56762-93-7|(S)-Methyl 2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanoate| Ambeed

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Quality Control of [ 56762-93-7 ] Purity: 98% SDS Specification

COA

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NMR

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Product Details of [ 56762-93-7 ]

CAS No. :	56762-93-7
Formula :	C₁₄H₁₉NO₄S
M.W :	297.37
SMILES Code :	O=C(OC)[C@@H](NC(OCC1=CC=CC=C1)=O)CCSC
MDL No. :	MFCD00145551
InChI Key :	YGDBSBBHEWHVAJ-LBPRGKRZSA-N
Pubchem ID :	11141035

Safety of [ 56762-93-7 ]

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

Computational Chemistry of [ 56762-93-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	6
Fraction Csp3	0.43
Num. rotatable bonds	10
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	78.41
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	89.93 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.53
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	2.4
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.06
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.	1.96
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	2.23
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.24

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.76
Solubility	0.52 mg/ml ; 0.00175 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.	-3.93
Solubility	0.0349 mg/ml ; 0.000117 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	-3.97
Solubility	0.0322 mg/ml ; 0.000108 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	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	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	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	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.	-6.41 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	1.0 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)	3.31

Application In Synthesis of [ 56762-93-7 ]

* 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 [ 56762-93-7 ]

[ 56762-93-7 ] Synthesis Path-Downstream 1~35

1
[ 186581-53-3 ]
[ 1152-62-1 ]
[ 56762-93-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 1149 - 1158.
[2]Helvetica Chimica Acta,1951,vol. 34,p. 2085,2093.
[3]Chemical and Pharmaceutical Bulletin,1975,vol. 23,p. 3081 - 3087.

2
[ 56762-93-7 ]
[ 15998-52-4 ]

References: [1]Journal of Biological Chemistry,1949,vol. 180,p. 155,157.

3
[ 56762-93-7 ]
[ 3561-51-1 ]

References: [1]Helvetica Chimica Acta,1951,vol. 34,p. 2085,2093.

4
[ 867-13-0 ]
[ 56762-93-7 ]
[ 151929-39-4 ]

References: [1]Tetrahedron,1994,vol. 50,p. 5569 - 5578.

5
[ 56762-93-7 ]
[ 1152-62-1 ]

References: [1]Collection of Czechoslovak Chemical Communications,1989,vol. 54,p. 2027 - 2041.

6
[ 56762-93-7 ]
[ 75266-39-6 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water;	(S)-2-Benzyloxycarbonylamino-4-methanesulfinyl-butyric acid methyl ester (60) Sulfide 59 (5.40 g, 18.2 mmol) was dissolved in methanol (60 mL). This was cooled in ice and a solution of sodium metaperiodate (4.08 g, 1.05 equiv) in water (25 mL) was added dropwise over 10 mins. This was stirred in ice for 1 h and then at rt for a further 2 h. The resultant white precipitate was removed by filtration under vacuum, the residue washed with methanol and the filtrate concentrated in vacuo. The resultant colourless oil was partitioned between DCM and water. The aqueous phase was extracted twice more with DCM, methanol added to the combined organic extracts to obtain an homogenous solution and this was dried (MgSO4), filtered and concentrated in vacuo to afford a yellow oil, 5.69 g, 100%. This was obtained as a 1:1 mixture of diastereoisomers. 1H-NMR (500 MHz in CDCl3) 7.30-7.35 (5H, m, Ar-H), 6.00-6.08 (1H, m, NH), 5.10 (2H, s, CH2Ph), 4.44-4.50 (1H, m, CHCO2CH3), 3.75 (3H, s, CHCO2CH3), 2.67-2.77 (2H, m, CHCH2CH2S), 2.53-2.54 (3H, m, SCH3), 2.32-2.40 (1H, m, CHCH2CH2S), 2.09-2.19 (1H, m, CHCH2CH2S). 13C-NMR (75 MHz in CDCl3) 172.6, 156.0, 136.2, 128.6, 128.4, 128.3, 128.1, 128.0, 69.9, 53.5, 53.0, 52.4, 31.6, 29.8, 15.3. LRMS (ES) 314.1 (MH+). C14H19NO5S requires 314.1.
	With sodium periodate; In methanol; water; at 20℃; for 3.0h;Cooling with ice;	Sulfide 59 (5.40 g, 18.2 mmol) was dissolved in methanol (60 mL). This was cooled in ice and a solution of sodium metaperiodate (4.08 g, 1.05 equiv) in water (25 mL) was added dropwise over 10 mins. This was stirred in ice for 1 h and then at rt for a further 2 h. The resultant white precipitate was removed by filtration under vacuum, the residue washed with methanol and the filtrate concentrated in vacuo. The resultant colourless oil was partitioned between DCM and water. The aqueous phase was extracted twice more with DCM, methanol added to the combined organic extracts to obtain an homogenous solution and this was dried (MgSO4), filtered and concentrated in vacuo to afford a yellow oil, 5.69 g, 100%. This was obtained as a 1:1 mixture of diastereoisomers. 1H-NMR (500 MHz in CDCl3) 7.30-7.35 (5H, m, Ar-H), 6.00-6.08 (1H, m, NH), 5.10 (2H, s, CH2Ph), 4.44-4.50 (1H, m, CHCO2CH3), 3.75 (3H, s, CHCO2CH3), 2.67-2.77 (2H, m, CHCH2CH2S), 2.53-2.54 (3H, m, SCH3), 2.32-2.40 (1H, m, CHCH2CH2S), 2.09-2.19 (1H, m, CHCH2CH2S). 13C-NMR (75 MHz in CDCl3) 172.6, 156.0, 136.2, 128.6, 128.4, 128.3, 128.1, 128.0, 69.9, 53.5, 53.0, 52.4, 31.6, 29.8, 15.3. LRMS (ES) 314.1 (MH+). C14H19NO5S requires 314.1.

