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Chemical Structure| 302941-52-2 Chemical Structure| 302941-52-2
Chemical Structure| 302941-52-2

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Product Details of DUPA

CAS No. :302941-52-2
Formula : C11H16N2O9
M.W : 320.25
SMILES Code : O=C(N[C@@H](CCC(O)=O)C(O)=O)N[C@@H](CCC(O)=O)C(O)=O
English Name :(2S,2'S)-2,2'-(Carbonylbis(azanediyl))dipentanedioic acid
MDL No. :MFCD27949023

Safety of DUPA

Application In Synthesis of DUPA

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 302941-52-2 ]

[ 302941-52-2 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 16859-12-4 ]
  • [ 302941-52-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In ethyl acetate; <i>tert</i>-butyl alcohol
  • 2
  • [ 2791-84-6 ]
  • [ 302941-52-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / -78 °C 2: Et3N / CH2Cl2 / -78 - 20 °C 3: H2 / 20percent Pd(OH)2/C / 2-methyl-propan-2-ol; ethyl acetate
  • 3
  • [ 302941-54-4 ]
  • [ 302941-52-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / -78 - 20 °C 2: H2 / 20percent Pd(OH)2/C / 2-methyl-propan-2-ol; ethyl acetate
  • 4
  • [ CAS Unavailable ]
  • [ 302941-52-2 ]
  • [ 3064483-62-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C70H103N6O18Pol With piperidine In N,N-dimethyl-formamide Stage #2: 2-[3-(1,3-dicarboxypropyl)ureido]pentanedioic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Stage #3: With triisopropylsilane; trifluoroacetic acid In water for 0.416667h; Inert atmosphere; 2.C Synthesis of DUPA-(PEG)12-EDA: Synthesis of DUPA-(PEG)12-EDA: 1,2-Diaminoethane trityl-resin (0.025 g) was loaded into a peptide synthesis vessel and washed with i-PrOH (3 x 10 mL), followed by DMF (3 x lOmL). To the vessel was then introduced a solution of Fmoc-NH-(PEG)12-COOH (42.8 mg) in DMF, i-Pr2NEt (2.5 equiv), and PyBOP (2.5 equiv). The resulting solution was bubbled with Ar for 1 h, the coupling solution was drained, and the resin washed with DMF (3 x 10 mL) and iPrOH (3 x 10 mL). Kaiser tests were performed to assess reaction completion. Fmoc deprotection was carried out using 20% piperidine in DMF (3 x 10 mL). This procedure was repeated to complete the all coupling steps (2 x 1.5 equiv of Fmoc-Phe-OH and 1.5 equiv of 8- aminooctanoic acid and 1.2 equiv of DUPA were used on each of their respective coupling steps). After the DUPA coupling, the resin was washed with DMF (3 x 10 mL) and i-PrOH (3 x 10 mL) and dried under reduced pressure. The peptide was cleaved from the resin in the peptide synthesis vessel using a cleavage mixture consisting of 95% CF3CO2H, 2.5% H20, and 2.5% triisopropylsilane. Fifteen milliliters of the cleavage mixture was added to the peptide synthesisSynthesis of DUPA-(PEG)12-EDA:
  • 5
  • [ CAS Unavailable ]
  • [ 1002-57-9 ]
  • [ 35661-40-6 ]
  • [ 302941-52-2 ]
  • [ 1952360-91-6 ]
  • [ 3064483-62-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1,2-diaminoethane trityl resin; 3-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy ]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; isopropyl alcohol Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: 8-Aminooctanoic acid; N-Fmoc L-Phe; 2-[3-(1,3-dicarboxypropyl)ureido]pentanedioic acid Further stages; 6 Synthesis of FITC-PEGl 2-DUPA 1,2-Diaminoethane trityl-resin (0.025 g) was loaded into a peptide synthesis vessel and washed with i-PrOH (3 x 10 mL), followed by DMF (3 x lOmL). To the vessel was then introduced a solution of Fmoc-NH-(PEG)i2-COOH (42.8 mg) in DMF, i-PnNEt (2.5 equiv), and PyBOP (2.5 equiv). The resulting solution was bubbled with Ar for 1 h, the coupling solution was drained, and the resin washed with DMF (3 x 10 mL) and i-PrOH (3 x 10 mL). Kaiser tests were performed to assess reaction progress. Fmoc deprotection was carried out using 20% piperidine in DMF (3 x 10 mL). This procedure was repeated to complete the all coupling steps (2 x 1.5 equiv of Fmoc- Phe-OH and 1.5 equiv of 8-aminooctanoic acid and 1.2 equiv of DUPA were used on each of their respective coupling steps).[0232] After the DUPA coupling, the resin was washed with DMF (3 x 10 mL) and i-PrOH (3 x 10 mL) and dried under reduced pressure. The peptide was cleaved from the resin in the peptide synthesis vessel using the Cleavage Solution. 15 mL of the Cleavage Solution was added to the peptide synthesis vessel, and the reaction was bubbled under Ar for 15 min. The resin was treated with two additional 10 mL quantities of the Cleavage Solution for 5 min each. The cleavage mixture was concentrated to about 5 mL and precipitated with ethyl ether. The precipitate was collected by centrifugation, washed with ethyl ether (3X), and dried under high vacuum, resulting in the recovery of crude material.
  • 6
  • [ 2206660-96-8 ]
  • [ 302941-52-2 ]
YieldReaction ConditionsOperation in experiment
66% With trifluoroacetic acid In dichloromethane at 20℃; 1 Synthesis of DUPA Add 544 mg of tBuDUPA to a 100 mL three-necked flask, add 1 mL of dichloromethane to dissolve, add 1 mL of trifluoroacetic acid, stir at room temperature to react, and monitor the disappearance of the raw material by LC-MS. Add 50 mL of ether, and a large amount of white solid precipitates. Filter and wash the filter cake twice with 50 mL of ether. Dry to obtain 210 mg of white solid. Yield 66%.
  • 7
  • [ 16874-06-9 ]
  • [ 302941-52-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice 2: trifluoroacetic acid / dichloromethane / 20 °C
 

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