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[ CAS No. 4668-42-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 4668-42-2
Chemical Structure| 4668-42-2
Structure of 4668-42-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4668-42-2 ]

CAS No. :4668-42-2 MDL No. :MFCD00083277
Formula : C13H15NO6 Boiling Point : -
Linear Structure Formula :- InChI Key :MFFFBNAPQRDRQW-JTQLQIEISA-N
M.W : 281.26 Pubchem ID :7021783
Synonyms :
Z-Asp-OMe

Calculated chemistry of [ 4668-42-2 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.31
Num. rotatable bonds : 9
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 67.78
TPSA : 101.93 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.42
Log Po/w (XLOGP3) : 0.89
Log Po/w (WLOGP) : 0.78
Log Po/w (MLOGP) : 0.82
Log Po/w (SILICOS-IT) : 0.7
Consensus Log Po/w : 0.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.77
Solubility : 4.75 mg/ml ; 0.0169 mol/l
Class : Very soluble
Log S (Ali) : -2.62
Solubility : 0.682 mg/ml ; 0.00243 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.44
Solubility : 1.01 mg/ml ; 0.0036 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.05

Safety of [ 4668-42-2 ]

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

Application In Synthesis of [ 4668-42-2 ]

* 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 [ 4668-42-2 ]
  • Downstream synthetic route of [ 4668-42-2 ]

