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[ CAS No. 405-39-0 ] {[proInfo.proName]}

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Chemical Structure| 405-39-0
Chemical Structure| 405-39-0
Structure of 405-39-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 405-39-0 ]

CAS No. :405-39-0 MDL No. :MFCD00037822
Formula : C22H26N2O6 Boiling Point : -
Linear Structure Formula :- InChI Key :BLZXFNUZFTZCFD-IBGZPJMESA-N
M.W : 414.45 Pubchem ID :7269422
Synonyms :

Calculated chemistry of [ 405-39-0 ]

Physicochemical Properties

Num. heavy atoms : 30
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.32
Num. rotatable bonds : 15
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 109.88
TPSA : 113.96 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.72
Log Po/w (XLOGP3) : 3.35
Log Po/w (WLOGP) : 3.16
Log Po/w (MLOGP) : 2.35
Log Po/w (SILICOS-IT) : 2.74
Consensus Log Po/w : 2.86

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.83
Solubility : 0.0619 mg/ml ; 0.000149 mol/l
Class : Soluble
Log S (Ali) : -5.42
Solubility : 0.00157 mg/ml ; 0.0000038 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.16
Solubility : 0.000289 mg/ml ; 0.000000698 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.48

Safety of [ 405-39-0 ]

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 [ 405-39-0 ]

* 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 [ 405-39-0 ]
  • Downstream synthetic route of [ 405-39-0 ]

