[ CAS No. 185836-75-3 ] {[proInfo.proName]}

Name: 185836-75-3|(R)-4-(tert-Butoxy)-2-methyl-4-oxobutanoic acid|98%
Brand: Ambeed
SKU: A213232
Price: 24.0 USD
Availability: InStock
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Quality Control of [ 185836-75-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 185836-75-3 ]

Product Details of [ 185836-75-3 ]

CAS No. :	185836-75-3	MDL No. :	MFCD01862170
Formula :	C₉H₁₆O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RSLMNCHJSYDERN-ZCFIWIBFSA-N
M.W :	188.22	Pubchem ID :	10845285
Synonyms :

Calculated chemistry of [ 185836-75-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.78
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.47
TPSA :	63.6 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.98
Log Po/w (XLOGP3) :	1.1
Log Po/w (WLOGP) :	1.44
Log Po/w (MLOGP) :	1.25
Log Po/w (SILICOS-IT) :	0.94
Consensus Log Po/w :	1.34

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.37
Solubility :	8.03 mg/ml ; 0.0427 mol/l
Class :	Very soluble
Log S (Ali) :	-2.03
Solubility :	1.76 mg/ml ; 0.00937 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.0
Solubility :	19.0 mg/ml ; 0.101 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.51

Safety of [ 185836-75-3 ]

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 [ 185836-75-3 ]

* 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.

Upstream synthesis route of [ 185836-75-3 ]
Downstream synthetic route of [ 185836-75-3 ]

[ 185836-75-3 ] Synthesis Path-Upstream 1~13

1
[ 82701-21-1 ]
[ 182007-75-6 ]
[ 185836-75-3 ]

Reference： [1] Tetrahedron Asymmetry, 1999, vol. 10, # 17, p. 3285 - 3295

2
[ 202874-73-5 ]
[ 185836-75-3 ]

Reference： [1] Journal of Organic Chemistry, 1999, vol. 64, # 17, p. 6411 - 6417
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 865 - 880

3
[ 23268-03-3 ]
[ 185836-75-3 ]

Reference： [1] Patent: US6355830, 2002, B1,
[2] Patent: US6355830, 2002, B1,
[3] Patent: US6355830, 2002, B1,

4
[ 908290-81-3 ]
[ 908290-56-2 ]
[ 185836-75-3 ]

Reference： [1] Organic and Biomolecular Chemistry, 2006, vol. 4, # 14, p. 2753 - 2768

5
[ 865-47-4 ]
[ 23268-03-3 ]
[ 185836-75-3 ]

Reference： [1] Patent: US6355830, 2002, B1,

6
[ 77-92-9 ]
[ 185836-75-3 ]

Reference： [1] Patent: US5753659, 1998, A,

7
[ 195829-02-8 ]
[ 185836-75-3 ]

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 17, p. 5830 - 5837

8
[ 170704-11-7 ]
[ 185836-75-3 ]

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 17, p. 5830 - 5837

9
[ 5292-43-3 ]
[ 185836-75-3 ]

Reference： [1] Organic and Biomolecular Chemistry, 2006, vol. 4, # 14, p. 2753 - 2768
[2] Journal of Organic Chemistry, 1999, vol. 64, # 17, p. 6411 - 6417
[3] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 865 - 880

10
[ 195828-95-6 ]
[ 185836-75-3 ]

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 17, p. 5830 - 5837

11
[ 195828-92-3 ]
[ 185836-75-3 ]

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 17, p. 5830 - 5837

12
[ 144843-09-4 ]
[ 185836-75-3 ]

Reference： [1] Tetrahedron Asymmetry, 1999, vol. 10, # 17, p. 3285 - 3295

13
[ 82701-21-1 ]
[ 182007-75-6 ]
[ 185836-75-3 ]