[ 4668-42-2 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 67-56-1 ]
  • [ 57933-83-2 ]
  • [ 1152-61-0 ]
  • [ 3160-47-2 ]
  • [ 4668-42-2 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
[2] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
  • 2
  • [ 1152-61-0 ]
  • [ 79-22-1 ]
  • [ 3160-47-2 ]
  • [ 4668-42-2 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
  • 3
  • [ 67-56-1 ]
  • [ 1152-61-0 ]
  • [ 79-22-1 ]
  • [ 3160-47-2 ]
  • [ 4668-42-2 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
  • 4
  • [ 67-56-1 ]
  • [ 4515-23-5 ]
  • [ 3160-47-2 ]
  • [ 4668-42-2 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
[2] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
  • 5
  • [ 4668-42-2 ]
  • [ 17812-32-7 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1973, vol. 46, p. 3187 - 3193
  • 6
  • [ 4668-42-2 ]
  • [ 5545-52-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1964, vol. 94, p. 695 - 709
  • 7
  • [ 67-56-1 ]
  • [ 4515-23-5 ]
  • [ 4668-42-2 ]
YieldReaction ConditionsOperation in experiment
54%
Stage #1: at 20℃; for 5 h;
Stage #2: With N-cyclohexyl-cyclohexanamine In di-isopropyl ether
Stage #3: With hydrogenchloride In water; ethyl acetate
49.0 g (196 mmol) of (S)-benzyl(2,5-dioxotetrahydrofuran-3-yl)carbamate obtained in Step 1-1(2) was dissolved in 100 mL of ethyl acetate, and then 150 mL of methanol was added thereto, followed by stirring at room temperature for 5 hours. The mixture was dried under vacuum and dissolved in 200 mL of diisopropylether, and 34 mL of dicyclohexylamine was slowly added dropwise under stirring. The produced salt of (S)-3-((benzyloxycarbonyl)amino)-4-methoxy-4-oxobutanoic acid dicyclohexylamine was filtered, and suspended in 200 mL of distilled water. 200 mL of ethyl acetate was added thereto, and was adjusted to pH 2 with 6 N hydrochloric acid. After phase-separation, the organic layer was washed several times with distilled water, and dried over magnesium sulfate, followed by concentration under reduced pressure. 200 mL of diethyl ether and 20 mL of petroleum ether were added to the residual concentrate for crystallization. The produced crystals were filtered to give 32.3 g of the title compound (yield: 54percent). 1H NMR(300MHz, CDCl3)δ7.37(m, 5H), 5.76(d, 1H), 5.13(s, 1H), 4.65(m, 1H), 3.76(s, 2H), 3.00(dd, 2H)
Reference: [1] Patent: WO2012/148246, 2012, A2, . Location in patent: Page/Page column 13
  • 8
  • [ 4668-37-5 ]
  • [ 4668-42-2 ]
Reference: [1] Chemical Communications, 1996, # 3, p. 349 - 350
[2] Organic Letters, 2013, vol. 15, # 3, p. 448 - 451
[3] Chemistry - A European Journal, 2015, vol. 21, # 32, p. 11340 - 11343
[4] Recueil des Travaux Chimiques des Pays-Bas, 1965, vol. 84, p. 1315 - 1318
[5] Tetrahedron Letters, 2003, vol. 44, # 28, p. 5251 - 5253
  • 9
  • [ 67-56-1 ]
  • [ 1152-61-0 ]
  • [ 4668-42-2 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 23, p. 2719 - 2721
[2] Hoppe-Seyler's Zeitschrift für physiologische Chemie, 1963, vol. 333, p. 108 - 113
  • 10
  • [ 67-56-1 ]
  • [ 57933-83-2 ]
  • [ 1152-61-0 ]
  • [ 3160-47-2 ]
  • [ 4668-42-2 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
[2] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
  • 11
  • [ 1152-61-0 ]
  • [ 79-22-1 ]
  • [ 3160-47-2 ]
  • [ 4668-42-2 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
  • 12
  • [ 124-41-4 ]
  • [ 23632-66-8 ]
  • [ 35909-93-4 ]
  • [ 1428260-93-8 ]
  • [ 4668-42-2 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 15, p. 1987 - 1990
  • 13
  • [ 63327-57-1 ]
  • [ 4668-42-2 ]
Reference: [1] Synthetic Communications, 1992, vol. 22, # 6, p. 883 - 891
  • 14
  • [ 67-56-1 ]
  • [ 1152-61-0 ]
  • [ 79-22-1 ]
  • [ 3160-47-2 ]
  • [ 4668-42-2 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
  • 15
  • [ 35909-92-3 ]
  • [ 4668-42-2 ]
Reference: [1] Journal of the Indian Chemical Society, 1998, vol. 75, # 10-12, p. 583 - 589
  • 16
  • [ 2304-96-3 ]
  • [ 4668-42-2 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 28, p. 5251 - 5253
[2] Organic Letters, 2013, vol. 15, # 3, p. 448 - 451
[3] Chemistry - A European Journal, 2015, vol. 21, # 32, p. 11340 - 11343
  • 17
  • [ 15545-10-5 ]
  • [ 4668-42-2 ]
  • [ 137816-71-8 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 40, p. 5615 - 5618
  • 18
  • [ 2717-76-2 ]
  • [ 4668-42-2 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1987, # 14, p. 1085 - 1086
  • 19
  • [ 67-56-1 ]
  • [ 4515-23-5 ]
  • [ 3160-47-2 ]
  • [ 4668-42-2 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
[2] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
  • 20
  • [ 501-53-1 ]
  • [ 4668-42-2 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 28, p. 5251 - 5253
[2] Patent: WO2012/148246, 2012, A2,
[3] Chemistry - A European Journal, 2015, vol. 21, # 32, p. 11340 - 11343
  • 21
  • [ 1152-61-0 ]
  • [ 4668-42-2 ]
Reference: [1] Patent: WO2012/148246, 2012, A2,
[2] Tetrahedron Letters, 2013, vol. 54, # 15, p. 1987 - 1990
  • 22
  • [ 5545-52-8 ]
  • [ 4668-42-2 ]
Reference: [1] Synthetic Communications, 1992, vol. 22, # 6, p. 883 - 891
  • 23
  • [ 41446-22-4 ]
  • [ 4668-42-2 ]
Reference: [1] Synthetic Communications, 1992, vol. 22, # 6, p. 883 - 891
  • 24
  • [ 67-56-1 ]
  • [ 88966-25-0 ]
  • [ 4668-42-2 ]
Reference: [1] Gazzetta Chimica Italiana, 1964, vol. 94, p. 695 - 709
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