203854-59-5|(S)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-3-methylbutanoic acid| Ambeed

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Quality Control of [ 203854-59-5 ] Purity: 99% SDS Specification

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Product Details of [ 203854-59-5 ]

CAS No. :	203854-59-5
Formula :	C₂₁H₂₃NO₄
M.W :	353.41
SMILES Code :	CC(C)[C@@H](CNC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)C(O)=O
MDL No. :	MFCD07372881
InChI Key :	WVHQNPPGMKCPTP-GOSISDBHSA-N
Pubchem ID :	56971825

Safety of [ 203854-59-5 ]

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

Computational Chemistry of [ 203854-59-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	26
Num. arom. heavy atoms	12
Fraction Csp3	0.33
Num. rotatable bonds	8
Num. H-bond acceptors	4.0
Num. H-bond donors	2.0
Molar Refractivity	99.59
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	75.63 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.49
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.92
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.88
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.0
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.55
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.37

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.31
Solubility	0.0171 mg/ml ; 0.0000485 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-5.21
Solubility	0.00219 mg/ml ; 0.00000621 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.71
Solubility	0.000689 mg/ml ; 0.00000195 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.67 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<3.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.87

Application In Synthesis of [ 203854-59-5 ]

* 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 [ 203854-59-5 ]

[ 203854-59-5 ] Synthesis Path-Downstream 1~14

1
[ 82911-69-1 ]
[ 203854-54-0 ]
[ 203854-59-5 ]

References: [1]Helvetica Chimica Acta,1998,vol. 81,p. 187 - 206.
[2]Tetrahedron Asymmetry,2008,vol. 19,p. 2839 - 2849.
[3]Journal of Organic Chemistry,2003,vol. 68,p. 1575 - 1578.
[4]Chemistry and biodiversity,2012,vol. 9,p. 2494 - 2506.

2
[ 203854-58-4 ]
[ 203854-59-5 ]
[ 193887-45-5 ]
[ 203854-62-0 ]
(S)-β²-homovalyl-(S)-β²-homoalanyl-(S)-β²-homoleucyl-(S)-β²-homophenylalanyl-(S)-β²-homovalyl-(S)-β²-homoalanyl-(S)-β²-homoleucine [ No CAS ]

References: [1]Helvetica Chimica Acta,1998,vol. 81,p. 187 - 206.

3
(S)-3-Amino-7-(2-chloro-benzyloxycarbonylamino)-heptanoic acid benzyl ester; compound with trifluoro-acetic acid [ No CAS ]
[ 203854-59-5 ]
[ 888966-29-8 ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 361 - 403.

4
[ 941292-84-8 ]
[ 203854-59-5 ]

References: [1]Journal of the American Chemical Society,2011,vol. 133,p. 4246 - 4249.

5
[ 903889-49-6 ]
[ 203854-59-5 ]

References: [1]Journal of the American Chemical Society,2011,vol. 133,p. 4246 - 4249.

6
C₂₁H₂₅NO₃ [ No CAS ]
[ 203854-59-5 ]

References: [1]Journal of the American Chemical Society,2011,vol. 133,p. 4246 - 4249.

7
[ 71989-31-6 ]
[ 86123-10-6 ]
[ 109425-55-0 ]
[ 193887-44-4 ]
[ 203854-59-5 ]
C₇₄H₁₁₈N₁₂O₁₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Loading of the HMPB-MBHA-resin: The HMPB-MBHA-resin (theoretical loading=1.2 mmol/g, 2 mmol, 1.67 g) was suspended in 1,2-dichloroethane (10 mL) and concentrated thrice. Then a solution of the first amino acid (5 equiv, 10 mmol), DIC (5 equiv, 10 mmol, 1.54 mL), and DMAP (0.01 equiv, 20 mumol, 3 mg) in dry DCM/DMF (50 mL, 10:1 v/v) was added. The mixture was shaken for 3 h and then drained, washed subsequently with DCM, NMP, DCM, and Et2O. The resin was dried before determination of the loading. The loading procedure was repeated when the loading of the resin was found to be too low.Stepwise elongation: Fmoc-DPhe-HMPB-MBHA-resin (loading of the resin was 0.50 mmol/g, 100 mumol, 200 mg) was submitted to nine cycles of Fmoc solid-phase synthesis with the appropriate commercial amino acid building blocks, or Fmoc-beta2hVal-OH. The side chain of ornithine is protected with a Boc-group. Fmoc removal was effected by treatment with 20% piperidine in NMP for 2×10 min. The resin was subsequently washed with NMP, DCM, MeOH, and finally NMP. Fmoc-AA-OH (2.5 equiv, 250 mumol), HCTU (2.5 equiv, 250 mumol, 103 mg) in NMP was pre-activated for 1 min after the addition of DiPEA (3 equiv, 300 mumol, 53 muL) and then added to the resin. The suspension was shaken for 1.5 h. The resin was washed with NMP, DCM, MeOH, and NMP.Cleavage from the resin: After the final Fmoc deprotection the resin was washed with NMP and DCM and treated with 5 mL 1% TFA in DCM (6×10 min). The filtrates were collected, diluted with toluene (15 mL), and concentrated under reduced pressure. The residue was coevaporated with toluene (2×50 mL).Cyclization: In DMF (80 mL) were dissolved PyBOP (5 equiv, 500 mumol, 260 mg), HOBt (5 equiv, 500 mumol, 77 mg), and DiPEA (15 equiv, 1.5 mmol, 262 muL). The linear decapeptide was dissolved in DMF (5 mL) and added dropwise over 1 h to the reaction mixture. After addition the mixture was stirred for 16 h. The reaction mixture was concentrated in vacuo and the crude mixture was subjected to LH-20 size exclusion chromatography.Boc deprotection: The peptide was dissolved in DCM (2 mL) and TFA (2 mL) was added. The mixture was stirred for 2 h, concentrated, and coevaporated with toluene (2×10 mL). The obtained crude product was applied to preparative HPLC purification. Using gradients of aqueous TFA and acetonitrile the cyclic peptides 1-13 were obtained in the yield range 20-45%.

