[ CAS No. 887707-95-1 ] {[proInfo.proName]}

Name: 887707-95-1|Boc-Thr(Fmoc-Val)-OH|95%
Brand: Ambeed
SKU: A172314
Rating: 95 (40 reviews)

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Quality Control of [ 887707-95-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 887707-95-1 ]

SDS Specification

Alternatived Products of [ 887707-95-1 ]

Product Details of [ 887707-95-1 ]

CAS No. :	887707-95-1	MDL No. :	MFCD11974993
Formula :	C₂₉H₃₆N₂O₈	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KFMYXFZGGHKJMR-CQLNOVPUSA-N
M.W :	540.60	Pubchem ID :	11649564
Synonyms :

Calculated chemistry of [ 887707-95-1 ]

Physicochemical Properties

Num. heavy atoms :	39
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.45
Num. rotatable bonds :	15
Num. H-bond acceptors :	8.0
Num. H-bond donors :	3.0
Molar Refractivity :	143.85
TPSA :	140.26 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.34
Log Po/w (XLOGP3) :	5.11
Log Po/w (WLOGP) :	4.46
Log Po/w (MLOGP) :	2.59
Log Po/w (SILICOS-IT) :	3.67
Consensus Log Po/w :	3.83

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	2.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-5.65
Solubility :	0.00121 mg/ml ; 0.00000225 mol/l
Class :	Moderately soluble
Log S (Ali) :	-7.8
Solubility :	0.00000858 mg/ml ; 0.0000000159 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-6.25
Solubility :	0.000308 mg/ml ; 0.000000569 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	5.34

Safety of [ 887707-95-1 ]

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 [ 887707-95-1 ]

* 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 [ 887707-95-1 ]
Downstream synthetic route of [ 887707-95-1 ]

[ 887707-95-1 ] Synthesis Path-Upstream 1~3

1
[ 140422-54-4 ]
[ 887707-95-1 ]

Reference： [1] Tetrahedron Letters, 2006, vol. 47, # 18, p. 3013 - 3017

2
[ 2592-18-9 ]
[ 887707-95-1 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 2, p. 532 - 544

3
[ 545432-97-1 ]
[ 887707-95-1 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 2, p. 532 - 544

[ 887707-95-1 ] Synthesis Path-Downstream 1~21

1
Boc-Thr(Fmoc-Val)-OBzl [ No CAS ]
[ 887707-95-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	palladium on activated charcoal; In ethyl acetate; for 3.0h;	Then to Boc-Thr(Fmoc-Val)-OBzl (236mg, 0.374mmol) in AcOEt (10mL) was added Pd/C (12 mg) and the mixture was vigorously stirred for 3 hours. After removal of Pd/C through Celite, the solvent was concentrated in vacuo, filtered by silica gel (AcOEt: hexane 1:2) and washed with MeOH to give objective Boc-Thr(Fmoc-Val)-OH (3a) with high purity (186 mg, 0.346mmol, yield 92%). HRMS (FAB): calcd. for C29H36N2O8Na (M+Na)+: 563.2369, found: 563.2373; HPLC analysis at 230 nm: purity 95% or more; NMR (CD3OD, 400 MHz): delta 7.79 (d, 3J(H,H) = 7.3 Hz, 2 H, CH), 7.75-7.66 (m, 2H, CH), 7.38 (t, 3J(H,H) = 7.5 Hz, 2 H, CH), 7.33-7.29 (m, 2H, CH), 5.44-5.41 (m, 1H, CH), 4.38 (d, 3J(H,H) = 7.0 Hz, 2 H, CH2), 4.25-4.22 (m, 2 H, CH), 4.05-4.01 (m, 1 H, CH), 2.11-2.02 (m, 1 H, CH), 1.44 (s, 9 H, CH3), 1.25 (d, 3J(H,H) = 6.4 Hz, 3 H, CH3), 0.91, 0.89 (2d, 3J(H,H) = 7.7, 7.0 Hz, 6 H, CH3).

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3013 - 3017
[2]Patent: EP1992611,2008,A1 .Location in patent: Page/Page column 6

2
[ 887707-95-1 ]
[ 68858-20-8 ]
[ 108-24-7 ]
[ 76-05-1 ]
H-Val-Val-NH-resin [ No CAS ]
(S)-2-((S)-2-Acetylamino-3-methyl-butyrylamino)-3-methyl-butyric acid (1R,2S)-2-amino-2-[(S)-1-((S)-1-carbamoyl-2-methyl-propylcarbamoyl)-2-methyl-propylcarbamoyl]-1-methyl-ethyl ester; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3013 - 3017

3
[ 887707-95-1 ]
[ 68858-20-8 ]
[ 108-24-7 ]
Boc-Thr(Ac-Val-Val)-OH [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 7905 - 7909

4
[ 887707-95-1 ]
(S)-2-((S)-2-Acetylamino-3-methyl-butyrylamino)-3-methyl-butyric acid (1R,2S)-2-amino-2-[(S)-1-((S)-1-carbamoyl-2-methyl-propylcarbamoyl)-2-methyl-propylcarbamoyl]-1-methyl-ethyl ester; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 7905 - 7909

5
[ 68858-20-8 ]
Fmoc-Pro-OH [ No CAS ]
[ 887707-95-1 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3013 - 3017

6
[ 140422-54-4 ]
[ 887707-95-1 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3013 - 3017

7
[ 887707-95-1 ]
C₁₀H₂₀N₃O₂Pol [ No CAS ]
C₃₉H₅₄N₅O₉Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; for 2.0h;	Example 3; Synthesis of Ac-Val-Val-Thr-Val-Val-NH2 (3a); Using Rink Amide AM resin (100mg, 0.071mmol), after washing this resin with DMF (1.5mL×5), according to the sequence by using Fmoc-Val-OH there was constructed H-Val-Val-NH-resin by the conventional method. This product was condensed with <strong>[887707-95-1]Boc-Thr(Fmoc-Val)-OH</strong> (100mg, 0.18mmol) which was synthesized by example 1 in DMF (1.5mL) in the presence of 1,3-diisopropylcarbodiimide (29.0muL, 0.18mmol) and 1-hydroxybenzotriazole (28.4mg, 0.18mmol). Then after introducing Fmoc-Val-OH (62.8mg, 0.18mmol) thereto, N-acetylation was carried out by using Ac2O (10.5muL, 0.11mmol)-triethylamine (10.4muL, 0.071mmol). The protected peptide resin was stirred under the presence of thioanisole (66.7mul), m-cresol (66.7mul) and water (66.7muL) in TFA (2.47mL) for 90 minutes. The reaction solution was concentrated, washed with Et2O, suspended in water and lyophilized to give O-acyl isopeptide (4a) of the following formula: [Show Image] as white amorphous powders (21.2 mg, yield 44.5%). HRMS (FAB): calcd for C26H49N6O7 (M+H)+: 557.3663, found: 557.3666; HPLC analysis at 230 nm: purity 95% or more.

Reference： [1]Patent: EP1992611,2008,A1 .Location in patent: Page/Page column 5; 6

8
[ 2592-18-9 ]
[ 887707-95-1 ]