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Chemical Structure| 756526-04-2 Chemical Structure| 756526-04-2
Chemical Structure| 756526-04-2

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NH2-PEG8-acid is a non-cleavable ADC linker containing 8 PEG units, suitable for synthesizing antibody-drug conjugates (ADCs). It also serves as a PROTAC linker, part of the PEG class, and can be used for synthesizing PROTAC molecules.

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Product Details of NH2-PEG8-acid

CAS No. :756526-04-2
Formula : C19H39NO10
M.W : 441.51
SMILES Code : O=C(O)CCOCCOCCOCCOCCOCCOCCOCCOCCN
MDL No. :MFCD11041146
InChI Key :YLKOHZCQTVYVDB-UHFFFAOYSA-N
Pubchem ID :51340929

Safety of NH2-PEG8-acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of NH2-PEG8-acid

* 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 [ 756526-04-2 ]

[ 756526-04-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 756526-04-2 ]
  • [ 1426827-79-3 ]
  • C30H51NO12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; water; at 20℃; for 1.5h; To a solution of H2N-PEG8-COOH (822 mg, 1.86 mmol) in THF:H20 1 : 1 (20 mL) were added BCN-OSu (23) (651 mg, 2.23 mmol) and Et3N (774 μ, 5.59 mmol). The reaction was stirred at r.t. for 1.5 h andd acidified to pH 1 followed by extraction with EtOAc (3 x 35 mL). The combined organic layers were dried over Na2S04, filtered and the solvent removed under reduced pressure. The crude product was then dissolved in dry DCM (20 mL) and subsequently DCC (461 mg, 2.23 mmol) and NHS (257 mg, 2.23 mmol) were added. After stirring at r.t. for 1 h, the reaction was filtered and the filtrate concentrated in vacuo. Flash chromatography (MeCN, MeCN:H20 30: 1) afforded BCN-PEG8-COOSu.1H-NMR (300 MHz, CDC13): δ 5.44 (br s, 1H), 4.14 )d, J= 8.1 Hz, 2H), 3.84 (t, J= 6.3 Hz, 2H), 3.68-3.63 (m, 30H), 3.56 (t, J = 5.2 Hz, 2H), 3.34 (q, J = 5.4 Hz, 2H), 2.90 (t, J = 6.3 Hz, 2H), 2.85 (s, 4H), 2.36-2.14 (m, 6H). 1.72-1.49 (m, 2H), 1.36 (qn, J = 8.7 Hz, 1H), 1.02-0.88 (m, 2H).LRMS (ESI+) calcd for C34H54N2Oi4(M+Na+) 737.35, found 737.3.
  • 2
  • [ 6066-82-6 ]
  • [ 756526-04-2 ]
  • [ 1426827-79-3 ]
  • [ 1608140-48-2 ]
YieldReaction ConditionsOperation in experiment
60% To a solution of amino-dPEG8-acid (217 mg, 0.492 mmol) in anhydrous DMF (3 mL) were subsequently added 51 (143 mg, 0.492 mmol) and Et3N (204 tL, 1.47 mmol). The reaction mixture stirred for 3h at rt, after which EDCI.HC1 (0.88 g, 4.61 mmol) and NHS (88 mg, 0.77 mmol) were added. The resulting solution was stirred overnight at rt andpoured into 50 mL NaHCO3 (sat.) and 50 mL EtOAc. The layers were separated and the organic phase was washed with sat. NaHCO3 (50 mL) and H20 (30 mL). The organic phase was dried (Na2504), filtered and concentrated in vacuo. Gradient flash chromatography (MeCN - MeCN:H20 30:1) afforded product 60b as colorless oil (212 mg, 0.30 mmol, 60%).‘H NMR (300 IVIFIz, CDC13): (ppm) 4.13 (d, J 8.1 Hz, 2H), 3.84 (t, J 6.3 Hz, 2H),3.68-3.59 (m, 28 H), 3.54 (t, J 5.1 Hz, 2H), 3.36 (q, J= 5.4 Hz, 2H), 2.89 (t, J= 6.3Hz, 2H), 2.82 (s, 4H), 2.35-2.15 (m, 6H), 1.68-1.48 (m, 2H), 1.44-1.23 (m, 1H), 1.00-0.86 (m, 2H). LRMS (ESI+) m/z calcd for C34H54N20,4 (M+Naj = 737.8; found 737.3.
 

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