153645-26-2|(S)-tert-Butyl (1-hydroxy-3,3-dimethylbutan-2-yl)carbamate| Ambeed

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Quality Control of [ 153645-26-2 ] Purity: 95% SDS Specification

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Product Details of [ 153645-26-2 ]

CAS No. :	153645-26-2
Formula :	C₁₁H₂₃NO₃
M.W :	217.31
SMILES Code :	CC(C)(C)[C@@H](CO)NC(OC(C)(C)C)=O
MDL No. :	MFCD01861301
InChI Key :	AZHJHZWFJVBGIL-MRVPVSSYSA-N
Pubchem ID :	10376058

Safety of [ 153645-26-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P264-P270-P301+P312-P330

Computational Chemistry of [ 153645-26-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	0
Fraction Csp3	0.91
Num. rotatable bonds	6
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	60.41
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.	2.82
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	2.04
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.92
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.	1.55
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	1.14
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.89

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.08
Solubility	1.82 mg/ml ; 0.00839 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.	-2.9
Solubility	0.275 mg/ml ; 0.00127 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	-1.93
Solubility	2.57 mg/ml ; 0.0118 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	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	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.	-6.18 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)	2.84

Application In Synthesis of [ 153645-26-2 ]

* 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.

Downstream synthetic route of [ 153645-26-2 ]

[ 153645-26-2 ] Synthesis Path-Downstream 1~35

1
[ 20859-02-3 ]
[ 24424-99-5 ]
[ 153645-26-2 ]

References: [1]Tetrahedron Asymmetry,2000,vol. 11,p. 1907 - 1910.
[2]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 4486 - 4495.
[3]Journal of Medicinal Chemistry,1995,vol. 38,p. 3821 - 3828.

2
[ 1826-67-1 ]
[ 153645-26-2 ]
[ 170240-97-8 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3821 - 3828.

3
[ 124-63-0 ]
[ 153645-26-2 ]
[ 862120-57-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 3h;Inert atmosphere;	General procedure: Mesylchloride (180 mul, 2.32 mmol) was added dropwise to a solution of tert-butyl [(1S)-1-cyclohexyl-2-hydroxyethyl]carbamate (17a) (4.0 g, 16.46 mmol) and TEA (6.8 mL, 49.38 mmol) in DCM (30 mL) at -0 C. The solution was stirred at 0 C under an atmosphere of argon for 3 h. The reaction mixture was poured into ice/water and the separated aqueous layer was re-extracted with DCM (5 mL). The combined organic layers were washed with 0.5 N HCl, water, saturated aqueous NaHCO3 sol and brine, dried (MgSO4) and the solvent was removed in vacuo to afford (2S)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethyl methanesulfonate (18) as an orange oil (4.35 g) that was used in the next step without purification.

References: [1]Tetrahedron Letters,2010,vol. 51,p. 1276 - 1279.
[2]Tetrahedron Asymmetry,1996,vol. 7,p. 2145 - 2150.
[3]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 567 - 570.
[4]Angewandte Chemie - International Edition,2010,vol. 49,p. 4467 - 4470.
[5]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 7364 - 7380.
[6]Organic and Biomolecular Chemistry,2019,vol. 17,p. 6351 - 6354.

4
[ 176504-88-4 ]
[ 153645-26-2 ]

References: [1]Tetrahedron Asymmetry,1996,vol. 7,p. 2145 - 2150.

5
[ 98-59-9 ]
[ 153645-26-2 ]
[ 229485-69-2 ]

References: [1]European Journal of Organic Chemistry,1999,p. 1475 - 1479.
[2]European Journal of Organic Chemistry,2002,p. 2776 - 2784.
[3]Journal of Organic Chemistry,2000,vol. 65,p. 4227 - 4240.
[4]New Journal of Chemistry,2020,vol. 44,p. 1648 - 1655.

6
[ 136918-14-4 ]
[ 153645-26-2 ]
[ 290815-00-8 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 2.5h;	To a solution of phthalimide (1.01 g) in 50 mL of dry THF was added triphenylphosphine (3 eq) and alcohol 3b (1 eq). The mixture was cooled in an ice-water bath and diisopropyl azodicarboxylate (2.5 eq) was added dropwise. The resulting mixture was stirred at 0 C. for 10 min and warmed to room temp and stirred for approximately 2.5 h until no more starting material was detected by TLC (ethyl acetate/hexanes; 3:7). The mixture was concentrated under reduced pressure. The residue was resuspended in 80 mL of dichloromethane. The solids were filtered off. The filtrate was concentrated to half its volume and hexanes (30 mL) were added. The solids were filtered off. The filtrate was concentrated under reduced pressure and the residue was chromatographed on silica gel (gradient: ethyl acetate/hexanes; 1:9 to 4:6) to give the product 3c.

