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[ CAS No. 7536-58-5 ] {[proInfo.proName]}

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Chemical Structure| 7536-58-5
Chemical Structure| 7536-58-5
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Product Details of [ 7536-58-5 ]

CAS No. :7536-58-5 MDL No. :MFCD00065564
Formula : C16H21NO6 Boiling Point : -
Linear Structure Formula :- InChI Key :SOHLZANWVLCPHK-LBPRGKRZSA-N
M.W : 323.34 Pubchem ID :1581888
Synonyms :
(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid;Boc-L-Asp(OBn)-OH

Calculated chemistry of [ 7536-58-5 ]

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.44
Num. rotatable bonds : 10
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 82.24
TPSA : 101.93 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.19
Log Po/w (XLOGP3) : 1.88
Log Po/w (WLOGP) : 1.95
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 1.58
Consensus Log Po/w : 1.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.56
Solubility : 0.886 mg/ml ; 0.00274 mol/l
Class : Soluble
Log S (Ali) : -3.64
Solubility : 0.0736 mg/ml ; 0.000228 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.25
Solubility : 0.183 mg/ml ; 0.000566 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.32

Safety of [ 7536-58-5 ]

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 [ 7536-58-5 ]

* 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 [ 7536-58-5 ]
  • Downstream synthetic route of [ 7536-58-5 ]

