160885-98-3|Fmoc-Valinol| Ambeed

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Quality Control of [ 160885-98-3 ] Purity: 96% SDS Specification

COA

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NMR

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CNMR

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Product Details of [ 160885-98-3 ]

CAS No. :	160885-98-3
Formula :	C₂₀H₂₃NO₃
M.W :	325.40
SMILES Code :	O=C(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)N[C@@H](C(C)C)CO
MDL No. :	MFCD00235961
InChI Key :	MYMGENAMKAPEMT-LJQANCHMSA-N
Pubchem ID :	688273

Safety of [ 160885-98-3 ]

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

Computational Chemistry of [ 160885-98-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	24
Num. arom. heavy atoms	12
Fraction Csp3	0.35
Num. rotatable bonds	7
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	94.18
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	58.56 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.25
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	3.77
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.54
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.	2.87
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	3.6
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.41

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.14
Solubility	0.0235 mg/ml ; 0.0000723 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.	-4.69
Solubility	0.0066 mg/ml ; 0.0000203 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	-5.78
Solubility	0.000541 mg/ml ; 0.00000166 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	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	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	Yes
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.	-5.61 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.	0.55

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<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)	3.85

Application In Synthesis of [ 160885-98-3 ]

* 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 [ 160885-98-3 ]

[ 160885-98-3 ] Synthesis Path-Downstream 1~35

1
[ 2026-48-4 ]
[ 28920-43-6 ]
[ 160885-98-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	In neat (no solvent); at 20℃; for 0.0333333h;Sonication; Irradiation; Green chemistry;	General procedure: Amine (1 mmol) and Fmoc-Cl (1.1 mmol) were placed in a glass tube under neat conditions and were sonicated for a suitable time (as indicated in Tables 1, 2 and 3). All reactions were performed in a water bath at room temperature. After completion of the reaction (as indicated by TLC), 5 cm3 of diethyl ether was added to the mixture. The N-Fmoc derivatives were crystallized and were obtained in good to excellent yields. Purification of the product was accomplished by recrystallization from diethyl ether.

References: [1]Journal of the Brazilian Chemical Society,2016,vol. 27,p. 546 - 550.
[2]Journal of Organic Chemistry,1995,vol. 60,p. 405 - 410.

2
[ 160885-98-3 ]
[ 156939-64-9 ]

References: [1]Journal of Medicinal Chemistry,2021,vol. 64,p. 4034 - 4058.
[2]Tetrahedron Asymmetry,1998,vol. 9,p. 1855 - 1858.
[3]Synlett,2005,p. 2110 - 2112.
[4]Synlett,2003,p. 2249 - 2251.

3
[ 84890-99-3 ]
[ 160885-98-3 ]

References: [1]Tetrahedron Asymmetry,1998,vol. 9,p. 1855 - 1858.
[2]Synthesis,2006,p. 455 - 460.
[3]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2397 - 2406.

4
[ 68858-20-8 ]
[ 160885-98-3 ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: To a solution of carboxylic acid (10 mmol) in THF (10 mL), DIPEA (11 mmol, 1.42 mL) and 50% T3P in EtOAc (20 mmol, 6.36 mL) were added at 0 C and the solution was stirred for about 10 min. Then aqueous solution of NaBH4 (10 mmol, 388 mg in 0.3 mL of H2O) was added to the reaction mixture at the same temperature and the reaction was allowed to stir till the completion of the reaction as indicated by TLC. After the completion of the reaction, the solvent was evaporated and the crude alcohol was extracted into EtOAc and the organic phase was washed with 5% citric acid (10 mL × 2), 5% Na2CO3 (10 mL × 2), water, and brine solution. The product was isolated after the evaporation of solvent under reduced pressure and dried over anhydrous Na2SO4.

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 8454 - 8462.
[2]Tetrahedron Letters,1999,vol. 40,p. 4395 - 4396.
[3]Tetrahedron Letters,2012,vol. 53,p. 5059 - 5063.
[4]RSC Advances,2014,vol. 4,p. 46947 - 46950.
[5]Organic and Biomolecular Chemistry,2011,vol. 9,p. 4182 - 4187.
[6]Chemistry - An Asian Journal,2020,vol. 15,p. 742 - 747.
[7]Tetrahedron Asymmetry,1998,vol. 9,p. 1855 - 1858.
[8]Journal of Organic Chemistry,2009,vol. 74,p. 5260 - 5266.
[9]Synthetic Communications,2009,vol. 39,p. 3555 - 3566.
[10]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2397 - 2406.
[11]Organic and Biomolecular Chemistry,2011,vol. 9,p. 4182 - 4187.
[12]ACS Combinatorial Science,2017,vol. 19,p. 131 - 136.
[13]Organic and Biomolecular Chemistry,2018,vol. 16,p. 4874 - 4880.
[14]Journal of Medicinal Chemistry,2021,vol. 64,p. 4034 - 4058.

5
[ 124-63-0 ]
[ 160885-98-3 ]
[ 311330-34-4 ]

References: [1]Synthesis,2000,p. 1579 - 1584.
[2]Tetrahedron Letters,2009,vol. 50,p. 3391 - 3393.
[3]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2397 - 2406.
[4]Tetrahedron Letters,2000,vol. 41,p. 7991 - 7995.
[5]Synthesis,2006,p. 455 - 460.
[6]ACS Combinatorial Science,2017,vol. 19,p. 131 - 136.

