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[ CAS No. 27144-18-9 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 27144-18-9
Chemical Structure| 27144-18-9
Structure of 27144-18-9 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 27144-18-9 ]

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Product Details of [ 27144-18-9 ]

CAS No. :27144-18-9 MDL No. :MFCD00237291
Formula : C22H20O2S Boiling Point : -
Linear Structure Formula :(C6H5)3CSCH2CH2CO2H InChI Key :AECGEIVNZGQBJT-UHFFFAOYSA-N
M.W : 348.46 Pubchem ID :262767
Synonyms :
Chemical Name :3-(Tritylthio)propanoic acid

Calculated chemistry of [ 27144-18-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.14
Num. rotatable bonds : 7
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 104.05
TPSA : 62.6 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.89
Log Po/w (XLOGP3) : 5.05
Log Po/w (WLOGP) : 5.08
Log Po/w (MLOGP) : 4.81
Log Po/w (SILICOS-IT) : 5.15
Consensus Log Po/w : 4.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.25
Solubility : 0.00195 mg/ml ; 0.00000559 mol/l
Class : Moderately soluble
Log S (Ali) : -6.11
Solubility : 0.000273 mg/ml ; 0.000000783 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -7.74
Solubility : 0.00000641 mg/ml ; 0.0000000184 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.27

Safety of [ 27144-18-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335-H413 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 27144-18-9 ]

* 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 [ 27144-18-9 ]

[ 27144-18-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 908846-88-8 ]
  • [ 27144-18-9 ]
  • [ 29022-11-5 ]
  • [ 112883-29-1 ]
  • [ 71989-14-5 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • 9-fluorenylmethoxycarbonyl-Nim-trityl-L-histidine [ No CAS ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • C61H75F2N15O13S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g-1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 0.5M HATU in DMF, 4eq of 2M DIPEA (double coupling for Tyr). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. (0835) The sequence of Fmoc protected amino acids and building blocks used are: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine (0836) 2. (S)-1 ((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid (0837) 3. (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tyrosine (0838) 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine (0839) 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid (0840) 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid (0841) 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid (0842) 8. (((9H-fluoren-9-yl)methoxy)carbonyl)glycine (0843) 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine (0844) 10.3-(tritylthio)propanoic acid (0845) At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5% H2O, 4% TIPS) for approximately 1.5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (399mg), which was used as crude in the next step. LCMS anal calcd. C61 H75F2N15013S2: 1328.48, found: 1328.2 (M+1 )+
  • 2
  • [ 908846-88-8 ]
  • [ 27144-18-9 ]
  • [ 71989-14-5 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • [ 35661-38-2 ]
  • 9-fluorenylmethoxycarbonyl-Nim-trityl-L-histidine [ No CAS ]
  • [ 77128-72-4 ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • C63H79F2N15O13S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g-1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 1 M Oxyme in DMF, 4eq of 0.5M L/,/V-diisopropylcarbodiimide (DIC) (double coupling for Y01 ). Fmoc deprotection cycles were performed using 20% (VA/) piperidine in DMF. (0856) The sequence of Fmoc protected amino acids and building blocks used are: (0857) 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1 ((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2 -carboxylic acid (0858) 3. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-methoxyphenyl)propanoic acid (0859) 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine (0860) 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid (0861) 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid (0862) 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid (0863) 8. (((9H-fluoren-9-yl)methoxy)carbonyl)-D-alanine (0864) 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine (0865) 10.3-(tritylthio)propanoic acid (0866) At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5% H2O, 4% TIPS) for approximately 1.5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (300mg), which was used as crude in the next step. (0867) LCMS anal calcd. C63H79F2N15013S2: 1356.53, found: 1356.9 (M+1 )+
  • 3
  • [ 908846-88-8 ]
  • [ 27144-18-9 ]
  • [ 29022-11-5 ]
  • N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine [ No CAS ]
  • [ 112883-29-1 ]
  • [ 71989-14-5 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • C61H75F2N15O13S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 0.5M HATU in DMF, 4eq of 2M DIPEA (double coupling for Tyr). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. (0284) The sequence of Fmoc protected amino acids and building blocks used were: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid 3. (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tyrosine 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid 8. (((9H-fluoren-9-yl)methoxy)carbonyl)glycine 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine 10. 3-(tritylthio)propanoic acid At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5% H2O, 4% TIPS) for approximately 1.5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (399mg), which was used as crude in the next step. LCMS analysis was calculated for C61 H75F2N15013S2: 1328.48, found: 1328.2 (M+1)+
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/iBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 0.5M HATU in DMF, 4eq of 2M DIPEA (double coupling for Tyr). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. (0775) The sequence of Fmoc protected amino acids and building blocks used were: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1 ((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid 3. (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tyrosine 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid 8. (((9H-fluoren-9-yl)methoxy)carbonyl)glycine 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine 10. 3-(tritylthio)propanoic acid At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5% H20, 4% TIPS) for approximately 1 .5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (399mg), which was used as crude in the next step. LCMS analysis was calculated for C61 H75F2N15013S2: 1328.48, found: 1328.2 (M+1 )+
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 0.5M HATU in DMF, 4eq of 2M DIPEA (double coupling for Tyr). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. The sequence of Fmoc protected amino acids and building blocks used were: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid 3. (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tyrosine 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid 8. (((9H-fluoren-9-yl)methoxy)carbonyl)glycine 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine 10. 3-(tritylthio)propanoic acid At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et2
  • 4
  • [ 908846-88-8 ]
  • [ 27144-18-9 ]
  • N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine [ No CAS ]
  • [ 71989-14-5 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • [ 35661-38-2 ]
  • [ 77128-72-4 ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • C63H79F2N15O13S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 1 M Oxyme in DMF, 4eq of 0.5M A/,//-diisopropylcarbodiimide (DIC) (double coupling for Y01). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. The sequence of Fmoc protected amino acids and building blocks used were: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid 3. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-methoxyphenyl)propanoic acid 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid 8. (((9H-fluoren-9-yl)methoxy)carbonyl)-D-alanine 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine 10. 3-(tritylthio)propanoic acid At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et2 H2O, 4% TIPS) for approximately 1.5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (300mg), which was used as crude in the next step. LCMS analysis was calculated for C63H79F2N15013S2: 1356.53, found: 1356.9 (M+1)+.
  • 5
  • [ 908846-88-8 ]
  • [ 27144-18-9 ]
  • [ 29022-11-5 ]
  • [ 112883-29-1 ]
  • [ 71989-14-5 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • 9-fluorenylmethoxycarbonyl-Nim-trityl-L-histidine [ No CAS ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • C61H75F2N15O13S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 0.5M HATU in DMF, 4eq of 2M DIPEA (double coupling for Tyr). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. The sequence of Fmoc protected amino acids and building blocks used were:1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid3. (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tyrosine4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid8. (((9H-fluoren-9-yl)methoxy)carbonyl)glycine9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine10. 3-(tritylthio)propanoic acidAt the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5%H2O, 4% TIPS) for approximately 1.5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (399mg), which was used as crude in the next step. LCMS analysis was calculated for C61 H75F2N15013S2: 1328.48, found: 1328.2 (M+1)+
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