[ 405-39-0 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 6066-82-6 ]
  • [ 405-39-0 ]
  • [ 21160-83-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 9, p. 1658 - 1663
[2] Journal of Organic Chemistry, 1995, vol. 60, # 7, p. 1932 - 1935
[3] Journal of Organic Chemistry, 1986, vol. 51, # 17, p. 3320 - 3324
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 8, p. 2518 - 2526
[5] Synlett, 2005, # 18, p. 2802 - 2804
[6] Patent: WO2014/194030, 2014, A2, . Location in patent: Paragraph 245
  • 2
  • [ 56-87-1 ]
  • [ 501-53-1 ]
  • [ 405-39-0 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydroxide In 1,4-dioxane; water at 20℃; for 1 h; This synthesis is in accordance with Galbiati, B.; Ferrario, T.; Merli, V. WP 0110851(2001). A 250 mL three-necked flask was loaded consecutively with water (20 mL), 1,4-dioxane (20 mL) and L-lysine (2.1 g, 14.4 mmol). The mixture was stirred until complete dissolution. The pH was adjusted to about 10.5 by addition of 30percent NaOH. Benzylchloroformate (5.2 g, 30.6 mmol) was added while maintaining the pH at about 1011 by adding at the same time 30percent NaOH. At the end of the addition, the reaction was stirred at 20° C. for about 1 hour. The pH was adjusted to 5 with 37percent HCl. Ethyl acetate (30 mL) was added and the pH was adjusted to 1 with 37percent HCl. The mixture was stirred at room temperature for about 30 minutes, the organic layer was separated and the aqueous layer was extracted with ethyl acetate (20 mL). The combined organic layer was washed with brine (30 mL), and dried over Na2SO4. Then, the solvent was evaporated to yield a yellowish oil (6.0 g, 99percent). The oil was pre-dried by azeotropic distillation with benzene.
95% With sodium carbonate In diethyl ether; water at 0℃; for 5 h; 1. 155 mol of Cbz-Cl was dissolved in 100 mL of diethyl ether solution,200 mL of a 10percent NaCO3 aqueous solution containing 0.0645 mol of L-lysine was added dropwise,After the addition was completed, the reaction was maintained at 0 ° C for 5 hours, and the product was obtained with an appropriate amount of 10percent lemonAcidified and extracted with chloroform,The reaction layer was washed with water to give a large amount of waterN, N'-bis-benzyloxycarbonyl-L-lysine,The yield is about 95percent.
93% With sodium carbonate In diethyl ether; water at 0℃; for 5 h; Step 1, 0.322 mol of Cbz-Cl was dissolved in 100 mL of diethyl ether solution,200 mL of a 10percent NaCO3 aqueous solution containing 0.055 mol of L-lysine was added dropwise,After the dropwise addition to maintain the temperature 0 reaction 5h,The resulting product was acidified with an appropriate amount of 10percent citric acid and extracted with trichloromethane.The product was washed with water and evaporated to give a large amount of N, N'-bis-benzyloxycarbonyl-L-lysine,The yield is about 93percent.
Reference: [1] Patent: US2006/94673, 2006, A1, . Location in patent: Page/Page column 4
[2] Patent: CN106565771, 2017, A, . Location in patent: Paragraph 0037; 0038; 0039
[3] Patent: CN106565772, 2017, A, . Location in patent: Paragraph 0038
[4] Helvetica Chimica Acta, 1958, vol. 41, p. 1867,1876
[5] Journal of Biological Chemistry, 1935, vol. 111, p. 245,251
[6] Organic Mass Spectrometry, 1994, vol. 29, # 5, p. 260 - 265
[7] Patent: WO2006/133144, 2006, A2, . Location in patent: Page/Page column 70
  • 3
  • [ 1155-64-2 ]
  • [ 501-53-1 ]
  • [ 405-39-0 ]
YieldReaction ConditionsOperation in experiment
99% With sodium carbonate In 1,4-dioxane; water at 20℃; for 1 h; Preparation of Compound 24e A three-necked flask was loaded consecutively with H2O (40 mL), 1,4-dioxane (70 mL) and H-Lys(Z)-OH (10 g, 35.7 mmol). The mixture was stirred until complete dissolution. The pH was adjusted to about 10.5 by adding of 2 M aqueous Na2CO3. Benzyl chloroformate (6.69 g, 39.2 mmol) was added while maintaining the pH at about 10-11 by adding at the same time 2 M aqueous Na2CO3. After completing addition, the reaction mixture was stirred at 20 °C for 1 hour. Then EtOAc (50 mL) was added and pH of the resulting mixture was adjusted to 2-3 with c-HCl. The organic layer was separated and the aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were washed with brine (50 mL), and dried over Na2SO4. Filtration and concentration under reduced pressure yielded the compound 24e as yellowish oil (14.7g, 99 percent). 1H-NMR (400 MHz, CDC13) δ 7.33-7.27 (m, 10H), 5.07-5.04 (d, 4H), 4.08 (m, 1H), 3.09 (t, 2H), 1.51 (br s, 1H), 1.49 (bs, 1H), 1.47-1.40 (m, 4H).
Reference: [1] Patent: WO2017/89890, 2017, A1, . Location in patent: Page/Page column 117
[2] Chemistry - A European Journal, 2014, vol. 20, # 26, p. 8116 - 8128
[3] Tetrahedron, 2014, vol. 70, # 34, p. 5197 - 5206
  • 4
  • [ 24498-31-5 ]
  • [ 501-53-1 ]
  • [ 405-39-0 ]
YieldReaction ConditionsOperation in experiment
99% With sodium carbonate In 1,4-dioxane; water at 20℃; for 1 h; A three-necked flask was loaded consecutively with H20 (40 mL), 1,4-dioxane (70 mL) and H-Lys(Z)-OH (10 g, 35.7 mmol). The mixture was stirred until complete dissolution. The pH was adjusted to about 10.5 by adding of 2 M aqueous Na2C03. Benzyl chloroformate (6.69 g, 39.2 mmol) was added while maintaining the pH at about 10-11 by adding at the same time 2 M aqueous Na2C03. After completing addition, the reaction mixture was stirred at 20 °C for 1 hour. Then EtOAc (50 mL) was added and pH of the resulting mixture was adjusted to 2-3 with c-HCl. The organic layer was separated and the aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were washed with brine (50 mL), and dried over Na2S04. Filtration and concentration under reduced pressure yielded the compound 24e as yellowish oil (14.7g, 99 percent). 1H-NMR (400 MHz, CDC13) δ 7.33-7.27 (m, 10H), 5.07-5.04 (d, 4H), 4.08 (m, 1H), 3.09 (t, 2H), 1.51 (br s, 1H), 1.49 (bs, 1H), 1.47-1.40 (m, 4H).
Reference: [1] Patent: WO2017/89894, 2017, A1, . Location in patent: Page/Page column 127
  • 5
  • [ 144889-39-4 ]
  • [ 405-39-0 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 37, p. 5441 - 5444
  • 6
  • [ 657-27-2 ]
  • [ 501-53-1 ]
  • [ 405-39-0 ]
Reference: [1] Journal of the American Chemical Society, 1998, vol. 120, # 41, p. 10646 - 10652
  • 7
  • [ 657-27-2 ]
  • [ 405-39-0 ]
  • [ 1155-64-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3103 - 3108
  • 8
  • [ 32279-04-2 ]
  • [ 405-39-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3103 - 3108
  • 9
  • [ 501-53-1 ]
  • [ 405-39-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3103 - 3108
  • 10
  • [ 19506-72-0 ]
  • [ 56-87-1 ]
  • [ 405-39-0 ]
Reference: [1] Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1968, vol. 16, p. 23 - 27
  • 11
  • [ 55592-84-2 ]
  • [ 405-39-0 ]
Reference: [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1934, vol. 224, p. 33,35
  • 12
  • [ 56-87-1 ]
  • [ 63842-04-6 ]
  • [ 405-39-0 ]
Reference: [1] Australian Journal of Chemistry, 1966, vol. 19, p. 1297 - 1298
  • 13
  • [ 56-87-1 ]
  • [ 5335-05-7 ]
  • [ 405-39-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1961, vol. 646, p. 101 - 118
  • 14
  • [ 21160-82-7 ]
  • [ 100-02-7 ]
  • [ 405-39-0 ]
Reference: [1] Gazzetta Chimica Italiana, 1982, vol. 112, # 7/8, p. 307 - 318
  • 15
  • [ 405-39-0 ]
  • [ 27894-50-4 ]
Reference: [1] Helvetica Chimica Acta, 1958, vol. 41, p. 1867,1876
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