethane-d1 (CDCl3, 99.9%, contains 0.5 wt% silver foil as stabiliser) were purchased from Sigma-Aldrich. Oleic acid (OA, 99%), trioctylphosphine (PR’3, 97%), stearic acid (99%), nitrosonium tetrafluoroborate (NOBF4, 98%), N,N-dimethylformamide (DMF, 99.8%), 1-octadecene (ODE, 99%), and dichloromethand-d2 (CD2Cl2, 99.9%) were purchased from Alfa Aesar. Squalane was purchased from Acros Organics. Tris(trimethylsilyl)phosphine [(TMS)3P, 99.9%] was purchased from Uniam. All chemicals were used as received.
7
Synthesis of Furan-Based Polymer Hydrogels
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Furan, maleic anhydride, poly(ethylene glycol)
(Mw = 600, 1450, 4000); pentaerythritol
tetrakis(3-mercaptopropionate) (PETMP); 2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone;
1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) hydrochloride;
ethanol; N,N-dicyclohexylcarbodiimide
(DCC); 1,6-hexanediol; 4-dimethylaminopyridine (DMAP); triphenylphodphene
(PPh3); diisopropyl azodicarboxylate (DIAD); compound3 ;14 toluene; hexane; deuterated
chloroform (CDCl3); and deuterated dimethylsufoxide (DMSO-d6) were purchased from Sigma-Aldrich. Potassium
bicarbonate, sodium chloride, and sodium bicarbonate were purchased
from Merck and used without further purification. Dichloromethane
was distilled over calcium hydride under atmospheric pressure.
(Mw = 600, 1450, 4000); pentaerythritol
tetrakis(3-mercaptopropionate) (PETMP); 2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone;
1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) hydrochloride;
ethanol; N,N-dicyclohexylcarbodiimide
(DCC); 1,6-hexanediol; 4-dimethylaminopyridine (DMAP); triphenylphodphene
(PPh3); diisopropyl azodicarboxylate (DIAD); compound
chloroform (CDCl3); and deuterated dimethylsufoxide (DMSO-d6) were purchased from Sigma-Aldrich. Potassium
bicarbonate, sodium chloride, and sodium bicarbonate were purchased
from Merck and used without further purification. Dichloromethane
was distilled over calcium hydride under atmospheric pressure.
8
Synthesis and Characterization of PEGylated Maleimide Conjugates
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Anhydrous 1,4-dioxane, dichloromethane, sodium bicarbonate (NaHCO 3 ), sodium sulfate (Na 2 SO 4 ), and triphenylphosphine were purchased from Acros Organics (Geel, Belgium). Boc-6aminohexanoic acid was purchased from Bachem (Weil am Rhein, Germany). Diethyl ether was obtained from CSC Ja ¨cklechemie (Nuremberg, Germany). Eight-armed poly(ethylene glycol) with a molecular mass of 40 000 Da (8armPEG40k-OH) was purchased from JenKem Technology (Allen, TX, USA). Ceteareth-20 was obtained from Kolb Distribution Ltd (Hedingen, Switzerland). Acetyl chloride, 12-aminododecanoic acid, anhydrous dimethylformamide, anhydrous tetrahydrofuran, deuterated chloroform (CDCl 3 ), N,N 0 -dicyclohexylcarbodiimide (DCC), diisopropyl azodicarboxylate, N,N-diisopropylethylamine, di-tert-butyl dicarbonate, fluorescamine, 3-(2-furyl)propanoic acid, N-hydroxysuccinimide (NHS), N-methoxycarbonylmaleimide, piperidine, and pyrene were received from Sigma-Aldrich (Taufkirchen, Germany). All other chemicals were obtained from Merck KGaA (Darmstadt, Germany). Bevacizumab (Avastin s , 25 mg mL À1 , Roche Ltd, Basel, Switzerland) was kindly provided by the hospital pharmacy of the University of Regensburg (Germany). Purified water was freshly prepared using a Milli-Q water purification system (Millipore, Schwalbach, Germany).
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