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[ CAS No. 117666-96-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 117666-96-3
Chemical Structure| 117666-96-3
Structure of 117666-96-3 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 117666-96-3 ]

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Product Details of [ 117666-96-3 ]

CAS No. :117666-96-3 MDL No. :MFCD00151937
Formula : C31H25NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :SYOBJKCXNRQOGA-NDEPHWFRSA-N
M.W : 491.53 Pubchem ID :14233360
Synonyms :

Calculated chemistry of [ 117666-96-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 37
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.13
Num. rotatable bonds : 10
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 139.53
TPSA : 92.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.96
Log Po/w (XLOGP3) : 5.99
Log Po/w (WLOGP) : 5.45
Log Po/w (MLOGP) : 3.72
Log Po/w (SILICOS-IT) : 5.59
Consensus Log Po/w : 4.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -6.48
Solubility : 0.000162 mg/ml ; 0.00000033 mol/l
Class : Poorly soluble
Log S (Ali) : -7.71
Solubility : 0.0000095 mg/ml ; 0.0000000193 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -9.74
Solubility : 0.000000089 mg/ml ; 0.0000000002 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.11

Safety of [ 117666-96-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 117666-96-3 ]

* 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 [ 117666-96-3 ]

[ 117666-96-3 ] Synthesis Path-Downstream   1~45

  • 1
  • [ 117666-96-3 ]
  • [ 655224-07-0 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
68% With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane
  • 2
  • [ 110-89-4 ]
  • [ 425393-71-1 ]
  • [ CAS Unavailable ]
  • [ 117666-96-3 ]
  • [ 425393-79-9 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol In methanol; dichloromethane; water 62 2-Amino-3-(4-benzoyl-phenyl)-N-{3-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-pyridin-2-yl-ethyl]-benzyl}propionamide Example 62 2-Amino-3-(4-benzoyl-phenyl)-N-{3-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-pyridin-2-yl-ethyl]-benzyl}propionamide N-Fmoc-4-benzoylphenylalanine (1 mmol, 491 mg) was mixed with HOBT,H2O (1 mmol, 153 mg) in dichloromethane (20 mL); EDAC,HCl (1.1 mmol, 200 mg) was added and the mixture stirred under nitrogen at room temperature for 2 h. 3-[2-(4,5-Dihydro-1H-imidazol-2-yl)-1-pyridin-2-yl-ethyl]benzylamine (1 mmol, 280 mg) in dichloromethane (4 mL) was added and the mixture stirred overnight at room temperature. The solvent was subsequently evaporated and the residue treated with piperidine:methanol (1:4) (20 mL) by stirring at room temperature for 30 min. The solvent was evaporated and the residue extracted between NaOH (1 M) and dichloromethane. The organic layers were collected and evaporated to give an oil. Treatment with methanol caused crystallisation of Fmoc-piperidine, which was isolated by filtration and discarded. The filtrate was purified on a silica gel column yielding 2-amino-3-(4-benzoyl-phenyl)-N-{3-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-pyridin-2-yl-ethyl]benzyl}propionam ide (220 mg) as an oil. LCMS: m/z (M+1)+532. Retention time: 1.92 min, purity (ELS) 95%.
