852288-18-7|Fmoc-Dopa(acetonide)-OH| Ambeed

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Quality Control of [ 852288-18-7 ] Purity: 97% SDS Specification

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Product Details of [ 852288-18-7 ]

CAS No. :	852288-18-7
Formula :	C₂₇H₂₅NO₆
M.W :	459.49
SMILES Code :	O=C(O)[C@@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)CC4=CC=C(OC(C)(C)O5)C5=C4
MDL No. :	MFCD08064332
InChI Key :	SHZLOTJPHMTVDI-QFIPXVFZSA-N
Pubchem ID :	25058854

Safety of [ 852288-18-7 ]

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

Computational Chemistry of [ 852288-18-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	34
Num. arom. heavy atoms	18
Fraction Csp3	0.26
Num. rotatable bonds	8
Num. H-bond acceptors	6.0
Num. H-bond donors	2.0
Molar Refractivity	125.37
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	94.09 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.16
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	5.07
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.73
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.	3.37
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	4.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	4.17

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-5.75
Solubility	0.000823 mg/ml ; 0.00000179 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.	-6.79
Solubility	0.0000748 mg/ml ; 0.000000163 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly 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	-7.83
Solubility	0.00000684 mg/ml ; 0.0000000149 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly 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	Yes
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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.5 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	1.0
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)	4.44

Application In Synthesis of [ 852288-18-7 ]

* 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 [ 852288-18-7 ]

[ 852288-18-7 ] Synthesis Path-Downstream 1~35

1
Fmoc-Glu(Biotinyl-PEG)-OH [ No CAS ]
[ 852288-18-7 ]
[ 84624-27-1 ]
[ 79-08-3 ]
6-(9H-purin-6-ylamino)hexanoic acid [ No CAS ]
1,4-diaminobutane [ No CAS ]
C₁₀₃H₁₆₁N₂₅O₁₉S [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 12936 - 12937.

2
Fmoc-Glu(Biotinyl-PEG)-OH [ No CAS ]
[ 852288-18-7 ]
[ 84624-27-1 ]
[ 79-08-3 ]
isobutylamine [ No CAS ]
1,4-diaminobutane [ No CAS ]
C₆₈H₁₂₁N₁₇O₁₇S [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 12936 - 12937.

3
[ 852288-18-7 ]
[ 59-92-7 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 5519 - 5521.

4
[ 852288-18-7 ]
[ 29022-11-5 ]
[ 71989-26-9 ]
[ 1064196-12-8 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 5519 - 5521.

5
H-DOPA(acetonide)-OH [ No CAS ]
[ 82911-69-1 ]
[ 852288-18-7 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of Fmoc-DOPA(acetonide)-OH (7)The oil residue of H-DOPA(acetonide)-OMe (0.50 g, 2 mmol) was dissolved in 20 mL THF and cooled in an ice bath. Lithium hydroxide (0.96 g, 4 mmol) in cold water (7 mL) was added. The mixture was stirred at 0 C. for 2.5 h, treated with 1N HCl to a pH of 7-8, followed by addition of Na2CO3 (0.42 g, 4 mmol). Fmoc-OSu (0.68 g, 2 mmol) was added and the mixture was stirred at 0 C. for another 2 h. The mixture was then acidified with 1N HCl to a pH of 2-3. After THF was reduced by rotary evaporation, the mixture was extracted with EtOAc. The organic phase was washed with water, dried over MgSO4, concentrated to minimum amount. To the residue was added hexane, and the white precipitate was collected and purified by silica-gel flash chromatography (washed with DCM, and then eluted with DCM/EtOAc/MeOH (67:30:3), yield, 0.66 g (74%).Spectral Data. 1H NMR (500 MHz, CDCl3): delta 11.15 (br, 1H), 7.81-7.28 (m, 8H), 6.71-6.54 (m, 3H), 5.41 (d, 1H), 4.72 (m, 1H), 4.52-4.24 (m, 3H), 3.18-3.06 (m, 2H), 1.67 (s, 6H). 13C NMR (125 MHz, CDCl3): delta 176.5, 156.1, 147.8, 146.8, 143.92, 143.81, 141.4 (2C), 128.6, 127.9 (2C), 127.3 (2C), 125.28, 125.22, 122.1, 119.9 (2C), 118.2, 109.6, 108.4, 67.3, 54.9, 47.2, 37.6, 26.0 (2C). 13C NMR (125 MHz, CDCl3) DEPT: CH3, 26.0; CH2, 67.3, 37.6; CH, 127.9, 127.3, 125.28, 125.22, 122.1, 119.9, 109.6, 108.4, 54.9, 47.2. Ferric Chloride Test: negative at room temperature, positive at 105 C. ESI-MS: MH+, Calcd. 460.18. Found 459.85; M2Na+, Calcd. 941.33, Found 940.77. M3Na+, Calcd. 1400.49, Found 1400.49; M4Na+, Calcd. 1860.67, Found 1859.36. HRMS (ESI): C27H25NO6, MH+, Calcd. 460.17546, Found 460.17516 (FIG. 31).

