[ CAS No. 67436-13-9 ] {[proInfo.proName]}

Name: 67436-13-9|Fmoc-Cys(tBu)-OH|98%
Brand: Ambeed
SKU: A163032
Price: 5.0 USD
Availability: InStock
Rating: 93 (30 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 67436-13-9 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 67436-13-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 67436-13-9 ]

SDS Specification

Alternatived Products of [ 67436-13-9 ]

Product Details of [ 67436-13-9 ]

CAS No. :	67436-13-9	MDL No. :	MFCD00037130
Formula :	C₂₂H₂₅NO₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IXAYZHCPEYTWHW-IBGZPJMESA-N
M.W :	399.50	Pubchem ID :	7009544
Synonyms :		Chemical Name :	Fmoc-Cys(tBu)-OH

Calculated chemistry of [ 67436-13-9 ]

Physicochemical Properties

Num. heavy atoms :	28
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.36
Num. rotatable bonds :	9
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	112.03
TPSA :	100.93 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.55
Log Po/w (XLOGP3) :	4.32
Log Po/w (WLOGP) :	4.51
Log Po/w (MLOGP) :	3.22
Log Po/w (SILICOS-IT) :	3.92
Consensus Log Po/w :	3.7

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.76
Solubility :	0.00692 mg/ml ; 0.0000173 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.15
Solubility :	0.00028 mg/ml ; 0.000000702 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-6.17
Solubility :	0.000269 mg/ml ; 0.000000673 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	4.33

Safety of [ 67436-13-9 ]

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 [ 67436-13-9 ]

* 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 [ 67436-13-9 ]
Downstream synthetic route of [ 67436-13-9 ]

[ 67436-13-9 ] Synthesis Path-Upstream 1~5

1
[ 35661-60-0 ]
[ 67436-13-9 ]
[ 115057-30-2 ]
[ 71989-31-6 ]
[ 50-56-6 ]

Reference： [1] Tetrahedron Letters, 1987, vol. 28, # 46, p. 5651 - 5654

2
[ 28920-43-6 ]
[ 2481-09-6 ]
[ 67436-13-9 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 2057 - 2064

3
[ 135273-01-7 ]
[ 67436-13-9 ]

Reference： [1] Protein and Peptide Letters, 2014, vol. 21, # 12, p. 1257 - 1264

4
[ 82911-69-1 ]
[ 67436-13-9 ]

Reference： [1] Protein and Peptide Letters, 2014, vol. 21, # 12, p. 1257 - 1264

5
[ 135248-89-4 ]
[ 75-65-0 ]
[ 67436-13-9 ]

Reference： [1] Protein and Peptide Letters, 2014, vol. 21, # 12, p. 1257 - 1264

[ 67436-13-9 ] Synthesis Path-Downstream 1~88

1
[ 54714-11-3 ]
[ 67436-13-9 ]
[ 113534-23-9 ]

Reference： [1]Liebigs Annalen der Chemie,1988,p. 437 - 440

2
[ 68206-45-1 ]
[ 67436-13-9 ]
[ 82176-99-6 ]

Reference： [1]Chemistry Letters,1982,p. 921 - 924

3
[ 28920-43-6 ]
[ 2481-09-6 ]
[ 67436-13-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 2057 - 2064

4
[ 209604-83-1 ]
[ 79598-53-1 ]
[ 67436-13-9 ]
3-(6-azido-hexanoylamino)-5-[3-tert-butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-methyl}-benzoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6288 - 6306

5
[ 167215-64-7 ]
[ 605-65-2 ]
[ 67436-13-9 ]
3-[3-tert-butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-methyl}-5-(5-dimethylamino-naphthalene-1-sulfonylamino)-benzoic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6288 - 6306

6
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-33-8 ]
[ 67436-13-9 ]
Fmoc-Val-OHFmoc-Arg(Pbf)-OH [ No CAS ]
H-Cys-Leu-Val-Ala-Ile-Ser-Ala-Arg-Tyr-Trp-NH₂ [ No CAS ]