  • 3
  • [ 53293-00-8 ]
  • [ 88574-06-5 ]
  • 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
  • [ 185116-43-2 ]
  • [ 1011719-43-9 ]
  • 4
  • [ 53293-00-8 ]
  • [ 149834-58-2 ]
  • 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
  • [ 185116-43-2 ]
  • methyl-8-chloro-8-oxooctanoate [ No CAS ]
  • C44H54N4O7 [ No CAS ]
  • 5
  • [ 53293-00-8 ]
  • [ 164470-64-8 ]
  • 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
  • [ 1011719-33-7 ]
  • 6
  • [ 53293-00-8 ]
  • [ 164470-64-8 ]
  • 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
  • C30H28N2O5 [ No CAS ]
  • 7
  • [ 53293-00-8 ]
  • 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
  • [ 185116-43-2 ]
  • [ 1011719-39-3 ]
  • 8
  • [ 53293-00-8 ]
  • 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
  • [ 185116-43-2 ]
  • C29H26N2O5 [ No CAS ]
  • 9
  • [ 41624-92-4 ]
  • [ 102169-54-0 ]
  • 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
  • C31H38N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multistep reaction.;
  • 10
  • [ 41624-92-4 ]
  • [ 102169-54-0 ]
  • 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
  • [ 185116-43-2 ]
  • C38H43N3O6 [ No CAS ]
  • 11
  • [ CAS Unavailable ]
  • [ 117666-96-3 ]
  • [ 1124322-52-6 ]
YieldReaction ConditionsOperation in experiment
90% With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;
  • 13
  • [ CAS Unavailable ]
  • [ 117666-96-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine at 20℃; for 0.5h; solid phase reaction;
  • 14
  • [ CAS Unavailable ]
  • [ 117666-96-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; solid phase reaction;
  • 15
  • [ CAS Unavailable ]
  • [ 117666-96-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine at 20℃; for 0.5h; solid phase reaction;
  • 16
  • [ CAS Unavailable ]
  • [ 117666-96-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; solid phase reaction;
  • 17
  • [ CAS Unavailable ]
  • [ 117666-96-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol In N,N-dimethyl-formamide for 1.5h; solid phase reaction;
  • 18
  • [ 910297-59-5 ]
  • [ 117666-96-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
88.9% With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine at 20℃; Inert atmosphere;
  • 19
  • [ CAS Unavailable ]
  • [ 71989-28-1 ]
  • [ 117666-96-3 ]
  • [ 1960446-61-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C11H9N2O3Pol; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid With 2,4,6-trimethyl-pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine Further stages;
  • 20
  • [ 1229035-97-5 ]
  • [ 117666-96-3 ]
  • [ 1827586-65-1 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid With benzotriazol-1-ol; 1,2-dichloro-ethane In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; Molecular sieve; Inert atmosphere; Stage #2: 7a-(4-aminobutyl)-2-{4-[4-(1-naphthyl)piperazin-1-yl]butyl}tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione In dichloromethane at 20℃; for 72h; Inert atmosphere;
  • 21
  • [ 117666-96-3 ]
  • [ 1827586-66-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1,2-dichloro-ethane / N,N-dimethyl-formamide; dichloromethane / 1 h / 20 °C / Molecular sieve; Inert atmosphere 1.2: 72 h / 20 °C / Inert atmosphere 2.1: piperidine / dichloromethane / 2 h / 0 °C / Inert atmosphere 2.2: Inert atmosphere
  • 22
  • [ 117666-96-3 ]
  • [ 1827586-41-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: benzotriazol-1-ol; 1,2-dichloro-ethane / N,N-dimethyl-formamide; dichloromethane / 1 h / 20 °C / Molecular sieve; Inert atmosphere 1.2: 72 h / 20 °C / Inert atmosphere 2.1: piperidine / dichloromethane / 2 h / 0 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.2: 72 h / 20 °C / Inert atmosphere
  • 23
  • [ 117666-96-3 ]
  • [ 1916487-93-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 2: piperidine / dichloromethane / 20 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
  • 24
  • [ 117666-96-3 ]
  • [ 2035120-49-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 2: piperidine / dichloromethane / 20 °C / Inert atmosphere
  • 25
  • [ 117666-96-3 ]
  • [ 2035120-51-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 2: piperidine / dichloromethane / 20 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 4: dichloromethane / 12 h / 20 °C / Inert atmosphere
  • 26
  • [ 117666-96-3 ]
  • [ 1916487-96-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 2: piperidine / dichloromethane / 20 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 4: dichloromethane / 12 h / 20 °C / Inert atmosphere 5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; benzotriazol-1-ol / 1,4-dioxane / 12 h / 20 °C / Inert atmosphere
