[ CAS No. 159610-93-2 ] {[proInfo.proName]}

Name: 159610-93-2|(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-methoxypropanoic acid|98%
Brand: Ambeed
SKU: A394173
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Quality Control of [ 159610-93-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 159610-93-2 ]

SDS Specification

Alternatived Products of [ 159610-93-2 ]

Product Details of [ 159610-93-2 ]

CAS No. :	159610-93-2	MDL No. :	MFCD02682604
Formula :	C₁₉H₁₉NO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YFWAFELGMGZCHL-KRWDZBQOSA-N
M.W :	341.36	Pubchem ID :	46737425
Synonyms :

Calculated chemistry of [ 159610-93-2 ]

Physicochemical Properties

Num. heavy atoms :	25
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.26
Num. rotatable bonds :	8
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	91.06
TPSA :	84.86 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 :	No
Log Kp (skin permeation) :	-6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.41
Log Po/w (XLOGP3) :	2.54
Log Po/w (WLOGP) :	2.62
Log Po/w (MLOGP) :	1.74
Log Po/w (SILICOS-IT) :	2.47
Consensus Log Po/w :	2.36

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.38
Solubility :	0.141 mg/ml ; 0.000413 mol/l
Class :	Soluble
Log S (Ali) :	-3.97
Solubility :	0.0367 mg/ml ; 0.000107 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.02
Solubility :	0.00324 mg/ml ; 0.00000951 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.9

Safety of [ 159610-93-2 ]

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

Application In Synthesis of [ 159610-93-2 ]

* 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 [ 159610-93-2 ]
Downstream synthetic route of [ 159610-93-2 ]

[ 159610-93-2 ] Synthesis Path-Upstream 1~1

1
[ 28920-43-6 ]
[ 159610-93-2 ]

Reference： [1] Patent: US2007/105786, 2007, A1, . Location in patent: Page/Page column 33; 34

[ 159610-93-2 ] Synthesis Path-Downstream 1~88

1
[ 28920-43-6 ]
[ 159610-93-2 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of L-serine (methyl ether) hydrochloride (069) (1.0 g, 6.4 mmol) in water/dioxane (1:1, 80 ml) was added sodium hydroxide (768 mg, 19.2 mmol). After the mixture was stirred at room temperature for 30 minutes, it was cooled to 0 ° C., and a solution of 9-fluorenylmethyl chloroformate (1.65 g, 6.4 mmol) in dioxane (16 mL) was added dropwisely. The reaction mixture was allowed to stir at room temperature for another 4 hours. The solvents were then removed, the residue was diluted with water and the pH was adjusted to 1 with 1N HCl, and the aqueous layer was extracted with ethyl acetate (4.x.100 mL). The organic layers were concentrated under reduced pressure and placed under high vacuum to provide (070) (1.8 g) as confirmed by LC/MS (LCRS (MH) m/z: 342.13) which was used without further purification.

Reference： [1]Patent: US2007/105786,2007,A1 .Location in patent: Page/Page column 33; 34

2
[ 159610-93-2 ]
HMPB-BHA resin [ No CAS ]
C₄₄H₄₃N₂O₈Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1-methyl-1H-imidazole; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole; In dichloromethane;	The resin HMPB-BHA (500 mg, 0.32 mmol ) was washed with dichloromethane. In a dry flask, <strong>[159610-93-2]Fmoc-Ser(Me)-OH</strong> (070) (546 mg, 1.6 mmol) was dissolved in dichloromethane and to the solution was added 1-methylimidazole (95 muL, 1.2 mmol) followed by MSNT (474 mg, 1.6 mmol). Once the resulting mixture had become homogenous (10 minutes) it was added to the HMPB-BHA resin as a suspension in dichloromethane (5 mL). The resulting reaction mixture was allowed to shake overnight. The resin was then filtered off and washed with DMF (3.x.20 mL), MeOH (3.x.20 mL), DCM (3.x.20 mL), and allowed to air dry to yield (071).

