71989-33-8|(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)propanoic acid| Ambeed

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Quality Control of [ 71989-33-8 ] Purity: 98% SDS Specification

COA

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NMR

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CNMR

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Product Details of [ 71989-33-8 ]

CAS No. :	71989-33-8
Formula :	C₂₂H₂₅NO₅
M.W :	383.44
SMILES Code :	O=C(O)[C@H](COC(C)(C)C)NC(OCC1C2=CC=CC=C2C3=CC=CC=C13)=O
MDL No. :	MFCD00037127
InChI Key :	REITVGIIZHFVGU-IBGZPJMESA-N
Pubchem ID :	2724633

Safety of [ 71989-33-8 ]

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

Computational Chemistry of [ 71989-33-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	28
Num. arom. heavy atoms	12
Fraction Csp3	0.36
Num. rotatable bonds	9
Num. H-bond acceptors	5.0
Num. H-bond donors	2.0
Molar Refractivity	105.52
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	84.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.45
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	3.52
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.79
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.	2.41
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	3.35
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.11

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.16
Solubility	0.0266 mg/ml ; 0.0000695 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.	-4.99
Solubility	0.00396 mg/ml ; 0.0000103 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	-5.82
Solubility	0.000587 mg/ml ; 0.00000153 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	No
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	No
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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.14 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)	4.25

Application In Synthesis of [ 71989-33-8 ]

* 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 [ 71989-33-8 ]

[ 71989-33-8 ] Synthesis Path-Downstream 1~38

1
[ 35661-39-3 ]
[ 122889-11-6 ]
[ 71989-33-8 ]
AcNHSerSer(OBn)AlaCONH₂ [ No CAS ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 1691 - 1697.

2
[ 35661-39-3 ]
[ 122889-11-6 ]
[ 71989-33-8 ]
[ 849063-77-0 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 1691 - 1697.

3
[ 2439-37-4 ]
[ 103478-62-2 ]
[ 71989-33-8 ]
[ 77128-73-5 ]
(S)-2-[((S)-2-[(S)-3-tert-Butoxy-2-((S)-2-dimethylamino-4-methyl-pentanoylamino)-propionyl]-methyl-amino}-4-methyl-pentanoyl)-methyl-amino]-3-phenyl-propionic acid [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 3339 - 3344.

4
[ 2439-37-4 ]
[ 103478-62-2 ]
[ 71989-33-8 ]
[ 77128-73-5 ]
[ 873951-99-6 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 3339 - 3344.

5
[ 29022-11-5 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 108-24-7 ]
[ 198561-07-8 ]
Ac-Ser-Asp-Phe-Gly-OH [ No CAS ]

References: [1]Organic Letters,2007,vol. 9,p. 2469 - 2472.

6
Fmoc-Rink resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-33-8 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₁₇₅H₂₁₄N₂₁O₂₄PolS₃ [ No CAS ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14625 - 14633.

7
Fmoc-Rink resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-33-8 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 96402-49-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₁₃₁H₁₇₆N₁₉O₂₂PolS [ No CAS ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14625 - 14633.

8
C₃₃H₃₄N₃O₅Pol [ No CAS ]
[ 29022-11-5 ]
[ 35661-39-3 ]
[ 122889-11-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 71989-35-0 ]
[ 109425-51-6 ]
His-Ala-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Ser(OBn)-[2-amino-3-(biphenyl-4-yl)propanoyl]-NH₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7788 - 7799.

9
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 71989-16-7 ]
[ 91000-69-0 ]
[ 198561-07-8 ]
C₅₇H₉₃N₁₇O₂₂ [ No CAS ]

References: [1]Organic Letters,2011,vol. 13,p. 5604 - 5607.

10
[ 35661-39-3 ]
[ 51419-59-1 ]
[ 71989-33-8 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 1308685-69-9 ]

References: [1]Protein and Peptide Letters,2010,vol. 17,p. 1300 - 1304.

11
Fmoc-Asp(otBu)-Wang resin [ No CAS ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 120791-76-6 ]
[ 198561-07-8 ]
[ 684270-46-0 ]
C₁₃₅H₁₈₂N₁₈O₂₃S₃ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 7753 - 7762.

12
C₂₃H₂₂NO₆Pol [ No CAS ]
C₁₇H₃₅NO₅Si [ No CAS ]
[ 35661-60-0 ]
[ 132327-80-1 ]
[ 77128-73-5 ]
[ 71989-33-8 ]
[ 56-40-6 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
N-FMOC-O-tert-butyl-D-threonine [ No CAS ]
Fmoc-D-Ile-OH [ No CAS ]
C₇₅H₁₁₆N₂₀O₂₀ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 1556 - 1560.
Angew. Chem.,2015,vol. 127,p. 1576 - 1580,5.

13
[ 68858-20-8 ]
[ 71989-31-6 ]
[ 71989-33-8 ]
[ 96402-49-2 ]
C₂₆H₃₃N₄O₆Pol [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 11778 - 11782.
Angew. Chem.,2014,vol. 126,p. 11972 - 11976,5.

14
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
DCLGA-(L-1-naphthylalanyl)-RKCIPDNDKCCRPNLVCSRTHKWCKYVF-NH₂; disulfide linked (C2→C17, C9→C23, C16→C30) [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2299 - 2314.

15
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 71989-28-1 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
DCLGF-(L-1-naphthylalanyl)-RKCIPDNDKCCRPNLVCSRTHKWCKYVF-NH₂; disulfide linked (C2→C17, C9→C23, C16→C30) [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2299 - 2314.