  • 27
  • [ CAS Unavailable ]
  • [ 117666-96-3 ]
  • [ 1916488-01-1 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere;
  • 28
  • [ 1918-77-0 ]
  • [ CAS Unavailable ]
  • [ 71989-31-6 ]
  • [ 35737-15-6 ]
  • [ 76-05-1 ]
  • [ 117666-96-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
25% Stage #1: Fmoc-L-Asn-OH With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 2h; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: Thiophene-2-acetic acid; Fmoc-Pro-OH; Fmoc-Trp-OH; trifluoroacetic acid; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid; Fmoc-Arg(pg)-OH
  • 29
  • [ 117666-96-3 ]
  • [ 2305312-92-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 0.5 h 1.2: 6 h / 20 °C 2.1: piperidine / dichloromethane / 0.5 h
  • 30
  • [ 117666-96-3 ]
  • [ 2305312-93-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 0.5 h 1.2: 6 h / 20 °C 2.1: piperidine / dichloromethane / 0.5 h 3.1: dichloromethane / 0.25 h / 20 °C
  • 31
  • [ 117666-96-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 0.5 h 1.2: 6 h / 20 °C 2.1: piperidine / dichloromethane / 0.5 h 3.1: dichloromethane / 0.25 h / 20 °C 4.1: aq. phosphate buffer / 20 °C / pH 7.2
  • 32
  • [ 117666-96-3 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane for 0.5h; Stage #2: Propargylamine In dichloromethane at 20℃; for 6h;
  • 33
  • [ 29022-11-5 ]
  • [ 35661-60-0 ]
  • [ 35661-40-6 ]
  • [ 71989-16-7 ]
  • [ 112667-29-5 ]
  • [ 73724-45-5 ]
  • [ 117666-96-3 ]
  • [ 58-85-5 ]
  • [ 2131089-40-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(9-fluorenylmethoxycarbonyl)-L-phenylalaninamide With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide Automated synthesizer; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; N-Fmoc L-Phe; Fmoc-Asn-OH; N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid; biotin; Fmoc-Arg(pg)-OH; Fmoc-Trp(pg)-OH Further stages; Peptide Synthesis General procedure: The different kisspeptin-10 peptides were synthesized by standard Fmoc-based solid-phase peptide synthesis on a Syro II automated peptide synthesizer (Multisyntech), using either Rink Amide AM (200-400 mesh) or Rink Amide ChemMatrix as solid support. The peptide chain was assembled using HBTU as coupling reagent. For Fmoc-deprotection, a 3′ treatment with 40% piperidine in DMF was used, followed by a 12′ treatment with 20% piperidine in DMF. The furan and benzophenone moiety were introduced using the commercially available unnatural amino acids Fmoc--(2-furyl)-Ala-OH and Fmoc-L-4-Benzoylphenylalanine-OH. These amino acids were coupled manually to the peptide chain using COMU as coupling reagent. (0386) All peptides were biotinylated after automated synthesis using either biotin or biotin-dPEG(4)-COOH, with COMU as coupling reagent in the presence of DIPEA. Peptides were cleaved off with TFA/TIS/H2O (95/2.5/2.5) during 2 h and precipitated with cold methyl tert-butyl ether and analysed by RP-HPLC and ESI-MS or MALDI-MS
  • 34
  • [ 29022-11-5 ]
  • [ 35661-60-0 ]
  • [ 35661-40-6 ]
  • [ 71989-16-7 ]
  • [ 112667-29-5 ]
  • [ 73724-45-5 ]
  • [ 117666-96-3 ]
  • [ 58-85-5 ]
  • [ 2131089-38-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(9-fluorenylmethoxycarbonyl)-L-phenylalaninamide With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide Automated synthesizer; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; N-Fmoc L-Phe; Fmoc-Asn-OH; N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid; biotin; Fmoc-Arg(pg)-OH; Fmoc-Tyr-O(*) Further stages; Peptide Synthesis General procedure: The different kisspeptin-10 peptides were synthesized by standard Fmoc-based solid-phase peptide synthesis on a Syro II automated peptide synthesizer (Multisyntech), using either Rink Amide AM (200-400 mesh) or Rink Amide ChemMatrix as solid support. The peptide chain was assembled using HBTU as coupling reagent. For Fmoc-deprotection, a 3′ treatment with 40% piperidine in DMF was used, followed by a 12′ treatment with 20% piperidine in DMF. The furan and benzophenone moiety were introduced using the commercially available unnatural amino acids Fmoc--(2-furyl)-Ala-OH and Fmoc-L-4-Benzoylphenylalanine-OH. These amino acids were coupled manually to the peptide chain using COMU as coupling reagent. (0386) All peptides were biotinylated after automated synthesis using either biotin or biotin-dPEG(4)-COOH, with COMU as coupling reagent in the presence of DIPEA. Peptides were cleaved off with TFA/TIS/H2O (95/2.5/2.5) during 2 h and precipitated with cold methyl tert-butyl ether and analysed by RP-HPLC and ESI-MS or MALDI-MS
  • 35
  • [ 29022-11-5 ]
  • [ 35661-60-0 ]
