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[ CAS No. 40856-59-5 ] {[proInfo.proName]}

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Chemical Structure| 40856-59-5
Chemical Structure| 40856-59-5
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Product Details of [ 40856-59-5 ]

CAS No. :40856-59-5 MDL No. :MFCD04973958
Formula : C9H15NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :IMWMFJMYEKHYKG-LURJTMIESA-N
M.W : 201.22 Pubchem ID :688318
Synonyms :

Calculated chemistry of [ 40856-59-5 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.06
TPSA : 64.63 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) : -6.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 1.02
Log Po/w (WLOGP) : 0.83
Log Po/w (MLOGP) : 0.43
Log Po/w (SILICOS-IT) : 0.59
Consensus Log Po/w : 0.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.47
Solubility : 6.88 mg/ml ; 0.0342 mol/l
Class : Very soluble
Log S (Ali) : -1.97
Solubility : 2.17 mg/ml ; 0.0108 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.34
Solubility : 9.09 mg/ml ; 0.0452 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.85

Safety of [ 40856-59-5 ]

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

Application In Synthesis of [ 40856-59-5 ]

* 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 [ 40856-59-5 ]
  • Downstream synthetic route of [ 40856-59-5 ]

[ 40856-59-5 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 40856-59-5 ]
  • [ 41088-86-2 ]
Reference: [1] Synthesis (Germany), 2013, vol. 45, # 10, p. 1364 - 1372
  • 2
  • [ 41088-86-2 ]
  • [ 40856-59-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 44, p. 13041 - 13044[2] Angew. Chem., 2015,
[3] Journal of Organic Chemistry, 1986, vol. 51, # 26, p. 5047 - 5050
[4] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4369 - 4378
[5] Tetrahedron Letters, 2000, vol. 41, # 8, p. 1141 - 1145
  • 3
  • [ 24424-99-5 ]
  • [ 6305-38-0 ]
  • [ 40856-59-5 ]
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 15, p. 4121 - 4143
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 19, p. 4755 - 4765
  • 4
  • [ 24424-99-5 ]
  • [ 2185-03-7 ]
  • [ 40856-59-5 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 8, p. 2527 - 2534
[2] Patent: US6297239, 2001, B1,
[3] Patent: US6335343, 2002, B1, . Location in patent: Page column 47
[4] Tetrahedron Asymmetry, 2017, vol. 28, # 9, p. 1163 - 1168
  • 5
  • [ 120042-11-7 ]
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Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 3, p. 988 - 996
  • 6
  • [ 91240-51-6 ]
  • [ 40856-59-5 ]
  • [ 104227-71-6 ]
Reference: [1] Patent: WO2015/63001, 2015, A1, . Location in patent: Page/Page column 19
  • 7
  • [ 24424-99-5 ]
  • [ 40856-59-5 ]
YieldReaction ConditionsOperation in experiment
397 mg
Stage #1: With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 6.5 h;
Stage #2: With toluene-4-sulfonic acid In dichloromethane at 20℃; for 48 h;