Reference： [1] Tetrahedron Asymmetry, 1999, vol. 10, # 17, p. 3285 - 3295

[ 185836-75-3 ] Synthesis Path-Downstream 1~75

1
[ 195829-02-8 ]
[ 185836-75-3 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5830 - 5837

2
[ 185836-75-3 ]
[ 100-51-6 ]
tert-butyl (3R)-3-[(benzyloxy)carbonyl]amino}butanoate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 6411 - 6417
[2]Journal of Organic Chemistry,1997,vol. 62,p. 5830 - 5837

3
[ 119072-55-8 ]
[ 630-19-3 ]
[ 185836-75-3 ]
(R)-N-(1-tert-Butylcarbamoyl-2,2-dimethyl-propyl)-3-methyl-succinamic acid tert-butyl ester [ No CAS ]

Reference： [1]Synlett,1998,p. 637 - 639

4
[ 185836-75-3 ]
[ 185836-76-4 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol;	Borane-dimethyl sulphide complex (10M, 10.3 ml) was added during 15 minutes to a stirred mixture of <strong>[185836-75-3]1-tert-butyl (3R)-3-methylsuccinate</strong> (12.9 g) and THF (200 ml) which had been cooled to -10 C. and placed under an atmosphere of argon. The mixture was stirred at -10 C. for 30 minutes. The mixture was allowed to warm to room temperature and was stirred for 1 hour. The mixture was recooled to 5 C. and methanol (50 ml) was added portionwise. The mixture was allowed to warm to room temperature and was stirred for 30 minutes. The mixture was evaporated and the residue was partitioned between dichloromethane (100 ml) and water (100 ml). The organic phase was filtered through phase separating paper and evaporated to give tert-butyl (3R)-4-hydroxy-3-methylbutyrate as an oil (11 g); NMR(CDCl3) delta 3.55(2H,m), 2.1-2.4(3H,m), 1.46(9H,s), 0.98(3H,d).
	In tetrahydrofuran; methanol;	Borane-dimethyl sulphide complex (10M, 10.3 ml) was added during 15 minutes to a stirred mixture of <strong>[185836-75-3]1-tert-butyl (3R)-3-methylsuccinate</strong> (12.9 g) and THF (200 ml) which had been cooled to -10 C. and placed under an atmosphere of argon. The mixture was stirred at -10 C. for 30 minutes. The mixture was allowed to warm to room temperature and was stirred for 1 hour. The mixture was recooled to 5 C. and methanol (50 ml) was added portionwise. The mixture was allowed to warm to room temperature and was stirred for 30 minutes. The mixture was evaporated and the residue was partitioned between dichloromethane (100 ml) and water (100 ml). The organic phase was filtered through phase separating paper and evaporated to give tert-butyl (3R)-4-hydroxy-3-methylbutyrate as an oil (11 g); NMR(CDCl3) delta 3.55(2H,m), 2.1-2.4(3H,m), 1.46(9H,s), 0.98(3H,d).

Reference： [1]European Journal of Organic Chemistry,1999,p. 2167 - 2173
[2]Bioscience, Biotechnology and Biochemistry,2002,vol. 66,p. 1389 - 1392
[3]Heterocycles,2005,vol. 66,p. 111 - 117
[4]Patent: US5652242,1997,A
[5]Patent: US5753659,1998,A
[6]Organic Letters,2008,vol. 10,p. 1675 - 1678

5
[ 202874-73-5 ]
[ 185836-75-3 ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 6411 - 6417
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 865 - 880

6
[ 82701-21-1 ]
[ 182007-75-6 ]
[ 185836-75-3 ]

Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 3285 - 3295

7
[ 908290-81-3 ]
[ 908290-56-2 ]
[ 185836-75-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2753 - 2768

8
[ 5292-43-3 ]
[ 185836-75-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2753 - 2768
[2]Journal of Organic Chemistry,1999,vol. 64,p. 6411 - 6417
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 865 - 880

9
[ 185836-75-3 ]
[ 881018-08-2 ]