Reference： [1]Journal of Mass Spectrometry,2006,vol. 41,p. 1470 - 1483

7
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-33-8 ]
[ 67436-13-9 ]
Fmoc-Val-OHFmoc-Arg(Pbf)-OH [ No CAS ]
H-Cys-Leu-Val-Ala-Ile-Ser-Ala-Arg-Tyr-Trp-OH [ No CAS ]

Reference： [1]Journal of Mass Spectrometry,2006,vol. 41,p. 1470 - 1483

8
[ 67436-13-9 ]
Fmoc-Cys(S-tBu)-HES [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With benzotriazol-1-ol; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; at 21 - 22℃; for 19.5h;	86.3 mg Fmoc-Cys (S-tBu) -OH (Fluka, Sigma-Aldrich Chemie GmbH, Taufkirchen, D) and 45.9 mg 1-hydroxy-1H-benzotriazole (Aldrich, Sigma-Aldrich Chemie GmbH, Taufkirchen, D) were dissolved in 2 mL N, N-dimethylforinamide (Peptide synthesis grade, Biosolve, Valkenswaard, NL), and 40. 7 uL N, N'-diisopropylcarbodiimide (Fluka, Sigma- Aldrich Chemie GmbH, Taufkirchen, D) were added. After incubation at 21 C for 30 min, 206 mg of amino-HES, synthesized as described in example 1. 1, were added. After shaking for 19 h at 22 C, the reaction mixture was added to 14 mL of ice-cold 2-propanol (Carl Roth GmbH, Karlsruhe, D). The precipitated product was collected by centrifugation at 4 C, re-suspended in 8 ml 2-propanol and centrifuged as described. The precipitate was dissolved in 20 mL water, 20 ml dichloromethane (Carl Roth GmbH, Karlsruhe, D) were added and the mixture was vortexed. After centrifugation, the upper aqueous layer was isolated, dialysed for 43 h against water (SnakeSkin dialysis tubing, 3.5 kD cut off, Perbio Sciences Deutschland GmbH, Bonn, D) and lyophilized. Fmoc-Cys (S-tBu) -HES was isolated in 67 % yield. 100.7 mg of Fmoc-Cys (S-tBu) -HES was dissolved in 1 mL of 20 % piperidine (Acros Organics, Geel, B) in DMF (v/v). After shaking for 15 min at 22 C, the reaction mixture was added to 20 mL of tert-butyl methyl ether (Acros Organics, Geel, B). The precipitated product was collected by centrifugation at 4 C, re-suspended in 10 ml tert-butyl methyl ether and centrifuged. After drying, the precipitate was dissolved in 10 mL water and dialysed for 31 h against water (SnakeSkin dialysis tubing, 3.5 kD cut off, Perbio Sciences Deutschland GmbH, Bonn, D) and lyophilized. H-Cys (S-tBu) -HES was isolated in 80% yield.

Reference： [1]Patent: WO2005/92391,2005,A2 .Location in patent: Page/Page column 48

9
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 67436-13-9 ]
[ 71989-20-3 ]
Asn(Trt)-Cys(Trt)-((3R)-1,2,3,4-tetrahydroisoquinolin-3-ylcarbonyl)-Leu-Gly-(Rink-Bernatowitz linker)-(2-chlorotrityl chloride resin) [ No CAS ]
NH₄SCH₂CHCONHCHCH₂C₆H₄OHCONH(CH)2CH₂(CH₃)2CONHCH(CH₂)2CONH₂CONHCHCH₂CONH₂CONHCHCH₂SCONC₉H₉CONHCHCH₂CH(CH₃)2CONHCH₂CONH₂ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 799 - 806

10
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 67436-13-9 ]
[ 71989-20-3 ]
Asn(Trt)-Cys(Trt)-((3S)-1,2,3,4-tetrahydroisoquinolin-3-ylcarbonyl)-Leu-Gly-(Rink-Bernatowitz linker)-(2-chlorotrityl chloride resin) [ No CAS ]
NH₄SCH₂CHCONHCHCH₂C₆H₄OHCONH(CH)2CH₂(CH₃)2CONHCH(CH₂)2CONH₂CONHCHCH₂CONH₂CONHCHCH₂SCONC₉H₉CONHCHCH₂CH(CH₃)2CONHCH₂CONH₂ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 799 - 806