References: [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 1149 - 1158.
[2]Amino Acids,2010,vol. 39,p. 443 - 448.
[3]Organic Syntheses,1992,vol. 70,p. 29 - 29.
[4]Tetrahedron Letters,2010,vol. 51,p. 3226 - 3228.
[5]Synthetic Communications,1989,vol. 19,p. 3457 - 3468.
[6]Journal of Organic Chemistry,1980,vol. 45,p. 4817 - 4820.
[7]Synthetic Communications,1987,vol. 17,p. 515 - 520.
[8]Chemistry - A European Journal,2004,vol. 10,p. 544 - 553.
[9]Journal of Organic Chemistry,1988,vol. 53,p. 561 - 569.
[10]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 893 - 901.
[11]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 325 - 328.
[12]European Journal of Organic Chemistry,2008,p. 3107 - 3112.
[13]Patent: US2011/21434,2011,A1 .
[14]Patent: US9434762,2016,B2 .Location in patent: Page/Page column 91; 92.

7
[ 56762-93-7 ]
[ 115527-65-6 ]

References: [1]Tetrahedron,1987,vol. 43,p. 5363 - 5366.

8
[ 110761-07-4 ]
[ 100-39-0 ]
[ 56762-93-7 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 870 - 876.

9
[ 67-56-1 ]
[ 63-68-3 ]
[ 501-53-1 ]
[ 56762-93-7 ]

References: [1]Amino Acids,2010,vol. 39,p. 443 - 448.
[2]Tetrahedron,1994,vol. 50,p. 5569 - 5578.

10
[ 2491-18-1 ]
[ 501-53-1 ]
[ 56762-93-7 ]

References: [1]Synthetic Communications,1989,vol. 19,p. 3457 - 3468.
[2]European Journal of Organic Chemistry,2008,p. 3107 - 3112.
[3]Organic Syntheses,1992,vol. 70,p. 29 - 29.
[4]Journal of Organic Chemistry,1980,vol. 45,p. 4817 - 4820.
[5]Tetrahedron Letters,2010,vol. 51,p. 3226 - 3228.

11
[ 56762-93-7 ]
[ 598-41-4 ]
[ 15998-56-8 ]

References: [1]Collection of Czechoslovak Chemical Communications,1989,vol. 54,p. 2027 - 2041.

12
[ 56762-93-7 ]
[ 2748-02-9 ]
Z-Met-Leu-OtBu [ No CAS ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 2216 - 2226.

