[ CAS No. 71989-18-9 ]

Name: 71989-18-9|Fmoc-Glu(OtBu)-OH|98%
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{[proInfo.proName]} (Synonyms:(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid) ,{[proInfo.pro_purity]}

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Quality Control of [ 71989-18-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 71989-18-9 ]

SDS Specification

Alternatived Products of [ 71989-18-9 ]

Product Details of [ 71989-18-9 ]

CAS No. :	71989-18-9	MDL No. :	MFCD00037135
Formula :	C₂₄H₂₇NO₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OTKXCALUHMPIGM-FQEVSTJZSA-N
M.W :	425.47	Pubchem ID :	2724637
Synonyms :	(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid

Calculated chemistry of [ 71989-18-9 ]

Physicochemical Properties

Num. heavy atoms :	31
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.38
Num. rotatable bonds :	11
Num. H-bond acceptors :	6.0
Num. H-bond donors :	2.0
Molar Refractivity :	115.34
TPSA :	101.93 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.19
Log Po/w (XLOGP3) :	3.85
Log Po/w (WLOGP) :	4.1
Log Po/w (MLOGP) :	2.77
Log Po/w (SILICOS-IT) :	3.74
Consensus Log Po/w :	3.53

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.46
Solubility :	0.0146 mg/ml ; 0.0000344 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.69
Solubility :	0.000875 mg/ml ; 0.00000206 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.13
Solubility :	0.000314 mg/ml ; 0.000000738 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	4.35

Safety of [ 71989-18-9 ]

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

Application In Synthesis of [ 71989-18-9 ]

* 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.

Upstream synthesis route of [ 71989-18-9 ]
Downstream synthetic route of [ 71989-18-9 ]

[ 71989-18-9 ] Synthesis Path-Upstream 1~12

1
[ 71989-18-9 ]
[ 2419-56-9 ]

Reference： [1] Patent: WO2011/19942, 2011, A2, . Location in patent: Page/Page column 31-32
[2] Chemical Communications, 2015, vol. 51, # 78, p. 14624 - 14627

2
[ 71989-18-9 ]
[ 56-86-0 ]
[ 2419-56-9 ]

Reference： [1] Amino Acids, 2014, vol. 46, # 2, p. 367 - 374

3
[ 56-86-0 ]
[ 102774-86-7 ]
[ 115-11-7 ]
[ 84793-07-7 ]
[ 71989-18-9 ]
[ 129460-14-6 ]

Reference： [1] Synthesis, 1990, # 7, p. 571 - 572

4
[ 71989-18-9 ]
[ 104091-09-0 ]

Reference： [1] Tetrahedron Letters, 1992, vol. 33, # 37, p. 5441 - 5444
[2] Organic Letters, 2012, vol. 14, # 24, p. 6346 - 6349

5
[ 851713-96-7 ]
[ 71989-18-9 ]

Reference： [1] Organic Letters, 2005, vol. 7, # 8, p. 1473 - 1475

6
[ 2419-56-9 ]
[ 82911-69-1 ]
[ 71989-18-9 ]

Reference： [1] Synthetic Communications, 2009, vol. 39, # 11, p. 2022 - 2031
[2] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 11, p. 2189 - 2191
[3] European Journal of Organic Chemistry, 2015, vol. 2015, # 17, p. 3767 - 3770

7
[ 2419-56-9 ]
[ 88744-04-1 ]
[ 71989-18-9 ]

Reference： [1] Synthesis, 1986, # 4, p. 303 - 305

8
[ 2419-56-9 ]
[ 102774-86-7 ]
[ 71989-18-9 ]

Reference： [1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098

9
[ 56-86-0 ]
[ 102774-86-7 ]
[ 115-11-7 ]
[ 84793-07-7 ]
[ 71989-18-9 ]
[ 129460-14-6 ]

Reference： [1] Synthesis, 1990, # 7, p. 571 - 572

10
[ 71989-18-9 ]
[ 122350-52-1 ]

Reference： [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2958 - 2969
[2] Journal of Organic Chemistry, 1994, vol. 59, # 4, p. 929 - 931

11
[ 71989-18-9 ]
[ 144120-54-7 ]

