Home Cart 0 Sign in  

[ CAS No. 133852-23-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 133852-23-0
Chemical Structure| 133852-23-0
Structure of 133852-23-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 133852-23-0 ]

Related Doc. of [ 133852-23-0 ]

Alternatived Products of [ 133852-23-0 ]

Product Details of [ 133852-23-0 ]

CAS No. :133852-23-0 MDL No. :MFCD20264831
Formula : C28H29NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :VJSGNJOUWWMJDE-VWLOTQADSA-N
M.W : 459.53 Pubchem ID :15295906
Synonyms :

Calculated chemistry of [ 133852-23-0 ]

Physicochemical Properties

Num. heavy atoms : 34
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.29
Num. rotatable bonds : 10
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 130.46
TPSA : 84.86 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.27
Log Po/w (XLOGP3) : 5.6
Log Po/w (WLOGP) : 5.18
Log Po/w (MLOGP) : 3.69
Log Po/w (SILICOS-IT) : 5.01
Consensus Log Po/w : 4.55

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.95
Solubility : 0.000517 mg/ml ; 0.00000112 mol/l
Class : Moderately soluble
Log S (Ali) : -7.14
Solubility : 0.000033 mg/ml ; 0.0000000717 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.26
Solubility : 0.00000252 mg/ml ; 0.0000000055 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.47

Safety of [ 133852-23-0 ]

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 [ 133852-23-0 ]

* 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 [ 133852-23-0 ]
  • Downstream synthetic route of [ 133852-23-0 ]

[ 133852-23-0 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 16874-12-7 ]
  • [ 82911-69-1 ]
  • [ 133852-23-0 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 18 h;
Stage #2: With hydrogenchloride; water In 1,4-dioxane
[00284] tButyl N-(9-fluorenylmethoxycarbonyl)-L-tyrosine (83): To a stirring suspension of L-tyrosine O-f-butyl ester (LOOg, 4.21 mmol) and NaHCO3 (354 mg, 4.21 mmol) in 1 ,4-dioxane/water (1 :1 , 20 ml_) was added 9-fluorenylmethyl-N-succinimidyl carbonate (1.42 g, 4.21 mmol) and the resulting mixture was stirred for 18 hr at room temperature. The solvent was reduced to 10 ml. followed by the addition of 50 ml. of cold 1 N HCl. The product was extracted with ethyl acetate (3x). The organic extracts were washed with H2O and saturated aqueous NaCl then dried over Na2SO4. The solution was then concentrated after filtration to give the colourless solid 83 (1.94 g, 100percent) which was used without purification: 1H NMR (400 MHz, CDCI3) δ 1.43 (s, 9H), 2.97-3.06 (m, 2H), 4.21 (bt, J=7.1 , 1 H), 4.33 (dd, J=7.1 , 10.5, 1 H), 4.41-4.53 (m, 2H), 5.01 (bs, 1 H), 5.30, (d, J=8.2, 1 H), 6.73 (d, J=8.5, 2H), 7.00 (d, J=8.5, 2H), 7.31 (t, J=7.5, 2H), 7.40 (t, J=7.5, 2H), 7.57 (dd, J=3.3, 7.3, 2H), 7.76 (d, J=7.5, 2H).
95.8% With N-ethyl-N,N-diisopropylamine In acetone at 20℃; for 12 h; 10 mmol of L-tyrosine tert-butyl ester and10 molecules of N, N-diisopropylethylamine were dissolved in 75 mL of acetone,A 75 mL portion of acetone solution containing 9.8 mmol of Fmoc-OSu was added under stirring,Stirred at room temperature for 12 hours,And then separated by silica gel column chromatography,To obtain 4.4 g of product Fmoc-L-Tyr-OtBu (i.e., compound 3 in the above synthesis step)The yield was 95.8percent
Reference: [1] Patent: WO2010/19511, 2010, A2, . Location in patent: Page/Page column 125-126
[2] Chemical Communications, 2011, vol. 47, # 15, p. 4439 - 4441
[3] Patent: CN104274839, 2017, B, . Location in patent: Paragraph 0036; 0038; 0040; 0041
[4] Angewandte Chemie - International Edition, 2009, vol. 48, # 11, p. 2024 - 2026
[5] Tetrahedron Letters, 1995, vol. 36, # 27, p. 4733 - 4736
[6] Chinese Journal of Chemistry, 2012, vol. 30, # 1, p. 53 - 58
  • 2
  • [ 98946-18-0 ]
  • [ 112883-29-1 ]
  • [ 133852-23-0 ]
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 3, p. 1041 - 1047
[2] Journal of Organic Chemistry, 2003, vol. 68, # 17, p. 6795 - 6798
  • 3
  • [ 82911-69-1 ]
  • [ 133852-23-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 9, p. 1383 - 1386
  • 4
  • [ 28920-43-6 ]
  • [ 16874-12-7 ]
  • [ 133852-23-0 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 40, p. 9472 - 9476
  • 5
  • [ 98946-18-0 ]
  • [ 112883-29-1 ]
  • [ 133852-23-0 ]
  • [ 129460-19-1 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 12, p. 1557 - 1560
[2] Tetrahedron Letters, 1998, vol. 39, # 12, p. 1557 - 1560
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 133852-23-0 ]

Amino Acid Derivatives

Chemical Structure| 82911-79-3

[ 82911-79-3 ]

(S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate

Similarity: 0.95

Chemical Structure| 18938-60-8

[ 18938-60-8 ]

Boc-Tyr-OtBu

Similarity: 0.95

Chemical Structure| 72594-77-5

[ 72594-77-5 ]

(S)-Ethyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate

Similarity: 0.95

Chemical Structure| 118488-18-9

[ 118488-18-9 ]

Fmoc-D-Tyr(tBu)-OH

Similarity: 0.94

Chemical Structure| 71989-38-3

[ 71989-38-3 ]

Fmoc-Tyr(tBu)-OH

Similarity: 0.94