  • [ 35661-40-6 ]
  • [ 71989-14-5 ]
  • [ 108-24-7 ]
  • [ 71989-35-0 ]
  • [ 117666-96-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate for 0.75h; Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide Automated synthesizer; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; N-Fmoc L-Phe; Fmoc-(tBu)Asp-OH; acetic anhydride; Fmoc-Thr(tBu)-OH; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid; Fmoc-Glu(Pg)-OH Further stages; General procedure: The amino acids (5eq) were activated with equimolar amounts of HATU and a 2-fold molar excess of DIPEA and acylated for 45min over the resin free amino groups. Fmoc deprotection in each coupling step and the end of the linear assembly was performed with 20% piperidine in (DMF). Acetylation of the N-terminus was performed by treating the resin in DMF with acetic anhydride (10eq) for 15min. The dry peptide-resin was treated with the cleavage mixture, 92.5% TFA, 2.5% TIPS and 5% H2O for 1h at RT. The resin was filtered off, the volatiles were evaporated by SpeedVac and the peptide precipitated by addition of cold MTBE. After removal of the supernatant, the peptide pellets were washed twice with MTBE, dried, taken into ACN/H2O and lyophilized. Lyophilization afforded crude peptides in yields ranging between 80 and 90%. The overall purity of the crude peptide was >90% as assessed by UPLC-MS analysis (Column: C18 ACQUITY BEH 1.7µm, 2.1x100 mm, 100Å, gradient: 10%-10% (1.5min)-60% (4min)-80% (1min) %B where A=H2O+0.1%TFA and B=ACN+0.1%TFA). The crude peptides were purified by RP-HPLC on an automated Waters FractionLynx RP-HPLC/MS using a Waters XBridge BEH C18 OBD Prep Column (130Å, 5µm, 30mm×150mm) at a flow rate of 30mL/min, λ=214nm, with a 10-10% (5min)-60%(20min) %B linear gradient (A=H2O+0.1%TFA and B=ACN+0.1%TFA). Purified peptides were recovered by lyophilization of pooled fractions with a purity>95% and yields ranging between 35 and 55%.
  • 36
  • [ 68858-20-8 ]
  • [ 2624118-11-0 ]
  • [ CAS Unavailable ]
  • [ 114360-54-2 ]
  • [ 84624-17-9 ]
  • [ 76-05-1 ]
  • [ 117666-96-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: C20H20NO3Pol With morpholine; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: Fmoc-Val-OH With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #3: Fmoc-L-Thz-(L-Val)-OH; N-(9-fluorenylmethoxycarbonyl)-D-leucine; N-(9-fluorenylmethoxycarbonyl)-D-valine; trifluoroacetic acid; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid Further stages;
  • 37
  • (2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid [ No CAS ]
  • [ 6089-09-4 ]
  • [ 929-10-2 ]
  • [ 71989-35-0 ]
  • [ 125238-99-5 ]
  • 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid [ No CAS ]
  • [ 135112-27-5 ]
  • (2S)-2-[9H-fluorene-9-ylmethoxycarbonylamino]-4-methylsulfonylbutanoic acid [ No CAS ]
  • 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
  • C68H101N9O16S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: (2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: With piperidine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #3: 4-pentynoic acid; isooctanoic acid; Fmoc-Thr(tBu)-OH; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid; (2S)-2-[9H-fluorene-9-ylmethoxycarbonylamino]-4-methylsulfonylbutanoic acid; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid Further stages;
  • 38
  • (2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid [ No CAS ]
  • [ 6089-09-4 ]
  • [ 929-10-2 ]
  • [ 71989-35-0 ]
  • [ 125238-99-5 ]
  • 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid [ No CAS ]
  • [ 135112-27-5 ]
  • (2S)-2-[9H-fluorene-9-ylmethoxycarbonylamino]-4-methylsulfonylbutanoic acid [ No CAS ]
  • 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
  • C68H101N9O16S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: With piperidine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #3: (2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid; 4-pentynoic acid; isooctanoic acid; Fmoc-Thr(tBu)-OH; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid; (2S)-2-[9H-fluorene-9-ylmethoxycarbonylamino]-4-methylsulfonylbutanoic acid; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid Further stages;
  • 39
  • [ 235788-61-1 ]
  • [ 6089-09-4 ]
  • [ 929-10-2 ]
  • [ 35661-60-0 ]
  • [ 71989-35-0 ]
  • [ 114360-54-2 ]
  • [ 125238-99-5 ]
  • [ 130309-37-4 ]
  • [ 135112-27-5 ]
  • [ 163437-14-7 ]