Reference： [1] Tetrahedron Letters, 1993, vol. 34, # 10, p. 1549 - 1552
[2] Tetrahedron Letters, 1993, vol. 34, # 10, p. 1549 - 1552
[3] Tetrahedron Letters, 1992, vol. 33, # 32, p. 4557 - 4560
[4] Chemistry - A European Journal, 2015, vol. 21, # 25, p. 9249 - 9255

12
[ 71989-18-9 ]
[ 153815-59-9 ]

Reference： [1] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5260 - 5266
[2] Patent: US6747050, 2004, B1, . Location in patent: Page/Page column 37-38
[3] Organic Letters, 2015, vol. 17, # 3, p. 640 - 643
[4] ACS Combinatorial Science, 2017, vol. 19, # 3, p. 131 - 136

[ 71989-18-9 ] Synthesis Path-Downstream 1~68

1
[ 122889-11-6 ]
[ 71989-18-9 ]
[ 35737-15-6 ]
[ 35661-38-2 ]
Cbz-His-OH [ No CAS ]
(R)-4-{(R)-2-Benzyloxy-1-[(R)-1-((S)-1-carbamoyl-ethylcarbamoyl)-2-(1H-indol-3-yl)-ethylcarbamoyl]-ethylcarbamoyl}-4-[(R)-2-benzyloxycarbonylamino-3-(1H-imidazol-4-yl)-propionylamino]-butyric acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 192 - 200

2
[ 71989-18-9 ]
Fmoc-Leu-OH [ No CAS ]
[ 145038-49-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2795 - 2798

3
C₃₄H₂₈N₂O₇ [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 122889-11-6 ]
[ 71989-31-6 ]
[ 71989-18-9 ]
[ 103213-32-7 ]
[ 86060-81-3 ]
[ 116611-64-4 ]
[ 223416-45-3 ]

Yield	Reaction Conditions	Operation in experiment
		Chelmical synthesis: Peptides were synthesized on a Rink amide resin, 0.45 mmol/g [Fmoc-Cys(Trityl)-Wang; Novabiochem, San Diego, Calif.] usinig N-(9-fluorenyl)methoxycarboxyl chemistry and standard side chain protection except on cysteine residues. Cysteine residues were protected in pairs with either S-trityl on the first and third cysteines or S-acetamidomethyl on the second and fourth cysteines. Amino acid derivatives were from Advanced Chemtech (Louisville, Ky.). The peptides were removed from the resin and precipitated, and a two-step oxidation protocol was used to selectively fold the peptides as described previously (Luo et al., 1999). Briefly, the first disulfide bridge was closed by dripping the peptide into an equal volume of 20 mM potassium feliicyanide and 0.1 M Tris, pH 7.5. The solution was allowed to react for 30 min, and the monocyclic peptide was purified by reverse-phase HPLC. Simultaneous removal of the S-acetamidomethyl groups and closure of the second disulfide bridge was carried out by iodine oxidation. The monocyclic peptide and HPLC eluent was dripped into an equal volume of iodine (10 mM) in H20/trifluoroacetic acid/acetonitrile (78:2:20 by volume) and allowed to react for 10 min. The reaction was terminated by the addition of ascorbic acid diluted 20-fold with 0.1percent trifluoroacetic acid and the bicyclic product purified by HPLC. Mass Spectrometry: Measurements were performed at the Salk Institute for Biological Studies (San Diego, Calif.) under the direction of Jean Rivier. Matrix-assisted laser desorption ionization time-of-flight mass spectrometry and liquid secondary ionization mass spectrometry were used.

Reference： [1]Patent: US2006/211623,2006,A1 .Location in patent: Page/Page column 9

4
[ 2799-07-7 ]
[ 71989-31-6 ]
[ 71989-18-9 ]
[ 71989-23-6 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 1127631-92-8 ]

Reference： [1]Chemical Communications,2009,p. 407 - 409

5
[ 35661-60-0 ]
[ 71989-18-9 ]
[ 135673-97-1 ]
[ 162558-25-0 ]
Fmoc-4-bromo-L-phenylalanine [ No CAS ]
N-[(9-fluorenyl)methoxycarbonyl]-4-chloro-L-phenylalanine [ No CAS ]
[ 1186310-41-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 5229 - 5237

6
[ 35661-40-6 ]
[ 71989-18-9 ]
[ 125238-99-5 ]
[ 135673-97-1 ]
N-[(9-fluorenyl)methoxycarbonyl]-4-chloro-L-phenylalanine [ No CAS ]
[ 1186310-44-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 5229 - 5237