16
fmoc-Leu-Alko Resin [ No CAS ]
[ 10147-11-2 ]
[ 29022-11-5 ]
[ 71989-33-8 ]
[ 96402-49-2 ]
[ 188970-92-5 ]
C₃₆H₄₅N₉O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solution of piperidine (1 mL) in anhydrous DMF (2 mL) and DCM (2 mL) was added to the peptide vessel containing the swelled resin (0.1 mmol). The mixture was allowed to rock for 30 minutes at room temperature. The solution was drained, and the resin was rinsed with DMF (3 mL x 2). A solution of 1:1 DCM/DMF (3 mL x 2) was added to the resin and the peptide vessel was allowed to rock for 3 minutes. The solution was drained, and DMF (3 mL) was added. The vessel was rocked for 3 minutes, and the solvent was drained. General procedure for peptide synthesis:1 Fmoc-amino acid (0.5 mmol), HOBT (0.068 g, 0.5 mmol), and HBTU (0.190 g, 0.5 mmol) were dissolved in anhydrous DMF (3 mL) and DCM (1 mL). DIEA (0.087 mL, 0.5 mmol) was added and the resulting solution was added to the peptide vessel containing the resin (0.1 mmol). The vessel was allowed to rock for 3 hours at room temperature, the solution was drained, and the resin was rinsed with DMF (3 mL x 2). A solution of 1:1 DCM/DMF (3 mL x 2) was added to the resin and the peptide vessel was allowed to rock for 3 minutes. The solution was drained, and DMF (3 mL) was added. The vessel was rocked for 3 minutes, and the solvent was drained. The resin 5 (0.05 mmol) was suspended in anhydrous DCM (3 mL) in a peptide vessel. Pd(PPh3)4 (0.046 g, 0.04 mmol) and phenylsilane (0.12 mL, 1.0 mmol) were added. The vessel was allowed to rock for 2 hours, and the solution was drained under vacuum. The resin was rinsed with DCM (3 mL x 2), followed by washing the resin with DCM (3 mL x 2) by rocking for 3 minutes. Generation of the side chain primary amine to generate resin-bound peptide 6 was confirmed by orange resin coloration upon testing with TNBS. Sodium azide (39 mg, 0.6 mmol) was dissolved in water (1 mL). Toluene (1 mL) was added and the solution was cooled to 0°C. Trifluoromethanesulfonic anhydride (Tf2O, 0.05 mL, 0.3 mmol) was added dropwise to the solution. The reaction mixture was stirred at 0°C for 30 minutes, followed by warming to room temperature and was stirred for 4 hours at room temperature. A saturated sodium carbonate solution was added until the reaction mixture became basic, and the organic layer was separated. The aqueous layer was extracted with toluene (2 mL x 3) and organic layers were combined. To the combined organic layers were added triethyl amine (0.02 mL, 0.15 mmol) and methanol (2 mL). The solution was transferred to the fritted vessel containing resin charged with peptide 6 (0.1 mmol). Solid zinc chloride (2.7 mg, 0.02 mmol) was then added and the mixture was rocked for 12 hours. The peptide was rinsed with DCM/DMF (1:1, 5 mL x 3) and solvent was drained under vacuum. The conversion of amine 6 to azide 7 was confirmed by the negativeTNBS test result, with the resin exhibiting a pale gray color. CuI (0.248 g, 1.3 mmol), ascorbic acid (0.228 g, 1.3 mmol) and DIEA (0.3 mL, 1.7 mmol) were dissolved in DMF (2.5 mL) and pyridine (1.5 mL). The solution was poured into the peptide vessel containing resin charged with azide peptide 7 (0.1 mmol). The appropriate substituted alkyne (0.3 mmol) was dissolved in DMF (1 mL) and transferred to the peptide vessel. Thepeptide vessel was rocked for 12 hours at room temperature. The obtained resin-bound crude products were rinsed with DMF (5 mL x 2), DMF/DCM (5 mL x 2), and DMF (5 mL) for 3 minutes for each rinse, with solvent drained under vacuum after each rinse. The resin-bound peptide 8 (0.05 mmol) was deprotected and cleaved from the resin support per previously reported protocols.1 The Fmoc group was removed according to the general procedure for Fmoc-deprotection described above. Following Fmoc removal, a cleavage cocktail of TFA/H2O/TIPS/anisole (4.5 mL/0.25 mL/0.125 mL/0.125 mL) was added to the vessel, and the vessel was allowed to rock for 3 hours. The solution was collected, and the resin was rinsed with TFA (1 mL x 2) with the rinse added to the collected solution. Ice cold ether (10 mL) was added to a separatory funnel. The combined cleavage solution was poured into the funnel, followed by 5percent acetic acid in water (5 mL). The resulting organic layer was extracted with 5percent acetic acid in water (5 mL x 3). The aqueous layer and washes were combined and the remaining TFA and acetic acid were removed under reduced pressure. The triazole peptide product 8 was obtained by lyophilization, and for initial screening was dissolved in DMSO and used without further purification.

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2800 - 2803.

17
[ 1026023-54-0 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 556-08-1 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 109425-51-6 ]
[ 116821-47-7 ]
[ 198561-07-8 ]
[ 334918-39-7 ]
C₁₂₈H₂₁₈N₅₀O₃₆ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 5273 - 5278.

18
[ 35661-60-0 ]
[ 35661-51-9 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 108-24-7 ]
[ 71989-38-3 ]
[ 132388-59-1 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
Ac-Tyr-Asn-Trp-Asn-Ser-Phe-azaGly-Leu-Arg-Tyr-NH₂ [ No CAS ]