  • [ 117666-96-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: Fmoc-Thr(tBu)-OH With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: With piperidine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #3: (2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid; 4-pentynoic acid; isooctanoic acid; Fmoc-Leu-OH; Fmoc-Thr(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-D-leucine; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid; (2S)-2-[9H-fluorene-9-ylmethoxycarbonylamino]-4-methylsulfonylbutanoic acid; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid Further stages;
  • 40
  • [ 235788-61-1 ]
  • [ 6089-09-4 ]
  • [ 929-10-2 ]
  • [ 35661-60-0 ]
  • [ 71989-35-0 ]
  • [ 114360-54-2 ]
  • [ 125238-99-5 ]
  • [ 130309-37-4 ]
  • [ 135112-27-5 ]
  • [ 163437-14-7 ]
  • [ 117666-96-3 ]
  • [ 2823428-20-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Fmoc-Thr(tBu)-OH With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: With piperidine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #3: (2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid; 4-pentynoic acid; isooctanoic acid; Fmoc-Leu-OH; Fmoc-Thr(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-D-leucine; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid; (2S)-2-[9H-fluorene-9-ylmethoxycarbonylamino]-4-methylsulfonylbutanoic acid; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid Further stages;
  • 41
  • [ 235788-61-1 ]
  • [ 6089-09-4 ]
  • [ 929-10-2 ]
  • [ 35661-60-0 ]
  • [ 71989-35-0 ]
  • [ 114360-54-2 ]
  • [ 125238-99-5 ]
  • [ 130309-37-4 ]
  • [ 135112-27-5 ]
  • [ 163437-14-7 ]
  • [ 117666-96-3 ]
  • [ 2823428-24-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Fmoc-Thr(tBu)-OH With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: With piperidine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #3: (2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid; 4-pentynoic acid; isooctanoic acid; Fmoc-Leu-OH; Fmoc-Thr(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-D-leucine; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid; (2S)-2-[9H-fluorene-9-ylmethoxycarbonylamino]-4-methylsulfonylbutanoic acid; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid Further stages;
  • 42
  • [ 235788-61-1 ]
  • [ 6089-09-4 ]
  • [ 71989-35-0 ]
  • [ 130309-37-4 ]
  • [ 135112-27-5 ]
  • [ 163437-14-7 ]
  • [ 117666-96-3 ]
  • [ 2823428-43-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Fmoc-Thr(tBu)-OH With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: With piperidine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #3: (2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid; 4-pentynoic acid; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid; (2S)-2-[9H-fluorene-9-ylmethoxycarbonylamino]-4-methylsulfonylbutanoic acid; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid Further stages;
  • 43
  • [ 235788-61-1 ]
  • [ 6089-09-4 ]
  • [ 71989-35-0 ]
  • [ 125238-99-5 ]
  • [ 130309-37-4 ]
  • [ 135112-27-5 ]
  • [ 163437-14-7 ]
  • [ 117666-96-3 ]
  • [ 2823428-39-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Fmoc-Thr(tBu)-OH With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: With piperidine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #3: (2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid; 4-pentynoic acid; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid; (2S)-2-[9H-fluorene-9-ylmethoxycarbonylamino]-4-methylsulfonylbutanoic acid; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid Further stages;
  • 44
  • [ 235788-61-1 ]
  • [ 6089-09-4 ]
  • [ 35661-60-0 ]
  • [ 71989-35-0 ]
  • [ 114360-54-2 ]
  • [ 125238-99-5 ]
  • [ 130309-37-4 ]
  • [ 135112-27-5 ]
  • [ 163437-14-7 ]
  • [ 117666-96-3 ]
  • [ 2823428-16-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Fmoc-Thr(tBu)-OH With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: With piperidine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #3: (2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid; 4-pentynoic acid; Fmoc-Leu-OH; N-(9-fluorenylmethoxycarbonyl)-D-leucine; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid; (2S)-2-[9H-fluorene-9-ylmethoxycarbonylamino]-4-methylsulfonylbutanoic acid; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid Further stages;
  • 45
  • [ 6089-09-4 ]
  • [ 130309-37-4 ]
  • [ 135112-27-5 ]
  • [ 163437-14-7 ]
  • [ 117666-96-3 ]
  • [ 2823427-84-3 ]
YieldReaction ConditionsOperation in experiment
16.7% Stage #1: (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine at 20℃; for 2h; Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #3: 4-pentynoic acid; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; (2S)-2-[9H-fluorene-9-ylmethoxycarbonylamino]-4-methylsulfonylbutanoic acid; 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid Further stages;
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