7
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 ]

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

8
[ 90-34-6 ]
[ 71989-18-9 ]
[ 1267638-91-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With diisopropyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 4h;	General procedure: To an ice cooled stirred solution of 8-quinolinamine (1 or 3, 0.37 mmol) and orthogonally protected amino acid (0.41 mmol) in anhydrous CH2Cl2 (10 mL), DIC (0.41 mmol) was added. The reaction mixture was allowed to attain room temperature and stirring continued for another 4 h. The solvent was removed yielding the crude product. Purified by column chromatography on silica gel (100-200 mesh) using 0.7-1.2% CH3OH in CH2Cl2 to afford 45-49 as oil.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 197 - 210

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 ]

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

10
aminomethylpolystyrene [ No CAS ]
[ 1204595-05-0 ]
[ 71989-18-9 ]
[ 68858-21-9 ]
N^α-Fmoc-Arg(N^g-Pbf)-OH [ No CAS ]
C₈₇H₁₄₂N₃₉O₁₇Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Solid phase peptide synthesis (0.1 mmol scale) based on Fmoc protection strategy was performed on aminomethylated polystyrene resin (1.0 mmol/g) derivatised with HMP linker, the attachment of which is described in method A. Coupling of the first residue was performed according to method B and the level of first residue attachment was estimated using the UVmethod. The peptide chain was then assembled using a Tribute peptide synthesiser (ProteinTechnologies, Inc.) (method C) and the peptide was capped manually with D-biotin according to method D and cleaved from resin according to method E. Method A: attachment of HMP linker to aminomethylated PS resin Aminomethylated resin (0.1 mmol) was swollen in DCM/DMF (1:1) for 20 min and then the solvents were drained. HMP (3 eq) and HOBt (3,8 eq) were dissolved in 3 mL of 20% DMF in DCM and DIC (3 eq) was added. The reaction mixture was added to the resin and agitated for 2 h. The mixture was drained and the resin washed with DMF (3 x) and DCM (3 x). Method B: first residue attachment The Fmoc protected C-terminal amino acid (4 eq) was dissolved in 3 mL of 20% DMF in DCM. DIC (5 eq) was added and the reaction mixture added to HMP resin. DMAP (1/10 eq in 122 muL of DMF) was added and the mixture agitated for 1.5 h. The mixture was drained and the resin washed with DMF (3 x) and DCM (3 x). Method C: automated Fmoc SPPS, Tribute peptide synthesiser Couplings of Fmoc-Glu and Fmoc-Arg (5 eq) were carried out in 45 min at room temperature inthe presence of HBTU (4.6 eq) and NMM (10 eq) in DMF. The Nalpha-protecting group was removed by 20% piperidine solution in DMF (3 mL, 2 x 5 min). Method D: biotin attachment D-biotin (4 eq), BOP (4 eq) and HOBt (4 eq) were suspended in 3 mL of DMF. After addition of DIPEA (8 eq) the mixture was added to the resin and agitated for 2 h at rt followed by washing with DMF (3 x) and DCM (3 x). Method E: cleavage from resin/side-chain deprotection 100 muL TIPS, 250 muL H2O, 250 muL 3,6-dioxa-1,8-octanedithiol and 9.4 mL TFA were added to the resin and the mixture was agitated for 2 h at room temperature. The TFA solution was filtered and the peptide precipitated by addition of hexane/diethyl ether (1:1). After centrifugation and washing with hexane/diethyl ether (1:1) the crude peptide was lyophilisedfrom 0.1% trifluoroacetic acid-water.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 2638 - 2644

11
[ 35661-39-3 ]
[ 1356004-85-7 ]
[ 71989-18-9 ]
[ 71989-26-9 ]
[ 198561-07-8 ]
[ 1421510-90-8 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 4540 - 4542

12
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 71989-35-0 ]
[ 71989-28-1 ]
[ 72040-64-3 ]
Fmoc-L-Arg(PG)-OH, PG = protecting group [ No CAS ]
Fmoc-L-His(PG)-OH, PG = protecting group [ No CAS ]
[N-(biotinyl)-6-aminocaproyl]-LSPLGEEMRDRARAHVDALRT-NH₂ [ No CAS ]