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Quality Control of [ 13726-84-6 ] Purity: 97% SDS Specification

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Product Details of [ 13726-84-6 ]

CAS No. :	13726-84-6
Formula :	C₁₄H₂₅NO₆
M.W :	303.35
SMILES Code :	O=C(OC(C)(C)C)CC[C@@H](C(O)=O)NC(OC(C)(C)C)=O
MDL No. :	MFCD00038257
InChI Key :	YGSRAYJBEREVRB-VIFPVBQESA-N
Pubchem ID :	6993432

Safety of [ 13726-84-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Calculated chemistry of [ 13726-84-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	21
Num. arom. heavy atoms	0
Fraction Csp3	0.79
Num. rotatable bonds	10
Num. H-bond acceptors	6.0
Num. H-bond donors	2.0
Molar Refractivity	77.02
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	101.93 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.48
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	1.72
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.09
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.	1.34
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	1.22
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.77

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.14
Solubility	2.18 mg/ml ; 0.00717 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.48
Solubility	0.101 mg/ml ; 0.000334 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-1.95
Solubility	3.4 mg/ml ; 0.0112 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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	No
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.	-6.93 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	1.0 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<1.0
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)	3.41

Application In Synthesis of [ 13726-84-6 ]

* 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 [ 13726-84-6 ]

[ 13726-84-6 ] Synthesis Path-Downstream 1~30

1
[ 130333-58-3 ]
[ 13726-84-6 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 1253 - 1256.

2
[ 13726-84-6 ]
[ 74-88-4 ]
(R)-2-tert-Butoxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1339 - 1346.

3
[ 13726-84-6 ]
[ 62-53-3 ]
[ 179083-21-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 511 - 514.

4
[ 13726-84-6 ]
[ 179082-63-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 511 - 514.

5
[ 13726-84-6 ]
[ 179083-28-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 511 - 514.

6
[ 13726-84-6 ]
(R)-4-[Isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-phenyl-carbamoyl}-4-(3-phenyl-ureido)-butyric acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 511 - 514.

7
[ 13726-84-6 ]
[ 179083-22-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 511 - 514.

8
[ 24424-99-5 ]
[ 13726-84-6 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 1253 - 1256.

9
[ 91103-36-5 ]
[ 13726-84-6 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 1253 - 1256.

10
[ 129016-13-3 ]
[ 13726-84-6 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 1253 - 1256.

11
[ 129016-14-4 ]
[ 13726-84-6 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 1253 - 1256.

12
2-deoxy-2<<(1,1-dimethylethoxy)carbonyl>amino>-D-glucopyranose [ No CAS ]
[ 13726-84-6 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 1253 - 1256.

13
[ 98102-32-0 ]
[ 13726-84-6 ]

References: [1]Justus Liebigs Annalen der Chemie,1964,vol. 673,p. 196 - 207.

14
[ 13726-84-6 ]
[ 130333-58-3 ]

Yield	Reaction Conditions	Operation in experiment
		18.1 18.2 l,l-Dimethylethyl (4i)-4-([(l,l-dimethylethyl)oxy]carbonyl}amino)-5-hydroxypentanoate: [00220] Triethylamine (11.49 mL, 82.4 mmol) and ethyl chloroformate (8.27 niL, 86.5 mmol) were added successively by syringe to 2V-t-BOC-D-glutamic acid 5-tert-bviotatyl ester (25 g, 82.4 mmol) in THF (588 mL) at <0 0C (ice-salt bath). After stirring in the cold bath for 40 min, solids were filtered and washed with THF (150 mL). The filtrate was transferred to a 250-mL addition funnel and added to a solution of sodium borohydride (8.42 g, 222.5 mmol) in H2O (114 mL) at 00C over 1 hour. The reaction mixture was maintained at 0 0C for 1.5 h and then stirred for 16 h (00C to room temperature). After the bulk of solvents were removed by rotary evaporation, the concentrate was quenched with ice water (50 mL) and 1 N HCl (50 mL). After extraction with EtOAc (4 x 100 mL), the extracts were washed with 100 mL: 0.5 M citric acid, saturated NaHCO3, H2O, and brine and concentrated in vacuo to give the title compound, which was used directly in the next step. ESMS [M+H]+ = 290.4, [2M+H]+ = 579.4. (Literature prep: J. Med. Chan, 1999, 42(1), 95-108 for other isomer).

References: [1]Patent: WO2007/56056,2007,A2 .Location in patent: Page/Page column 74.

15
C₃₀H₃₈FN₅O₇S [ No CAS ]
[ 13726-84-6 ]
C₄₄H₆₁FN₆O₁₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	GENERAL PROCEDURE FOR THE COUPLING OF AMINES WITH CARBOXYLIC ACIDS: The compound is dissolved in an appropriate amount of dichloromethane and the carboxylic acid (1.1 equiv.) added followed by PS-CDI (2 equiv.) and DIEA (10 equiv.). The reaction is shaken at room temperature until the starting material has been consumed. Once complete, the reaction is filtered and the filtrate concentrated in vacuo to obtain the crude product. In most cases, the crude product is pure enough for further transformations. If the crude product is not sufficiently pure, it can be purified using normal or reverse phase chromatography.

References: [1]Patent: US2009/93533,2009,A1 .Location in patent: Page/Page column 33; 34.

