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Chemical Structure| 122350-52-1 Chemical Structure| 122350-52-1

Structure of Fmoc-Glu-Obzl
CAS No.: 122350-52-1

Chemical Structure| 122350-52-1

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Product Details of [ 122350-52-1 ]

CAS No. :122350-52-1
Formula : C27H25NO6
M.W : 459.49
SMILES Code : [H][C@@](CCC(O)=O)(NC(=O)OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)C(=O)OCC1=CC=CC=C1
MDL No. :MFCD00080272
InChI Key :FMWLYDDRYGOYMY-DEOSSOPVSA-N
Pubchem ID :10049854

Safety of [ 122350-52-1 ]

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

Application In Synthesis of [ 122350-52-1 ]

* 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 [ 122350-52-1 ]

[ 122350-52-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 122350-52-1 ]
  • [ 1791-13-5 ]
  • Fmoc-Glu{Asp(OtBu)-OtBu}-OBzl [ No CAS ]
  • 2
  • [ 35661-39-3 ]
  • [ 1427040-55-8 ]
  • [ 122889-11-6 ]
  • [ 71989-23-6 ]
  • [ 122350-52-1 ]
  • (6S,9S,12S,15S)-6-{(S)-3-amino-3-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propanamido}-15-(benzyloxymethyl)-12-sec-butyl-9-methyl-3,7,10,13-tetraoxo-1-phenyl-2-oxa-8,11,14-triazahexadecan-16-oic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% The peptide 4 was synthesized manually on an activated 2-chlorotrityl chloride resin (1 g) which had been swelled in dry DCM for 30 min. The first amino acid Fmoc-Ser-OH was coupled to the resin using dry DCM (10 mL) and DIPEA (6.65 mmol) for 2 h under a N2 atmosphere. Resin substitution was 0.6 mol g?1 as determined by the Fmoc UV assay. The Fmoc group of serine was removed using 20 percent piperidine in DMF (3 × 10 mL) for30 min. Subsequently, amino acids Fmoc-Ile-OH, Fmoc-Ala-OH,and Fmoc-Glu-OH (0.20 mM) were coupled using DIPEA (1 mM) and HCTU (0.50 mM) in DMF. The Fmoc group of glutamic acid was removed using 20 percent piperidine in DMF (3 ×10 mL) for 30 min and finally sugar amino acid 1 was coupled using DIPEA (1 mM) and HCTU (0.50 mM) in DMF. Standardwashing procedures were used. Cleavage from the resin was performed, using a cleavage mixture of 5 percent TFA in DCM (3 ×10 mL)for 30 min. The crude compound was then purified usingsemi-preparative HPLC on a Shimadzu Instrument LC-8A (AceC18 150 mm × 21.2 mm × 5 mm) with an UV/VIS detector SPD-M20A (215nmand 254 nm) and automated fraction collector FRC-10a with 15mLmin?1 flow rate and two buffer system waterand MeOH containing 0.1 percent HCOOH with method RP-HPLC:5 percent MeOH /95 percent H2O/0.1 percent HCOOH to 95 percent MeOH /5 percentH2O/0.1 percent HCOOH in 35 min. Compound 4 was obtained in 64 percent yield as a white solid, mp 171 °C.
 

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