11
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 67436-13-9 ]
[ 71989-20-3 ]
Asn(Trt)-Cys(Trt)-(S)-NHCH(t-Bu)CO-Leu-Gly-(Rink-Bernatowitz linker)-(2-chlorotrityl chloride resin) [ No CAS ]
NH₄SCH₂CHCONHCHCH₂C₆H₄OHCONH(CH)2CH₂(CH₃)2CONHCH(CH₂)2CONH₂CONHCHCH₂CONH₂CONHCHCH₂SCONC₅H₁₁CONHCHCH₂CH(CH₃)2CONHCH₂CONH₂ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 799 - 806

12
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 67436-13-9 ]
[ 71989-20-3 ]
Asn(Trt)-Cys(Trt)-(S)-piperidin-3-ylcarbonyl-Leu-Gly-(Rink-Bernatowitz linker)-(2-chlorotrityl chloride resin) [ No CAS ]
NH₄SCH₂CHCONHCHCH₂C₆H₄OHCONH(CH)2CH₂(CH₃)2CONHCH(CH₂)2CONH₂CONHCHCH₂CONH₂CONHCHCH₂SCONC₅H₉CONHCHCH₂CH(CH₃)2CONHCH₂CONH₂ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 799 - 806

13
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 67436-13-9 ]
[ 71989-20-3 ]
Asn(Trt)-Cys(Trt)-NH(CH₂)3CO-Leu-Gly-(Rink-Bernatowitz linker)-(2-chlorotrityl chloride resin) [ No CAS ]
NH₄SCH₂CHCONHCHCH₂C₆H₄OHCONH(CH)2CH₂(CH₃)2CONHCH(CH₂)2CONH₂CONHCHCH₂CONH₂CONHCHCH₂SCONHC₃H₆CONHCHCH₂CH(CH₃)2CONHCH₂CONH₂ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 799 - 806

14
[ 71989-23-6 ]
[ 67436-13-9 ]
[ 71989-20-3 ]
[ 132684-60-7 ]
Asn(Trt)-Cys(Trt)-(S)-NHCH(t-Bu)CO-Leu-Gly-(Rink-Bernatowitz linker)-(2-chlorotrityl chloride resin) [ No CAS ]
NH₄SCH₂CHCONHCHCH₂C₆H₄OHCONHCHC(CH₃)3CONHCH(CH₂)2CONH₂CONHCHCH₂CONH₂CONHCHCH₂SCONC₅H₁₁CONHCHCH₂CH(CH₃)2CONHCH₂CONH₂ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 799 - 806

15
[ 67436-13-9 ]
[ 256370-81-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 2967 - 2975

16
lysine(ε-Boc)-Rink-amide resin [ No CAS ]
[ 29022-11-5 ]
[ 35661-40-6 ]
[ 71989-14-5 ]
[ 103213-32-7 ]
[ 67436-13-9 ]
[ 119831-72-0 ]
(S)-6-[(Diphenyl-p-tolyl-methyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid [ No CAS ]
C₁₂₉H₁₆₃N₁₆O₁₉PolS₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The peptidyl resin corresponding to the above sequence was assembled by standard solid-phase peptide chemistry (Barany, G; Kneib- Cordonier, N; Mullenm D.G. (1987) Int. J. Peptide Protein Research 30, 705-739) on a Rink Amide MBHA resin (0.73 mmol/g; from NovaBiochem). An Applied Biosystems (Perkin Elmer) model 433A peptide synthesizer was used. The residues (from the carboxyl terminus) were assembled on a 0.25 mmol scale using single couplings with a 4-fold molar excess of Nalpha-Fmoc-protected amino acids (1 mmol cartridges) and 2-(1 H-benzotriazol-1-yl)- 1 ,1 ,3,3-tetramethyluronium-hexafluorophosphate (HBTU)/1-hydroxy-benzotriazole EPO <DP n="19"/>(HOBt)/diisopropylethyl-amine (DIEA) in N-methylpyrrolidone (NMP) using 2.5 hours coupling cycles. Fmoc-deprotection was achieved with conductivity monitoring using 20% piperidine in NMP. The amino acid-side chain protecting groups used were 4- methyltrityl (Mtt) for Lys1, terf-butyl (.Bu) for Cys2, Cys6 and Asp, 2,2,5,7,8- pentamethylchroman-6-sulfonyl (Pmc) for Arg, trityl (Trt) for Cys8, and tert- butyloxycarbonyl (Boc) for Lys10.