References: [1]Tetrahedron Asymmetry,2000,vol. 11,p. 1907 - 1910.
[2]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 4486 - 4495.
[3]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1113 - 1118.
[4]Patent: US2005/197301,2005,A1 .Location in patent: Page/Page column 123.
[5]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1105 - 1109.
[6]Journal of Medicinal Chemistry,2009,vol. 52,p. 1370 - 1379.
[7]Organic Letters,2015,vol. 17,p. 4870 - 4873.

7
[ 24424-99-5 ]
[ 112245-13-3 ]
[ 153645-26-2 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 1188 - 1197.
[2]Journal of Organic Chemistry,2000,vol. 65,p. 4227 - 4240.
[3]Journal of Organic Chemistry,2006,vol. 71,p. 8283 - 8286.
[4]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2132 - 2142.
[5]Journal of the American Chemical Society,2013,vol. 135,p. 15742 - 15745.
[6]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 111 - 119.
[7]Organic Letters,2015,vol. 17,p. 4870 - 4873.
[8]Organic and Biomolecular Chemistry,2019,vol. 17,p. 6351 - 6354.
[9]New Journal of Chemistry,2020,vol. 44,p. 1648 - 1655.

8
[ 335628-21-2 ]
[ 153645-26-2 ]

References: [1]Organic letters,2001,vol. 3,p. 897 - 899.

9
[ 153645-26-2 ]
[ 335627-99-1 ]

Yield	Reaction Conditions	Operation in experiment
10 g	With Dess-Martin periodane; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h;	To a solution of <strong>[153645-26-2](S)-tert-butyl (1-hydroxy-3,3-dimethylbutan-2-yl)carbamate</strong> (10 g, 46.0 mmol) in DCM (50 mL) was added Dess-Martin periodinane (39.0 g, 92 mmol) portion wise at 0 C. and the reaction mixture was stirred at rt for 2 h. The reaction mixture was quenched with 10% NaHCO3, diluted with DCM. The organic layer was separated and washed with 10% NaHCO3. Then the organic layer was filtered through diatomaceous earth (Celite), washed with DCM. The combined filtrate was dried over Na2SO4and concentrated. The crude was dissolved in diethyl ether and again filtered through diatomaceous earth (Celite), washed with diethyl ether. The combined filtrate was concentrated and dried to obtain aldehyde B-1f (10 g) as a white solid.1H NMR (CDCl3, delta=7.26 ppm, 400 MHz): delta 9.82 (s, 1H), 5.13 (br s, 1H), 4.17 (d, J=8.4, 1H), 1.44 (s, 9H), 1.04 (s, 9H).
10 g	With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 2h;	To a solution of (S)-tert-butyl (l-hydroxy-3,3-dimethylbutan-2-yl)carbamate (10 g, 46.0 mmol) in DCM (50 mL) was added Dess-Martin periodinane (39.0 g, 92 mmol) portion wise at 0 C and the reaction mixture was stirred at rt for 2 h. The reaction mixture was quenched with 10% aHC03, diluted with DCM. The organic layer was separated and washed with 10% NaHC03. Then the organic layer was filtered through diatomaceous earth (Celite ), washed with DCM. The combined filtrate was dried over a2S04and concentrated. The crude was dissolved in diethyl ether and again filtered through diatomaceous earth (Celite ), washed with diethyl ether. The combined filtrate was concentrated and dried to obtain aldehyde B-lf (10 g) as a white solid.XH NMR (CDC13, delta = 7.26 ppm, 400 MHz): delta 9.82 (s, 1 H), 5.13 (br s, 1 H), 4.17 (d, J = 8.4, 1 H), 1.44 (s, 9 H), 1.04 (s, 9 H).

References: [1]Bioorganic and medicinal chemistry letters,2004,vol. 14,p. 275 - 278.
[2]Journal of Organic Chemistry,2015,vol. 80,p. 11184 - 11188.
[3]Synlett,2005,p. 2110 - 2112.
[4]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 111 - 119.
[5]Journal of Organic Chemistry,2004,vol. 69,p. 4541 - 4544.
[6]Patent: US2015/23913,2015,A1 .Location in patent: Paragraph 1003-1004.
[7]Patent: WO2015/5901,2015,A1 .Location in patent: Page/Page column 372.
[8]Organic Letters,2016,vol. 18,p. 4518 - 4521.

10
C₁₅H₂₇NO₆ [ No CAS ]
[ 153645-26-2 ]

References: [1]Bioorganic and medicinal chemistry letters,2004,vol. 14,p. 275 - 278.

11
[ 81-08-3 ]
[ 153645-26-2 ]
(S)-2-amino-3,3-dimethylbutyl 2-sulfobenzoate [ No CAS ]