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Chemical Structure| 894095-98-8 Chemical Structure| 894095-98-8
Chemical Structure| 894095-98-8

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β-D-glucuronide-pNP-carbonate is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs)[1].

Synonyms: β-D-glucuronide-pNP-carbonate

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Product Details of β-D-glucuronide-pNP-carbonate

CAS No. :894095-98-8
Formula : C45H43N3O18
M.W : 913.83
SMILES Code : C(OC(NCCC(NC1=C(O[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](C(OC)=O)O2)C=CC(COC(OC3=CC=C(N(=O)=O)C=C3)=O)=C1)=O)=O)C4C=5C(C=6C4=CC=CC6)=CC=CC5
Synonyms :
β-D-glucuronide-pNP-carbonate
MDL No. :MFCD31715405
InChI Key :DMGQNZOORDYDEZ-LELKPENRSA-N
Pubchem ID :59816534

Safety of β-D-glucuronide-pNP-carbonate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of β-D-glucuronide-pNP-carbonate

* 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 [ 894095-98-8 ]

[ 894095-98-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 474645-27-7 ]
  • [ 894095-98-8 ]
  • (3S,4S,6S)-6-[2-(3-aminopropanoylamino)-4-[[[(1S)-1-[[(1S)-1-[[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]amino]-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl]-2-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]methylcarbamoyl]-2-methylpropyl]carbamoyl]-2-methylpropyl]methylcarbamoyl]oxymethyl]phenoxy]-3,4,5-trihydroxytetrahydropyran-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% Dissolve methyl (2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[2-[3-(9H-fluoren-9- ylmethoxycarbonylamino)propanoylamino]-4-[(4- nitrophenoxy)carbonyloxymethyl]phenoxy]tetrahydropyran-2-carboxylate (155mg, 0.17mmol) and (2S)-N-[(l S)-l-[[(l S,2R)-4-[(2S)-2-[(lR,2R)-3-[[(lR,2S)-2-hydroxy-l- methyl-2-phenyl-ethyl]amino]- 1 -methoxy-2-methyl-3-oxo-propyl]pyrrolidin- 1 -yl]-2- methoxy-l-[(l S)-l-methylpropyl]-4-oxo-butyl]-methyl-carbamoyl]-2-methyl-propyl]-3- methyl-2-(methylamino)butanamide (MMAE) (146 mg, 0.17 mmol) into DMF (2 mL) and add DIPEA (36 mu, 0.21 mmol) and HOBt (8 mg, 0.059 mmol) to the solution. Stir at room temperature overnight. Add MeOH (1 mL) and IN LiOH (1 mL). Concentrate and purify by HPLC (Column; Phenomenex Luna 5 muiotaeta CI 8 AXIA packed 30 x 75 mm column, Mobile phase; A: 0.1percent TFA in water, B: 0.1percent TFA in Acetonitrile, Monitored; 214 nm, Flow rate; 85 mL/min., Gradient; 10-38percent, Gradient time; 8 min.). Dry the collected fractions by lyophilizer to give the desired product, (3S,4S,6S)-6-[2-(3- aminopropanoylamino)-4-[[[(l S)-l-[[(l S)-l-[[(l S,2R)-4-[(2S)-2-[(lR,2R)-3-[[(lR,2S)-2- hydroxy- 1 -methyl -2-phenyl-ethyl]amino]-l -methoxy-2-methyl -3-oxo-propyl]pyrrolidin- l-yl]-2-methoxy-l-[(l S)-l-methylpropyl]-4-oxo-butyl]-methyl-carbamoyl]-2-methyl- propyl]carbamoyl]-2-methyl-propyl]-methyl-carbamoyl]oxymethyl]phenoxy]-3,4,5- trihydroxy-tetrahydropyran-2-carboxylic acid (NFb-P-Glucn-MMAE) (122 mg, Yield 64percent). MS m/z 1130 (M+H).
 

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