Reference： [1]Patent: WO2006/54904,2006,A2 .Location in patent: Page/Page column 17

17
[ 955095-35-9 ]
[ 67436-13-9 ]
C₈₅H₁₂₅Cl₂NO₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		An amount of 294 mg (0.3 mmol) of compound 16 were dissolved in 5 ml of dichloromethane, and 1 ml of acetyl chloride was added and reacted for 1 hour at 45C. After confirming the completion of the reaction by thin layer chromatography, vacuum distillation was carried out and the solvent was distilled, and a crystalline substance (compound 17) was obtained. The thus obtained crystals were dissolved in 10 ml of dichloromethane, and 180 mg (1.5 equivalents) of Fmoc-Cys(tBu)-OH, and 262 mul (5 equivalents) of diisopropylethylamine were added and reacted for 30 min at 0C. After confirming the completion of the reaction by thin layer chromatography, 500 mul of diazabicycloundecene were added, and further reacted for 10 minutes. After again confirming the completion of the reaction by thin layer chromatography, 100 ml of acetonitrile was added, and the solution was gradually vacuum filtered and crystals were precipitated, and suction filtration was carried out using a separatory funnel and a crystalline substance was obtained. The thus obtained crystalline substance was dissolved in 10 ml of dichloromethane, and 175 mg (1.5 equivalents) of Fmoc-Phe-OH, 188 mul (4 equivalents) of diisopropylcarbodiimide, and 162 mg (4 equivalents) of 1-hydroxybenzotriazole were added and reacted for 1 hr at room temperature. After confirming the completion of the reaction by thin layer chromatography, 100 ml of acetonitrile were added, and the solvent was gradually vacuum distilled and crystals were precipitated, and suction filtration was carried out using a separatory funnel and 371 mg of compound 18 were obtained. The yield was 83%. The thus obtained crystalline substance was dissolved in 10 ml of a previously adjusted 0.1% trifluoroacetic acid/dichloromethane solution and reacted for 1 hour. After confirming the completion of the reaction by thin layer chromatography, 100 ml of acetonitrile were added, and the solution was gradually vacuum distilled and crystals were precipitated, and suction filtration was carried out using a separatory funnel. By vacuum distillation of the obtained solution, the desired compound Fmoc-Phe-Cys(tBu)-OH (compound 19) was obtained. Further, confirmation of the desired product was carried out in a mass spectrograph. Compound 17;chloro-3,5-bis(docosyloxy)phenyl-4,4-dichlorophnylmethane

Reference： [1]Patent: EP2003104,2008,A2 .Location in patent: Page/Page column 24

18
C₆₁H₈₇N₉O₁₉PPol [ No CAS ]
[ 67436-13-9 ]
C₈₃H₁₁₀N₁₀O₂₂PPolS [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 10474 - 10475

19
[ 1606-67-3 ]
[ 29022-11-5 ]
[ 35661-39-3 ]
[ 935-13-7 ]
[ 67436-13-9 ]
[ 1126452-20-7 ]

Reference： [1]Chemical Communications,2009,p. 340 - 342

20
[ 55750-53-3 ]
[ 125741-64-2 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 71989-31-6 ]
[ 71989-28-1 ]
[ 67436-13-9 ]
MIC-Gly-Cys(StBu)-Met-Gly-Leu-Pro-Cys(Far)OMe [ No CAS ]