Reference： [1]Patent: US2007/105786,2007,A1 .Location in patent: Page/Page column 33; 34

3
fmoc-Leu-Alko Resin [ No CAS ]
[ 159610-93-2 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 71989-31-6 ]
[ 71989-38-3 ]
[ 64-19-7 ]
Ac-PLG-S(OMe)YL [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 853 - 856

4
[ 159610-93-2 ]
H-cysteine(trityl)-2-chlorotrityl resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 67436-13-9 ]
[ 119831-72-0 ]
FFC(Acm)PFGC(t-Bu)ALVDCGPNRPC(t-Bu)RDTGF-(L-O-methylhomoserinyl)-SC(Acm)DC [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 1476 - 1481

5
[ 50-00-0 ]
[ 159610-93-2 ]
C₂₀H₁₉NO₅ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 7043 - 7052

6
[ 159610-93-2 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 71989-28-1 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Fmoc-Arg(pg)-OH [ No CAS ]
H-His-Ser(Me)-Gln-Gly-Thr-Phe-Thr-Ser-Asp-Leu-Ser-Lys-Gln-Met-Asp-Ser-Arg-Arg-Ala-Gln-Asp-Phe-Ile-Glu-Trp-Leu-Lys-Asn-Gly-Gly-Pro-Ser-Ser-Gly-Ala-Pro-Pro-Pro-Ser-NH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: The solid phase peptide syntheses were performed on a Prelude Peptide Synthesizer (Protein Technologies Inc) using standard Fmoc chemistry and HBTU/DIPEA activation. DMF was used as the solvent. Deprotection: 20percent piperidine/DMF for 2×2.5 min. Washes: 7×DMF. Coupling 2:5:10 200 mM AA/500 mM HBTU/2M DIPEA in DMF 2× for 20 min. Washes: 5×DMF. In cases where a Lys-side-chain was modified, Fmoc-L-Lys(ivDde)-OH was used in the corresponding position. After completion of the synthesis, the ivDde group was removed according to a literature procedure (S. R. Chhabra et al., Tetrahedron Lett. 39, (1998), 1603). The following acylations were carried out by treating the resin with the N-hydroxy succinimide esters of the desired acid or using coupling reagents like HBTU/DIPEA or HOBt/DIC. (0270) All the peptides that had been synthesized were cleaved from the resin with King's cleavage cocktail consisting of 82.5percent TFA, 5percent phenol, 5percent water, 5percent thioanisole, 2.5percent EDT. The crude peptides were then precipitated in diethyl or diisopropyl ether, centrifuged, and lyophilized. Peptides were analyzed by analytical HPLC and checked by ESI mass spectrometry. Crude peptides were purified by a conventional preparative HPLC purification procedure. Example 1 The solid phase synthesis was carried out on Rink-resin with a loading of 0.38 mmol/g, 75-150 mum from the company Agilent Technologies. The Fmoc-synthesis strategy was applied with HBTU/DIPEA-activation. The peptide was cleaved from the resin with King's cocktail (D. S. King, C. G. Fields, G. B. Fields, Int. J. Peptide Protein Res. 36, 1990, 255-266). The crude product was purified via preparative HPLC on a Waters column (XBridge, BEH130, Prep C18, 5 muM) using an acetonitrile/water gradient (both buffers with 0.1percent TFA). (0296) Finally, the molecular mass of the purified peptide was confirmed by LC-MS. M.W. (calculated)=4188.5 g/mol; M.W. (found)=4188.6 g/mol.

Reference： [1]Patent: US9181305,2015,B2 .Location in patent: Page/Page column 58; 59; 62; 63; 69; 70

7
[ 159610-93-2 ]
[ 35661-39-3 ]
Fmoc-L-Lys(iPr,Boc)-OH [ No CAS ]
[ 35661-40-6 ]
[ 71989-38-3 ]
HO-Phe-Tyr(tBu)-Ser(Me)-Ala-Lys(iPr,Boc)-NH2 [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 506 - 509

8
[ 159610-93-2 ]
[ 35661-39-3 ]
Fmoc-Lys(Cbz)-OH [ No CAS ]
[ 112883-29-1 ]
[ 35661-40-6 ]
HO-Ala-Lys(Cbz)-Phe-Tyr-Ser(Me)-NH2 [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 506 - 509

9
(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(dimethylamino)hexanoic acid [ No CAS ]
[ 159610-93-2 ]
[ 35661-40-6 ]
[ 132388-59-1 ]
[ 77128-72-4 ]
HO-Phe-Tyr(Me)-Ser(Me)-Asn(Trt)-Lys(Me)2-NH2 [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 506 - 509

10
(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(dimethylamino)hexanoic acid [ No CAS ]
[ 159610-93-2 ]
[ 132388-59-1 ]
[ 77128-72-4 ]
HO-Ser(Me)-Asn(Trt)-Lys(Me)2-Asn(Trt)-Tyr(Me)-NH2 [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 506 - 509

11
[ 3235-69-6 ]
[ 159610-93-2 ]
C₂₆H₁₉N₂O₅Pol [ No CAS ]
[ 132684-59-4 ]
[ 95753-56-3 ]
Mor-Hfe-Ser(Me)-Phe(4-NH₂)-ACC [ No CAS ]