[ 7536-58-5 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 7536-58-5 ]
  • [ 13726-67-5 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 2, p. 311 - 313
[2] Organic and Biomolecular Chemistry, 2011, vol. 9, # 8, p. 2597 - 2601
[3] Journal of Organic Chemistry, 1979, vol. 44, p. 3442 - 3444
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 5, p. 1064 - 1067
[5] Tetrahedron Letters, 2007, vol. 48, # 46, p. 8230 - 8233
[6] Tetrahedron Letters, 1993, vol. 34, # 44, p. 7031 - 7034
  • 2
  • [ 7536-58-5 ]
  • [ 2177-63-1 ]
Reference: [1] Journal of the American Chemical Society, 1995, vol. 117, # 17, p. 4729 - 4741
[2] Tetrahedron, 2016, vol. 72, # 13, p. 1706 - 1715
  • 3
  • [ 24424-99-5 ]
  • [ 2177-63-1 ]
  • [ 7536-58-5 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydrogencarbonate In tetrahydrofuran at 0 - 20℃; for 12.5 h; In the single-port in round bottomed flask add L - aspartic acid -4 - benzyl ester (79.7g, 357mmol), sodium bicarbonate (60g, 714.2mmol), water (700 ml) and tetrahydrofuran (550 ml). The reaction system is cooled to 0 °C, the reaction bottle adds by drops two carbon acid tert-butyl ester in (105g, 481mmol), the completion of the dropping, 0 °C reaction under half an hour later, slowly increased to room temperature, stirring for 12 hours. Reduced pressure to remove tetrahydrofuran, aqueous phase of ethyl acetate (20 ml) washing. The aqueous phase is 10percent of the aqueous solution of citric acid (10 ml) to adjust the pH to 1, ethyl acetate (200 ml × 2) extraction, the combined organic phase, the organic phase with saturated salt water (100 ml × 2) washing, drying with anhydrous sodium sulfate. Filtering, evaporating the solvent under reduced pressure, to obtain white solid (104g, 90percent).
56% With sodium hydroxide In tetrahydrofuran; water; acetonitrile for 24.5 h; Cooling L-Aspartic acid b-benzyl ester (5) (3 g, 13.4 mmol) was dissolved in 1 M sodium hydroxide (13 mL) and tetrahydrofuran-acetonitrile (1:1 (v/v), 26 mL). To the cooled solution was added dropwise an acetonitrile solution containing di-t-butyloxy-dicarbonate (3.22 g, 14.7 mmol) over 0.5 h. The solution was adjusted to pH 8 by adding 1 M sodium hydroxide (5 mL). The reaction solution was stirred for 24 h and evaporated in vacuo to give an oily product. The cooled oil was acidified with 10 percent potassium hydrogen sulfate (30 mL) to pH 2 and the resulting solution was extracted with ethyl acetate (30 mL × 3). The extracts were combined and dried with anhydrous magnesium sulfate and the evaporation of the filtrate gave a precipitate. Twice recrystallization with ethyl acetate petroleum ether gave 2.5 g (56 percent). m.p. 98 °C (lit.24) 99 °C).
Reference: [1] Patent: CN106866502, 2017, A, . Location in patent: Paragraph 0230-0234
[2] Organic Syntheses, 1985, vol. 63, p. 160 - 160
[3] Tetrahedron Letters, 1991, vol. 32, # 45, p. 6637 - 6640
[4] Asian Journal of Chemistry, 2014, vol. 26, # 19, p. 6541 - 6548
[5] Journal of the American Chemical Society, 2004, vol. 126, # 42, p. 13612 - 13613
[6] Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 4, p. 235 - 241
[7] Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 4, p. 250 - 256
[8] Doklady Chemistry, 2006, vol. 408, # 1, p. 57 - 60
[9] Journal of Medicinal Chemistry, 2006, vol. 49, # 20, p. 5932 - 5938
[10] Heterocycles, 2008, vol. 76, # 2, p. 1593 - 1606
[11] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 12, p. 3220 - 3224
[12] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 7, p. 2133 - 2140
[13] Chemical Communications, 2017, vol. 53, # 37, p. 5155 - 5158
  • 4
  • [ 13726-67-5 ]
  • [ 100-51-6 ]
  • [ 7536-58-5 ]
Reference: [1] Tetrahedron, 2016, vol. 72, # 13, p. 1706 - 1715
  • 5
  • [ 149636-02-2 ]
  • [ 7536-58-5 ]
Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 17, p. 2783 - 2786
[2] Organic Letters, 2005, vol. 7, # 9, p. 1723 - 1724
  • 6
  • [ 24424-99-5 ]
  • [ 7536-58-5 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 9, p. 2369 - 2376
  • 7
  • [ 130052-03-8 ]
  • [ 7536-58-5 ]
Reference: [1] Chemistry of Natural Compounds, 1990, vol. 26, # 2, p. 196 - 198[2] Khimiya Prirodnykh Soedinenii, 1990, # 2, p. 241 - 245
  • 8
  • [ 1361400-95-4 ]
  • [ 7536-58-5 ]
Reference: [1] Synlett, 2012, # 1, p. 142 - 144
  • 9
  • [ 2886-33-1 ]
  • [ 7536-58-5 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 9, p. 2369 - 2376
  • 10
  • [ 30750-74-4 ]
  • [ 7536-58-5 ]
Reference: [1] Chemistry of Natural Compounds, 1990, vol. 26, # 2, p. 196 - 198[2] Khimiya Prirodnykh Soedinenii, 1990, # 2, p. 241 - 245
[3] Chemistry of Natural Compounds, 1990, vol. 26, # 2, p. 196 - 198[4] Khimiya Prirodnykh Soedinenii, 1990, # 2, p. 241 - 245
  • 11
  • [ 130052-01-6 ]
  • [ 7536-58-5 ]
Reference: [1] Chemistry of Natural Compounds, 1990, vol. 26, # 2, p. 196 - 198[2] Khimiya Prirodnykh Soedinenii, 1990, # 2, p. 241 - 245
[3] Chemistry of Natural Compounds, 1990, vol. 26, # 2, p. 196 - 198[4] Khimiya Prirodnykh Soedinenii, 1990, # 2, p. 241 - 245
  • 12
  • [ 18942-25-1 ]
  • [ 7536-58-5 ]
Reference: [1] Chemical and pharmaceutical bulletin, 1967, vol. 15, # 12, p. 2015 - 2016
  • 13
  • [ 100-39-0 ]
  • [ 7536-58-5 ]
Reference: [1] Chemistry of Natural Compounds, 1990, vol. 26, # 2, p. 196 - 198[2] Khimiya Prirodnykh Soedinenii, 1990, # 2, p. 241 - 245
  • 14
  • [ 100-51-6 ]
  • [ 7536-58-5 ]
Reference: [1] Asian Journal of Chemistry, 2014, vol. 26, # 19, p. 6541 - 6548
  • 15
  • [ 18595-34-1 ]
  • [ 2177-63-1 ]
  • [ 7536-58-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1968, vol. 716, p. 175 - 185
  • 16
  • [ 1070-19-5 ]
  • [ 2177-63-1 ]
  • [ 7536-58-5 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1975, p. 2543 - 2546
  • 17
  • [ 7536-58-5 ]
  • [ 6327-59-9 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 9, p. 2369 - 2376
  • 18
  • [ 7536-58-5 ]
  • [ 65710-57-8 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 2, p. 213 - 215
  • 19
  • [ 7536-58-5 ]
  • [ 81323-58-2 ]
Reference: [1] Tetrahedron, 2001, vol. 57, # 30, p. 6557 - 6566
[2] Patent: WO2011/20018, 2011, A1,
[3] Journal of the American Chemical Society, 2011, vol. 133, # 4, p. 1122 - 1133
[4] Molecular Pharmaceutics, 2014, vol. 11, # 11, p. 3852 - 3866
  • 20
  • [ 7536-58-5 ]
  • [ 34582-32-6 ]
Reference: [1] Tetrahedron, 2001, vol. 57, # 30, p. 6557 - 6566
[2] Journal of Organic Chemistry, 1993, vol. 58, # 9, p. 2369 - 2376
[3] Patent: WO2011/20018, 2011, A1,
[4] Journal of the American Chemical Society, 2011, vol. 133, # 4, p. 1122 - 1133
[5] Molecular Pharmaceutics, 2014, vol. 11, # 11, p. 3852 - 3866
  • 21
  • [ 7536-58-5 ]
  • [ 104227-71-6 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 19, p. 3489 - 3492
  • 22
  • [ 7536-58-5 ]
  • [ 83345-44-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 7, p. 2133 - 2140
  • 23
  • [ 7536-58-5 ]
  • [ 541-41-3 ]
  • [ 83345-44-2 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 19, p. 3489 - 3492
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