Home Cart 0 Sign in  

[ CAS No. 105047-45-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 105047-45-8
Chemical Structure| 105047-45-8
Structure of 105047-45-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 105047-45-8 ]

Related Doc. of [ 105047-45-8 ]

Alternatived Products of [ 105047-45-8 ]

Product Details of [ 105047-45-8 ]

CAS No. :105047-45-8 MDL No. :MFCD00038539
Formula : C21H24N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :YRKFMPDOFHQWPI-IBGZPJMESA-N
M.W : 368.43 Pubchem ID :7010557
Synonyms :

Calculated chemistry of [ 105047-45-8 ]

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.33
Num. rotatable bonds : 10
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 102.3
TPSA : 101.65 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 0.54
Log Po/w (WLOGP) : 3.11
Log Po/w (MLOGP) : 2.19
Log Po/w (SILICOS-IT) : 2.89
Consensus Log Po/w : 2.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.13
Solubility : 2.71 mg/ml ; 0.00736 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 2.09 mg/ml ; 0.00567 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.73
Solubility : 0.000684 mg/ml ; 0.00000186 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.67

Safety of [ 105047-45-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 105047-45-8 ]

* 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 [ 105047-45-8 ]
  • Downstream synthetic route of [ 105047-45-8 ]

[ 105047-45-8 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 105047-45-8 ]
  • [ 2937-50-0 ]
  • [ 146982-27-6 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With potassium carbonate In 1,4-dioxane; water at 23℃; for 20 h;
Stage #2: With hydrogenchloride In water
Example L1c
(S)-6-Allyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid
The solution of 25 g (61.7 mmol) of (S)-6-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid in 275 ml of dioxane is mixed with 25 ml of a 25percent potassium carbonate solution, and 6.55 ml of allyl chloroformate is added.
It is stirred for 20 hours at 23° C., diluted with water and extracted with methyl-tert-butyl ether.
The separated aqueous phase is acidified with a 2N hydrochloric acid and extracted several times with dichloromethane.
The combined dichloromethane phases are dried on sodium sulfate.
After filtration and removal of the solvent, 26.3 g (58.1 mmol, 94percent) of the title compound, which is further reacted without purification, is isolated.
Reference: [1] Patent: US2005/234247, 2005, A1, . Location in patent: Page/Page column 15
[2] ChemBioChem, 2010, vol. 11, # 8, p. 1083 - 1092
  • 2
  • [ 1755-15-3 ]
  • [ 105047-45-8 ]
  • [ 150629-67-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9290 - 9298
[2] Journal of the Chemical Society, Chemical Communications, 1993, # 9, p. 778 - 779
  • 3
  • [ 94142-97-9 ]
  • [ 105047-45-8 ]
  • [ 150629-67-7 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 12, p. 1603 - 1606
  • 4
  • [ 108-24-7 ]
  • [ 105047-45-8 ]
  • [ 159766-56-0 ]
Reference: [1] Molecular Cancer Therapeutics, 2017, vol. 16, # 1, p. 116 - 123
  • 5
  • [ 105047-45-8 ]
  • [ 172611-72-2 ]
  • [ 204777-78-6 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 12, p. 1603 - 1606
  • 6
  • [ 105047-45-8 ]
  • [ 14470-28-1 ]
  • [ 159857-60-0 ]
Reference: [1] Patent: US2005/54607, 2005, A1, . Location in patent: Page/Page column 17
  • 7
  • [ 105047-45-8 ]
  • [ 407-25-0 ]
  • [ 76265-69-5 ]
Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 41, p. 13586 - 13591
  • 8
  • [ 105047-45-8 ]
  • [ 35013-72-0 ]
  • [ 146987-10-2 ]
Reference: [1] Chemical Communications, 2006, # 7, p. 717 - 719
[2] Chemical Communications, 2017, vol. 53, # 36, p. 5020 - 5023
[3] Chemistry - A European Journal, 2017, vol. 23, # 45, p. 10906 - 10914