References: [1]Tetrahedron Letters,2008,vol. 49,p. 5519 - 5521.
[2]Patent: US8227628,2012,B2 .Location in patent: Page/Page column 18-19; 20.

Yield	Reaction Conditions	Operation in experiment
		The mixture solution was neutralized with 1 N HCl to pH 7-8, followed by addition of sodium carbonate (2 equiv) and Fmoc-OSu (1 equiv) to provide Fmoc-DOPA(acetonide)-OH (7), which was further purified by silica-gel flash chromatography (DCM/EtOAc/MeOH) (two steps, 74%).24
0.66 g (74%)		Synthesis of Fmoc-DOPA(acetonide)-OH (7) The oil residue of H-DOPA(acetonide)-OMe (0.50 g, 2 mmol) was dissolved in 20 mL THF and cooled in an ice bath. Lithium hydroxide (0.96 g, 4 mmol) in cold water (7 mL) was added. The mixture was stirred at 0 C. for 2.5 h, treated with 1N HCl to a pH of 7-8, followed by addition of Na2CO3 (0.42 g, 4 mmol). Fmoc-OSu (0.68 g, 2 mmol) was added and the mixture was stirred at 0 C. for another 2 h. The mixture was then acidified with 1N HCl to a pH of 2-3. After THF was reduced by rotary evaporation, the mixture was extracted with EtOAc. The organic phase was washed with water, dried over MgSO4, concentrated to minimum amount. To the residue was added hexane, and the white precipitate was collected and purified by silica-gel flash chromatography (washed with DCM, and then eluted with DCM/EtOAc/MeOH (67:30:3), yield, 0.66 g (74%). Spectral Data. 1H NMR (500 MHz, CDCl3): delta 11.15 (br, 1H), 7.81-7.28 (m, 8H), 6.71-6.54 (m, 3H), 5.41 (d, 1H), 4.72 (m, 1H), 4.52-4.24 (m, 3H), 3.18-3.06 (m, 2H), 1.67 (s, 6H). 13C NMR (125 MHz, CDCl3): delta 176.5, 156.1, 147.8, 146.8, 143.92, 143.81, 141.4 (2C), 128.6, 127.9 (2C), 127.3 (2C), 125.28, 125.22, 122.1, 119.9 (2C), 118.2, 109.6, 108.4, 67.3, 54.9, 47.2, 37.6, 26.0 (2C). 13C NMR (125 MHz, CDCl3) DEPT: CH3, 26.0; CH2, 67.3, 37.6; CH, 127.9, 127.3, 125.28, 125.22, 122.1, 119.9, 109.6, 108.4, 54.9, 47.2. Ferric Chloride Test: negative at room temperature, positive at 105 C. ESI-MS: MH+, Calcd. 460.18. Found 459.85; M2Na+, Calcd. 941.33, Found 940.77. M3Na+, Calcd. 1400.49, Found 1400.49; M4Na+, Calcd. 1860.67, Found 1859.36. HRMS (ESI): C27H25NO6, MH+, Calcd. 460.17546, Found 460.17516 (

7
[ 852288-18-7 ]
[ 108-24-7 ]
[ 1266235-83-9 ]

References: [1]Chemistry of Materials,2011,vol. 23,p. 1130 - 1135.

8
[ 59-92-7 ]
[ 852288-18-7 ]

References: [1]Patent: US8227628,2012,B2 .
[2]Patent: US8227628,2012,B2 .

9
[ 297144-73-1 ]
[ 852288-18-7 ]