16
[ 865997-30-4 ]
[ 13726-84-6 ]
(4R)-4-amino-5-{2-[({1-butyl-4-[([4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazol-2-yl}carbonyl)amino]ethoxy}-5-oxopentanoic acid hydrochloride [ No CAS ]

References: [1]Patent: WO2005/92865,2005,A1 .Location in patent: Page/Page column 88.

17
[ 13726-84-6 ]
[ 85-61-0 ]
C₃₅H₅₉N₈O₂₁P₃S [ No CAS ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 13523 - 13530.

18
[ 919527-90-5 ]
[ 13726-84-6 ]
[ 76-05-1 ]
tert-butyl (4R)-4-[N-(6-aminohexanoylamino)carbamoyl]-4-[(tert-butoxy)carbonylamino]butanoate trifluoroacetic acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.6%		A solution of Boc-D-Glu(But)-OH (37.2 mg, 0.123 mmol) and HOAt (14.0 mg, 0.103 mmol) in dry DMF (1.00 mL) was successively treated with collidine (75.5 muL, 0.571 mmol) and DIC (16.0 muL, 0.102 mmol) then stirred 5 minutes at 22 C. The product of Example 3 A (30.0 mg, 62.3 mumol) was added in one portion and the resulting solution stirred 1.5 hours at 22 C. All volatiles were then removed in vacuo, and the resulting oil treated with a solution of tris(2-aminoethyl)amine in DMF (1:4 v/v, 4.00 mL). The solution was stirred 0.5 hours, then concentrated in vacuo and the crude residue purified by HPLC on a Phenomenex Luna Cl 8 column (21.2 x 250 mm) using a 1.0%/min gradient of 15-45% acetonitrile containing 0.1% TFA at a flow rate of 20 mL/min. The main product peak eluting at 17 minutes was lyophilized to a white solid (24.3 mg, 44.6 mumol; 71.6%). 1H NMR (DMSO-J6, 600 MHz): delta 8.77 (IH, s), 8.68 (IH, s), 7.32 (3H, br s), 5.76 (IH, br s), 4.11 (IH, br s), EPO <DP n="73"/>2.96 (2H, t, J= 6.8 Hz), 2.22 (2H, t J= 6.8 Hz), 2.02-1.97 (IH, m), 1.85-1.80 (IH, m), 1.70 (2H, tt, J= 7.6, 7.5 Hz), 1.65 (2H, tt, J= 7:0, 6.9 Hz), 1.54 (2H, m), 1.44 (9H, s), 1.42 (9H, s). MS (ESI): 431.3 (100, M+H).

References: [1]Patent: WO2007/5491,2007,A1 .Location in patent: Page/Page column 71-72.

19
[ 13726-84-6 ]
[ 84605-18-5 ]
[ 1255152-14-7 ]
[ 1255151-93-9 ]
C₅₈H₉₆N₂O₁₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9%		Preparation of 17a, 17b, 17c: Boc-(L)-Glutamic acid (Bachem, Torrance, Calif.) (O-tBu) -OH (4.5 g, 14.82 mmols) was dissolved in 15 ml of DCM. To this was added 2.73 g (14.82 mmol) of pentafluorophenol. The reaction was cooled in an ice-bath followed by slow addition of 2.3 ml (14.82 mmols) of DIC. After complete addition the reaction mixture was stirred at room temperature for 30 minutes at which time the reaction mixture turned turbid (diisopropylcarbodimide-urea precipitation). To this mixture was then added 765 mg (1.56 mmols) of <strong>[84605-18-5]cycloastragenol</strong> 2 followed by 1.8 g (14.82 mmol) of DMAP and the reaction was stirred at room temperature for 24 hours. The reaction mixture was transferred into a sepratory funnel and washed with H2O (2×) 1% aq. HCl (2×), 0.1N aq. NaOH (2×), sat. NaHCO3 (3×), H2O (1×) and brine (1×), the organic layer was separated, dried over Na2SO4, filtered and the solvent was evaporated under vacuum. To the residue was then added 50 ml of diethylether and the urea was precipitated out. The filterate was evaporated and the residue was purified using flash chromatography with solvent gradient of 2%-5% MeOH in DCM to furnish 714 mg of (60%) of in-separable mixture of products 17a, 17b, 17c, and 140 mg, (9%) of the bis product (C3, C6) . The 1HNMR showed major amounts of 17a and 17b products with 2% of the regioisomer (17c).1HNMR of the mixture(17a, 17b and 17c): (CDCl3) delta ppm: 0.29 (1H, bs), 0.56 (1H, bs), 0.90-1.20 (m, 26H), 1.30-1.40 (s,m 25H), 1.48-1.65 (m, 3H), 1.82-1.92 (m, 2H), 2.16-2.22 (m, 2H), 2.42-2.50 (m, 2H), 3.20-3.40 (m, 1H), 3.55-3.61 (m, 1H), 3.82-3.96 (m, 1H), 4.42-4.50 (m, 1H), 4.62-4.71 (m, 1H), 4.79-4.81 (m, 1H), 4.95-5.01 (m, 1H), 5.13-5.21 (m, 1H), 5.38-5.41 (m, 1H) . MS (M+H) 776.

References: [1]Patent: US2010/292197,2010,A1 .Location in patent: Page/Page column 23-24.

20
[ 13726-84-6 ]
C₂₉H₅₁N₃O₁₀ [ No CAS ]