13
[ 67-56-1 ]
[ 1152-62-1 ]
[ 56762-93-7 ]

References: [1]Bulletin of the Chemical Society of Japan,1978,vol. 51,p. 1897 - 1898.

14
[ 56762-93-7 ]
[ 137649-65-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1975,vol. 23,p. 3081 - 3087.

15
[ 56762-93-7 ]
[ 10466-56-5 ]
[(S)-1-((1S,2S)-1-Carbamoyl-2-methyl-butylcarbamoyl)-3-methylsulfanyl-propyl]-carbamic acid benzyl ester [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1998,p. 319 - 325.

16
[ 75266-39-6 ]
[ 56762-93-7 ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 3781 - 3783.

17
[ 67-56-1 ]
[ 115481-99-7 ]
[ 56762-93-7 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5319 - 5321.

18
[ 10332-17-9 ]
[ 501-53-1 ]
[ 56762-93-7 ]

References: [1]Chemistry - A European Journal,2004,vol. 10,p. 544 - 553.
[2]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 325 - 328.
[3]Chemistry - A European Journal,2018,vol. 24,p. 8051 - 8055.

19
[ 50-00-0 ]
[ 56762-93-7 ]
[ 115481-99-7 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 7663 - 7665.

20
[ 67-56-1 ]
[ 127862-75-3 ]
(S)-2-Benzyloxycarbonylamino-4-methylsulfanyl-butyric acid 2,2,2-trifluoro-ethyl ester [ No CAS ]
(R)-2-Benzyloxycarbonylamino-4-methylsulfanyl-butyric acid 2,2,2-trifluoro-ethyl ester [ No CAS ]
[ 56762-93-7 ]

References: [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2569 - 2573.

21
[ 63-68-3 ]
[ 56762-93-7 ]

References: [1]Chemistry - A European Journal,2004,vol. 10,p. 544 - 553.
[2]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 325 - 328.
[3]Helvetica Chimica Acta,1951,vol. 34,p. 2085,2093.

22
[ 56762-93-7 ]
[ 60027-55-6 ]

References: [1]Chemistry - A European Journal,2004,vol. 10,p. 544 - 553.

23
[ 56762-93-7 ]
[ 75266-40-9 ]

References: [1]Chemistry - A European Journal,2004,vol. 10,p. 544 - 553.
[2]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 325 - 328.
[3]Synthetic Communications,1989,vol. 19,p. 3457 - 3468.
[4]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 893 - 901.
[5]Journal of the Chemical Society. Perkin transactions I,1992,p. 1149 - 1158.
[6]Journal of Organic Chemistry,1980,vol. 45,p. 4817 - 4820.
[7]Journal of Organic Chemistry,1980,vol. 45,p. 4817 - 4820.
[8]Patent: US9434762,2016,B2 .
[9]Organic Syntheses,1992,vol. 70,p. 29 - 29.

24
[ 56762-93-7 ]
[ 35677-89-5 ]

References: [1]Chemistry - A European Journal,2004,vol. 10,p. 544 - 553.

25
[ 56762-93-7 ]
(S)-2-Benzyloxycarbonylamino-4-(9-bora-bicyclo[3.3.1]non-9-yl)-butyric acid methyl ester [ No CAS ]

References: [1]Chemistry - A European Journal,2004,vol. 10,p. 544 - 553.

26
[ 56762-93-7 ]
(R)-2-Benzyloxycarbonylamino-4-phenanthren-9-yl-butyric acid methyl ester [ No CAS ]

References: [1]Chemistry - A European Journal,2004,vol. 10,p. 544 - 553.

27
[ 56762-93-7 ]
[ 10332-17-9 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 7663 - 7665.

28
[ 56762-93-7 ]
[ 41442-22-2 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 7663 - 7665.

29
[ 56762-93-7 ]
[ 1830-73-5 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 7663 - 7665.

30
[ 56762-93-7 ]
Sodium; (S)-2-benzyloxycarbonylamino-4-methylsulfanyl-butyrate [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 7663 - 7665.

31
[ 56762-93-7 ]
[ 115887-83-7 ]