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[ CAS No. 71989-26-9 ] {[proInfo.proName]}

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Chemical Structure| 71989-26-9
Chemical Structure| 71989-26-9
Structure of 71989-26-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 71989-26-9 ]

CAS No. :71989-26-9 MDL No. :MFCD00037138
Formula : C26H32N2O6 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :468.54 Pubchem ID :-
Synonyms :
Fmoc-L-Lys (Boc)-OH

Calculated chemistry of [ 71989-26-9 ]

Physicochemical Properties

Num. heavy atoms : 34
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.42
Num. rotatable bonds : 14
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 128.14
TPSA : 113.96 Ų

Pharmacokinetics

GI absorption : High
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) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.06
Log Po/w (XLOGP3) : 4.46
Log Po/w (WLOGP) : 4.67
Log Po/w (MLOGP) : 2.8
Log Po/w (SILICOS-IT) : 3.8
Consensus Log Po/w : 3.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.89
Solubility : 0.00601 mg/ml ; 0.0000128 mol/l
Class : Moderately soluble
Log S (Ali) : -6.57
Solubility : 0.000125 mg/ml ; 0.000000268 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -6.95
Solubility : 0.0000526 mg/ml ; 0.000000112 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.51

Safety of [ 71989-26-9 ]

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

Application In Synthesis of [ 71989-26-9 ]

* 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 [ 71989-26-9 ]
  • Downstream synthetic route of [ 71989-26-9 ]

[ 71989-26-9 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 29022-11-5 ]
  • [ 71989-26-9 ]
  • [ 109425-51-6 ]
  • [ 49557-75-7 ]
Reference: [1] Dalton Transactions, 2005, # 4, p. 728 - 734
  • 2
  • [ 108-24-7 ]
  • [ 71989-26-9 ]
  • [ 23500-04-1 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 12, p. 4695 - 4702
  • 3
  • [ 71989-26-9 ]
  • [ 2418-95-3 ]
YieldReaction ConditionsOperation in experiment
95% With piperidine In dichloromethane at 20℃; for 16 h; Step 1. To a stirred solution of compound 20-1 (5 g, 10.7 mmol) in DCM was added compound 20-2 (5.5 ml, 53 mmol) at r.t. The mixture was stirred at r.t. for 16 h. The reaction mixture was extracted with H20 and the combined aqueous layers were concentrated to give 20-3. (Yield: 95 percent)
Reference: [1] Patent: WO2015/95227, 2015, A2, . Location in patent: Page/Page column 103; 104
[2] Organic and Biomolecular Chemistry, 2011, vol. 9, # 4, p. 987 - 993
[3] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 989 - 1000
  • 4
  • [ 71989-26-9 ]
  • [ 4425-82-5 ]
  • [ 2418-95-3 ]
Reference: [1] Chimia, 2010, vol. 64, # 3, p. 200 - 202
  • 5
  • [ 2418-95-3 ]
  • [ 82911-69-1 ]
  • [ 71989-26-9 ]
Reference: [1] Journal of Peptide Science, 2017, vol. 23, # 3, p. 202 - 214
[2] Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 10, p. 1489 - 1490
[3] European Journal of Organic Chemistry, 2015, vol. 2015, # 17, p. 3767 - 3770
[4] Journal of Materials Chemistry B, 2015, vol. 3, # 1, p. 119 - 126
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 2980 - 2983
  • 6
  • [ 82911-69-1 ]
  • [ 71989-26-9 ]
Reference: [1] Patent: US2017/355667, 2017, A1, . Location in patent: Paragraph 0077; 0087
  • 7
  • [ 28920-43-6 ]
  • [ 71989-26-9 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10575 - 10582
  • 8
  • [ 24424-99-5 ]
  • [ 71989-26-9 ]
Reference: [1] Journal of Materials Chemistry B, 2015, vol. 3, # 1, p. 119 - 126
  • 9
  • [ 56-87-1 ]
  • [ 71989-26-9 ]
Reference: [1] Journal of Materials Chemistry B, 2015, vol. 3, # 1, p. 119 - 126
  • 10
  • [ 56-87-1 ]
  • [ 24424-99-5 ]
  • [ 71989-26-9 ]
Reference: [1] Patent: US2017/355667, 2017, A1,
  • 11
  • [ 94142-97-9 ]
  • [ 71989-26-9 ]
  • [ 150629-67-7 ]
YieldReaction ConditionsOperation in experiment
41%
Stage #1: With hydrogenchloride In 1,4-dioxane at 20℃; for 2 h;
Stage #2: With N-ethyl-N,N-diisopropylamine In ethanol for 17 h; Reflux
Fmoc-Lys(Boc)-OH (5.66 g, 12.1 mmol) was dissolved in 4 M HCl/dioxane (120 mL), and stirred at room temperature for 2 h to remove the side-chain Boc group. The solvent was removed under reduced pressure. The resulting residue was dissolved in EtOH(60 mL), and then 2-acetyldimedone (3.36 g, 18.4 mmol) and DIPEA (6.2 mL, 35.6 mmol) were added. The reaction mixture was refluxed for 17 h. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in AcOEt (300 mL) and washed with 1 M HCl (100 mL) and brine (100 mL), dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography(0.5percent–3percent MeOH/DCM) to give Fmoc-Lys(Dde)-OH (2.64 g,41percent) as a white solid. Spectroscopic data are identical to the published data.34 1H NMR (500 MHz, CDCl3): d 13.31 (brs, 1H), 7.75(d, J = 7.8 Hz, 2H), 7.59 (t, J = 7.8 Hz, 2H), 7.38 (t, J = 7.8 Hz, 2H),7.31–7.28 (m, 2H), 5.73 (d, J = 8.0 Hz, 1H), 4.48–4.45 (m, 1H),4.37 (d, J = 7.1 Hz, 2H), 4.20 (t, J = 7.1 Hz, 1H), 3.43–3.40 (m, 2H),2.55 (s, 3H), 2.36 (s, 4H), 2.00–1.50 (m, 6H), 1.01 (s, 6H). HR-MS(m/z, FAB): calcd for C31H37N2O6 ([M + H]+), 533.2652; found,533.2643.
Reference: [1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 3, p. 1227 - 1234
  • 12
  • [ 71989-26-9 ]
  • [ 159766-56-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 47, p. 11167 - 11171
  • 13
  • [ 71989-26-9 ]
  • [ 159610-89-6 ]
Reference: [1] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 80, p. 10007 - 10009,3
[2] Chemical Communications, 2012, vol. 48, # 80, p. 10007 - 10009
[3] Journal of Peptide Science, 2017, vol. 23, # 3, p. 202 - 214
[4] European Journal of Organic Chemistry, 2013, # 22, p. 4933 - 4943
[5] Amino Acids, 2014, vol. 46, # 4, p. 1033 - 1046
[6] European Journal of Organic Chemistry, 2015, vol. 2015, # 5, p. 1117 - 1129
  • 14
  • [ 71989-26-9 ]
  • [ 660847-06-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5582 - 5590
  • 15
  • [ 71989-26-9 ]
  • [ 1026295-98-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5582 - 5590
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