6
C₂₅H₂₉NO₆ [ No CAS ]
[ 160885-98-3 ]

References: [1]Synthesis,2000,p. 1579 - 1584.
[2]Tetrahedron Letters,2009,vol. 50,p. 3391 - 3393.
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2010,vol. 49,p. 1372 - 1378.

7
C₂₅H₂₉NO₆ [ No CAS ]
[ 160885-98-3 ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 7991 - 7995.

8
[ 98-00-0 ]
[ 135112-28-6 ]
[ 98-68-0 ]
[ 160885-98-3 ]
N-(2-furfuryl)-N-(4-methoxybenzenesulfonyl)-L-norvalinyl-L-valinol [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 5048 - 5056.

9
[ 636-72-6 ]
[ 135112-28-6 ]
[ 98-68-0 ]
[ 160885-98-3 ]
N-(2-thienylmethyl)-N-(4-methoxybenzenesulfonyl)-L-norvalinyl-L-valinol [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 5048 - 5056.

10
[ 624-95-3 ]
[ 135112-28-6 ]
[ 98-68-0 ]
[ 160885-98-3 ]
N-(3,3-dimethylbutyl)-N-(4-methoxybenzenesulfonyl)-L-norvalinyl-L-valinol [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 5048 - 5056.

11
[ 135112-28-6 ]
[ 98-68-0 ]
[ 160885-98-3 ]
[ 100-51-6 ]
N-benzyl-N-(4-methoxybenzenesulfonyl)-L-norvalinyl-L-valinol [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 5048 - 5056.

12
[ 160885-98-3 ]
[ 391624-28-5 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 8454 - 8462.
[2]Synlett,2006,p. 306 - 308.
[3]International Journal of Peptide Research and Therapeutics,2010,vol. 16,p. 267 - 275.
[4]Organic and Biomolecular Chemistry,2018,vol. 16,p. 4874 - 4880.

13
[ 29022-11-5 ]
[ 35661-40-6 ]
[ 160885-98-3 ]
Succinic acid mono-[(2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(9H-xanthen-9-ylsulfanyl)-tetrahydro-pyran-2-ylmethyl] ester [ No CAS ]
Fmoc-Ala-OH [ No CAS ]
(S)-2-Amino-N-({(S)-1-[(S)-2-methyl-1-((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanylmethyl)-propylcarbamoyl]-2-phenyl-ethylcarbamoyl}-methyl)-propionamide [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 9549 - 9552.

14
[ 82911-80-6 ]
[ 160885-98-3 ]

References: [1]European Journal of Organic Chemistry,2004,p. 463 - 467.

15
[ 135112-28-6 ]
[ 98-68-0 ]
[ 160885-98-3 ]
N-(4-methoxybenzenesulfonyl)-L-norvalinyl-L-valinol [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 5048 - 5056.

16
[ 160885-98-3 ]
N-Fmoc-Val-ψ[CH2-I] [ No CAS ]

References: [1]Synlett,2006,p. 306 - 308.
[2]Synlett,2010,p. 1037 - 1042.
[3]Journal of Organic Chemistry,2009,vol. 74,p. 5260 - 5266.
[4]Tetrahedron Letters,2009,vol. 50,p. 7062 - 7066.
[5]Synthesis,2011,p. 1447 - 1455.
[6]International Journal of Peptide Research and Therapeutics,2010,vol. 16,p. 267 - 275.
[7]Organic and Biomolecular Chemistry,2018,vol. 16,p. 4874 - 4880.

17
[ 329308-98-7 ]
[ 160885-98-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2006,vol. 45,p. 1880 - 1886.

18
[ 68858-20-8 ]
N-Fmoc-Glu(O-t-Butyl ester) [ No CAS ]
[ 160885-98-3 ]

References: [1]Synthesis,2006,p. 455 - 460.

19
[ 160885-98-3 ]
[ 311330-39-9 ]

References: [1]Synthesis,2006,p. 455 - 460.
[2]Tetrahedron Letters,2000,vol. 41,p. 7991 - 7995.
[3]Synthesis,2000,p. 1579 - 1584.
[4]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2397 - 2406.

20
[ 160885-98-3 ]
[2-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyl]-carbamic acid 4-nitro-phenyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 8454 - 8462.

21
[ 160885-98-3 ]
(9H-fluoren-9-yl)methyl (S)-1-amino-3-methylbutan-2-ylcarbamate hydrochloride [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 8454 - 8462.

22
[ 68858-20-8 ]
N_α-Fmoc-PN_α-Fmoc-S(t-Bu) [ No CAS ]
[ 160885-98-3 ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 7991 - 7995.
[2]Synthesis,2000,p. 1579 - 1584.

23
[ 75-44-5 ]
[ 160885-98-3 ]
[ 1037509-30-0 ]

References: [1]Synthetic Communications,2009,vol. 39,p. 3555 - 3566.

24
[ 119206-33-6 ]
[ 160885-98-3 ]

References: [1]Synlett,2010,p. 1037 - 1042.

25
[ 160885-98-3 ]
[ 1169199-25-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2397 - 2406.

26
[ 160885-98-3 ]
[ 311330-41-3 ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2397 - 2406.

27
[ 160885-98-3 ]
2-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-3-methyl-butane-1-sulfonic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2397 - 2406.

28
[ 160885-98-3 ]
[ 1327157-56-1 ]