  • 9
  • [ 105047-45-8 ]
  • [ 58-85-5 ]
  • [ 146987-10-2 ]
Reference: [1] Journal of Chemical Research, 2010, # 6, p. 348 - 350
  • 10
  • [ 105047-45-8 ]
  • [ 159610-89-6 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With imidazole-1-sulfonyl azide hydrochloride; potassium carbonate In methanol at 20℃;
Stage #2: With hydrogenchloride In dichloromethane; water
Fmoc-lysine (2.03 g, 5.51 mmol), CuSO4 (88 mg, 0.35 mmol) and K2CO3 (2.46 g, 17.83 mmol) were dissolved in MeOH (70 mL). Imidazole-1-sulfonyl azide hydrochloride (3, 1.40 g, 6.70 mmol) was added in small portions and the suspension was stirred overnight at room temperature. The solvent was evaporated in vacuo, and the residue was redissolved in CH2Cl2 (50 mL). The solution was washed with aqueous HCl (1 M, 50 mL), and the aqueous phase was extracted with CH2Cl2 (3 x 50mL). The crude mixture was purified using gradient column chromatography (CH2Cl2/MeOH/AcOH from 96.5percent/3percent/0.5percent --> 93.5percent/6percent/0.5percent) and lyophilized from dioxane, resulting in a colorless oil (1.94 g, 89percent). In accordance with literature:24 1H-NMR (400 MHz, CDCl3) δ:7.76 (d, J = 7.5 Hz, 2H), 7.59 (d, J= 6.9 Hz, 2H), 7.40 (t, J= 7.5 Hz, 2H), 7.31 (t, J= 7.5 Hz, 2H), 5.34 (d, J = 7.8 Hz, 1H), 4.54 (br s, 1H), 4.43 (d, J = 6.6 Hz, 2H), 4.22 (t, J = 6.6 Hz, 1H), 3.27 (t, J= 6.6 Hz, 2H), 1.3-2.0 (m, 2H). HRMS (ESI+) m/zcalcd for C2,H23N4O8[M+H]+ 395.1719, found 395.1718.
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 5, p. 1117 - 1129
[2] Chemical Communications, 2011, vol. 47, # 9, p. 2589 - 2591
[3] Chemical Communications, 2018, vol. 54, # 23, p. 2846 - 2849
[4] Patent: EP2532639, 2012, A1, . Location in patent: Page/Page column 5; 6
[5] Angewandte Chemie, International Edition, 2015, vol. 54, # 19, p. 5784 - 5788[6] Angewandte Chemie, 2015, vol. 127, # 19, p. 5876 - 5880,5
[7] Chemical Communications, 2015, vol. 51, # 67, p. 13221 - 13224
[8] Synlett, 2012, vol. 23, # 18, p. 2643 - 2646,4
[9] Synlett, 2012, vol. 23, # 18, p. 2643 - 2646
[10] Chemistry - A European Journal, 2016, vol. 22, # 51, p. 18419 - 18428
[11] Organic and Biomolecular Chemistry, 2017, vol. 15, # 26, p. 5602 - 5608
[12] Amino Acids, 2014, vol. 46, # 4, p. 1033 - 1046
[13] Angewandte Chemie - International Edition, 2016, vol. 55, # 33, p. 9562 - 9566[14] Angew. Chem., 2016, vol. 128, p. 9714 - 9718,5
[15] Journal of the American Chemical Society, 2016, vol. 138, # 18, p. 5773 - 5776
[16] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 14, p. 3752 - 3755
[17] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 23, p. 8350 - 8355
[18] Organic Letters, 2007, vol. 9, # 1, p. 1 - 4
[19] Australian Journal of Chemistry, 2010, vol. 63, # 8, p. 1169 - 1172
[20] Journal of the American Chemical Society, 2012, vol. 134, # 32, p. 13208 - 13211
[21] European Journal of Organic Chemistry, 2013, # 22, p. 4933 - 4943
[22] Tetrahedron Letters, 2014, vol. 55, # 3, p. 606 - 609
[23] ChemMedChem, 2015, vol. 10, # 9, p. 1564 - 1569
  • 11
  • [ 105047-45-8 ]
  • [ 159610-89-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 8, p. 1901 - 1904
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 105047-45-8 ]

Amino Acid Derivatives

Chemical Structure| 144701-24-6

[ 144701-24-6 ]

Fmoc-D-Nva-OH

Similarity: 1.00

Chemical Structure| 121343-82-6

[ 121343-82-6 ]

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)pentanedioic acid

Similarity: 1.00

Chemical Structure| 104091-09-0

[ 104091-09-0 ]

Fmoc-D-Glu-OH

Similarity: 1.00

Chemical Structure| 1262886-65-6

[ 1262886-65-6 ]

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)nonanoic acid

Similarity: 1.00

Chemical Structure| 135112-28-6

[ 135112-28-6 ]

Fmoc-Nva-OH

Similarity: 1.00