References: [1]Tetrahedron,2012,vol. 68,p. 2391 - 2400.

8
[ 71989-31-6 ]
[ 86123-10-6 ]
[ 109425-55-0 ]
[ 193887-44-4 ]
[ 203854-59-5 ]
(2R)-2-([(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl)-3-methylbutanoic acid [ No CAS ]
C₇₄H₁₁₆N₁₂O₁₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Loading of the HMPB-MBHA-resin: The HMPB-MBHA-resin (theoretical loading=1.2 mmol/g, 2 mmol, 1.67 g) was suspended in 1,2-dichloroethane (10 mL) and concentrated thrice. Then a solution of the first amino acid (5 equiv, 10 mmol), DIC (5 equiv, 10 mmol, 1.54 mL), and DMAP (0.01 equiv, 20 mumol, 3 mg) in dry DCM/DMF (50 mL, 10:1 v/v) was added. The mixture was shaken for 3 h and then drained, washed subsequently with DCM, NMP, DCM, and Et2O. The resin was dried before determination of the loading. The loading procedure was repeated when the loading of the resin was found to be too low.Stepwise elongation: Fmoc-DPhe-HMPB-MBHA-resin (loading of the resin was 0.50 mmol/g, 100 mumol, 200 mg) was submitted to nine cycles of Fmoc solid-phase synthesis with the appropriate commercial amino acid building blocks, or Fmoc-beta2hVal-OH. The side chain of ornithine is protected with a Boc-group. Fmoc removal was effected by treatment with 20% piperidine in NMP for 2×10 min. The resin was subsequently washed with NMP, DCM, MeOH, and finally NMP. Fmoc-AA-OH (2.5 equiv, 250 mumol), HCTU (2.5 equiv, 250 mumol, 103 mg) in NMP was pre-activated for 1 min after the addition of DiPEA (3 equiv, 300 mumol, 53 muL) and then added to the resin. The suspension was shaken for 1.5 h. The resin was washed with NMP, DCM, MeOH, and NMP.Cleavage from the resin: After the final Fmoc deprotection the resin was washed with NMP and DCM and treated with 5 mL 1% TFA in DCM (6×10 min). The filtrates were collected, diluted with toluene (15 mL), and concentrated under reduced pressure. The residue was coevaporated with toluene (2×50 mL).Cyclization: In DMF (80 mL) were dissolved PyBOP (5 equiv, 500 mumol, 260 mg), HOBt (5 equiv, 500 mumol, 77 mg), and DiPEA (15 equiv, 1.5 mmol, 262 muL). The linear decapeptide was dissolved in DMF (5 mL) and added dropwise over 1 h to the reaction mixture. After addition the mixture was stirred for 16 h. The reaction mixture was concentrated in vacuo and the crude mixture was subjected to LH-20 size exclusion chromatography.Boc deprotection: The peptide was dissolved in DCM (2 mL) and TFA (2 mL) was added. The mixture was stirred for 2 h, concentrated, and coevaporated with toluene (2×10 mL). The obtained crude product was applied to preparative HPLC purification. Using gradients of aqueous TFA and acetonitrile the cyclic peptides 1-13 were obtained in the yield range 20-45%.

References: [1]Tetrahedron,2012,vol. 68,p. 2391 - 2400.

9
[ 1415986-79-6 ]
[ 203854-59-5 ]