[ CAS No. 135273-01-7 ]

Name: 135273-01-7|(2R,2'R)-3,3'-Disulfanediylbis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoic acid)|96%
Brand: Ambeed
SKU: A884411
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Quality Control of [ 135273-01-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 135273-01-7 ]

SDS Specification

Alternatived Products of [ 135273-01-7 ]

Product Details of [ 135273-01-7 ]

CAS No. :	135273-01-7	MDL No. :	MFCD00237447
Formula :	C₃₆H₃₂N₂O₈S₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IRQYKZZFOSDZHP-ACHIHNKUSA-N
M.W :	684.78 g/mol	Pubchem ID :	14389776
Synonyms :

Calculated chemistry of [ 135273-01-7 ]

Physicochemical Properties

Num. heavy atoms :	48
Num. arom. heavy atoms :	24
Fraction Csp3 :	0.22
Num. rotatable bonds :	17
Num. H-bond acceptors :	8.0
Num. H-bond donors :	4.0
Molar Refractivity :	183.41
TPSA :	201.86 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.31
Log Po/w (XLOGP3) :	5.83
Log Po/w (WLOGP) :	6.35
Log Po/w (MLOGP) :	3.47
Log Po/w (SILICOS-IT) :	5.03
Consensus Log Po/w :	4.8

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	2.0
Egan :	2.0
Muegge :	4.0
Bioavailability Score :	0.11

Water Solubility

Log S (ESOL) :	-7.01
Solubility :	0.0000675 mg/ml ; 0.0000000985 mol/l
Class :	Poorly soluble
Log S (Ali) :	-9.84
Solubility :	0.000000099 mg/ml ; 0.0000000001 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-9.78
Solubility :	0.000000114 mg/ml ; 0.0000000002 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	5.46

Safety of [ 135273-01-7 ]

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 [ 135273-01-7 ]

* 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.

Upstream synthesis route of [ 135273-01-7 ]
Downstream synthetic route of [ 135273-01-7 ]

[ 135273-01-7 ] Synthesis Path-Upstream 1~11

1
[ 135273-01-7 ]
[ 103213-32-7 ]

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

2
[ 135273-01-7 ]
[ 67436-13-9 ]

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

3
[ 135273-01-7 ]
[ 53298-33-2 ]

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

4
[ 135273-01-7 ]
[ 86060-81-3 ]

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

5
[ 135273-01-7 ]
[ 73724-43-3 ]

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

6
[ 135273-01-7 ]
[ 136050-67-4 ]

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

7
[ 56-89-3 ]
[ 28920-43-6 ]
[ 135273-01-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium carbonate In 1,4-dioxane; water at 10 - 20℃; for 2 h;	Sodium carbonate (4.6 g, 43.6 mmol) and L-cystine (5.0 g, 20.8 mmol) were dissolved in water (200 mL). The resulting solution was cooled to 10° C. FmocCl (11.85 g, 45.8 mmol) was dissolved in dioxane (80 mL), and the resulting solution was added dropwise to the aqueous solution of L-cystine. The solution was stirred for 2 h at 10° C. and allowed to gradually warm to room temperature. A thick white precipitate was obtained that was filtered onto a sintered glass funnel. The product was triturated with diethyl ether (50 mL) and dried in vacuuo for 2 d. N,N'-Bis(Fmoc)-L-cystine (14.0 g, 98percent yield) was obtained as a white powder.

Reference： [1] Patent: US2007/37963, 2007, A1, . Location in patent: Page/Page column 11-12; Figure 4

8
[ 56-89-3 ]
[ 82911-69-1 ]
[ 135273-01-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium carbonate In water; acetone at 50℃;	General procedure: Procedure adapted from that of Agan et al[28]. 407 mg Na₂CO₃ (3.82 mmol) was dissolved in 30 mL distilled water with stirring. 35 mL acetone was then added followed by 1.91 mmol L-cystine or L-selenocystine. The temperature of the reaction was brought to 50 °C and 1.93g (5.73 mmol) Fmoc-OSu was added in portions over 5 minutes. Heating was removed and the reaction was allowed to progress overnight. At the end of this time, 40 mL 1 HCl was added followed by 50 mL EtOAc. Following vigorous shaking, the layers were separated, and the organic portionwas dried over MgSO₄ and concentrated in vacuo to afford the crude bis N-Fmoc dichalcogenide which was purified by recrystallization from CHCl₃.

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

9
[ 86060-81-3 ]
[ 135273-01-7 ]

Reference： [1] Chemical Communications, 2014, vol. 50, # 71, p. 10295 - 10298

10
[ 103213-32-7 ]
[ 135273-01-7 ]

Reference： [1] Biopolymers, 2017, vol. 108, # 2,

11
[ 135248-89-4 ]
[ 135273-01-7 ]

Reference： [1] New Journal of Chemistry, 2015, vol. 39, # 10, p. 7750 - 7753

[ 135273-01-7 ] Synthesis Path-Downstream 1~59

1
[ 135273-01-7 ]
[ 135248-89-4 ]

Yield	Reaction Conditions	Operation in experiment
73%	With trifluoroacetic acid; zinc; In methanol; at 20℃; for 14.0h;	N,N'-Bis(Fmoc)-L-cystine (12.0 g, 17.5 mmol) was dissolved in methanol (300 mL). Granular zinc (12.0 g) was added to this solution and the resulting mixture was vigorously stirred using a magnetic stirrer. Trifluoroacetic acid (75 mL, 1 mol) was added dropwise into the reaction mixture, over period of 2 h and stirred at room temperature for a period of 12 h. The reaction was monitored by C-18 reverse phase high pressure liquid chromatography (HPLC) and thin layer chromatography (TLC, chloroform/methanol/acetic acid=30:1:0.1, v/v). Upon disappearance of <strong>[135273-01-7]N,N'-bis(Fmoc)-L-cystine</strong>, the reaction mixture was filtered and concentrated on a rotary evaporator to reduce the volume to approximately 100 mL. Dichloromethane (400 mL) was added and the mixture was washed with 2N aqueous hydrochloric acid. The aqueous layer was extracted with dichloromethane and the combined organic layers were dried over magnesium sulfate. Concentration of the solution gave N-(Fmoc)-L-cysteine, 8.8 g 73%) (FIGS. 3 and 4, structure B) as a white powder.

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 3841 - 3848
[2]Patent: US2007/37963,2007,A1 .Location in patent: Page/Page column 12; Figure 4
[3]Tetrahedron,1995,vol. 51,p. 5643 - 5656
[4]Tetrahedron Asymmetry,1997,vol. 8,p. 1453 - 1465
[5]Protein and Peptide Letters,2014,vol. 21,p. 1257 - 1264

2
[ 104-01-8 ]
[ 71989-31-6 ]
[ 73724-45-5 ]
[ 135273-01-7 ]
(5S,8R,13R,15aS)-8-[(S)-2-Amino-3-(4-methoxy-phenyl)-3-oxo-propionylamino]-5-hydroxymethyl-4,7,15-trioxo-tetradecahydro-10,11-dithia-3a,6,14-triaza-cyclopentacyclotetradecene-13-carboxylic acid [ No CAS ]