To a cold (0°C) solution of (S)-4-Hydroxy-1-methoxy-1-oxobutan-2-aminium chloride (3.5 gm, 21 mmol), suspended in dichloromethane (42 mL) added (Boc)2O(5.06 gm, 23.19 mmol) followed by addition of DIPEA (7.35 mL, 42.17 mmol). The reaction mixture was stirred at 0°C for 30 min and then allowed to stir for 6 hr at room temperature. Purification by silica gel flash column chromatography (EtOAc : Hexane – 1 : 4) yielded the desired product as a mixture of Methyl (tert-butoxycarbonyl)-L-homoserinate and (S)-tert-Butyl(2-oxotetrahydrofuran-3-yl)carbamate (4 gm, 17.13 mmol, 81percent) (TLC: EtOAc– Rf= 0.6, 0.56). Lactone was synthesized by treating the mixture of Methyl (tert-butoxycarbonyl)-L-homoserinate and (S)-tert-Butyl (2-oxotetrahydrofuran-3-yl)carbamate (12) (500 mg, 2.15 mmol) with p-TsOH (123 mg, 0.642 mmol) in dry DCM (35 mL) at room temperature for 48 hrs.Purification by silica gel flash column chromatography (EtOAc : Hexane – 1 : 4)yielded the desired product as a white solid(397 mg, 1.98 mmol, 92percent) (TLC: EtOAc– Rf = 0.6). IR (NaCl,neat): 3365, 2980, 2935, 1778, 1687, 1531, 1456, 1369, 1295, 1269, 1253, 1221,1163, 1107, 1066, 1016, 1001, 979, 950 cm-1; IR (NaCl, 10 mM in CHCl3): 3464, 3433,3026, 3010, 2982, 2934, 2917, 2884, 1785, 1715, 1504, 1371, 1292, 1218, 1161,1081, 864, 783, 703 cm-1; H NMR (400 MHz, CDCl3) δ ppm: 5.04 (bs,1H), 4.45 (t, J = 9.2 Hz, 1H), 4.34(bs, 1H), 4.28-4.21 (m, 1H), 2.79-2.72 (m, 1H), 2.24-2.13 (m, 1H), 1.46 (s,9H); C NMR (100 MHz, CDCl3) δ ppm: 175.4, 155.4, 80.4, 65.7, 50.0, 30.3, 28.2; HRMS m/zCalcd for C9H15NO4Na 224.0899, Found 224.0896.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 42, p. 5771 - 5775
  • 8
  • [ 24424-99-5 ]
  • [ 40856-59-5 ]
  • [ 120042-11-7 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 42, p. 5771 - 5775
  • 9
  • [ 224192-24-9 ]
  • [ 40856-59-5 ]
Reference: [1] European Journal of Organic Chemistry, 2007, # 30, p. 5050 - 5058
  • 10
  • [ 128427-10-1 ]
  • [ 40856-59-5 ]
  • [ 104227-71-6 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 11, p. 3767 - 3770
[2] Journal of the American Chemical Society, 2015, vol. 137, # 11, p. 3767 - 3770
  • 11
  • [ 24424-99-5 ]
  • [ 77856-40-7 ]
  • [ 40856-59-5 ]
Reference: [1] Synthesis, 1996, # 1, p. 39 - 41
  • 12
  • [ 34619-03-9 ]
  • [ 2185-02-6 ]
  • [ 40856-59-5 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 1, p. 385 - 387
  • 13
  • [ 24424-99-5 ]
  • [ 40856-59-5 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 26, p. 5047 - 5050
[2] Synthesis, 1991, # 7, p. 526 - 528
[3] Tetrahedron Letters, 1987, vol. 28, # 31, p. 3605 - 3608
  • 14
  • [ 63-68-3 ]
  • [ 24424-99-5 ]
  • [ 40856-59-5 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 8, p. 3212 - 3217
  • 15
  • [ 24424-99-5 ]
  • [ 2185-02-6 ]
  • [ 40856-59-5 ]
Reference: [1] Synthesis (Germany), 2013, vol. 45, # 10, p. 1364 - 1372
  • 16
  • [ 24424-99-5 ]
  • [ 40856-59-5 ]
  • [ 104227-71-6 ]
Reference: [1] Patent: WO2015/63001, 2015, A1,
  • 17
  • [ 66543-86-0 ]
  • [ 40856-59-5 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 31, p. 3605 - 3608
  • 18
  • [ 135941-84-3 ]
  • [ 40856-59-5 ]
Reference: [1] Synthesis, 1991, # 7, p. 526 - 528
  • 19
  • [ 91240-51-6 ]
  • [ 40856-59-5 ]
  • [ 104227-71-6 ]
Reference: [1] Patent: WO2015/63001, 2015, A1, . Location in patent: Page/Page column 19
  • 20
  • [ 128427-10-1 ]
  • [ 40856-59-5 ]
  • [ 104227-71-6 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 11, p. 3767 - 3770
[2] Journal of the American Chemical Society, 2015, vol. 137, # 11, p. 3767 - 3770
  • 21
  • [ 24424-99-5 ]
  • [ 40856-59-5 ]
  • [ 104227-71-6 ]
Reference: [1] Patent: WO2015/63001, 2015, A1,
  • 22
  • [ 24424-99-5 ]
  • [ 40856-59-5 ]
  • [ 120042-11-7 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 42, p. 5771 - 5775
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