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[ CAS No. 71989-20-3 ] {[proInfo.proName]}

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Chemical Structure| 71989-20-3
Chemical Structure| 71989-20-3
Structure of 71989-20-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 71989-20-3 ]

CAS No. :71989-20-3 MDL No. :MFCD00037137
Formula : C20H20N2O5 Boiling Point : -
Linear Structure Formula :C13H9CH2OCONHCH(CH2)2CONH2CO2H InChI Key :IZKGGDFLLNVXNZ-KRWDZBQOSA-N
M.W : 368.38 Pubchem ID :2724775
Synonyms :
Fmoc-L-glutamine

Calculated chemistry of [ 71989-20-3 ]

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.25
Num. rotatable bonds : 9
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 97.69
TPSA : 118.72 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : 1.89
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 1.5
Log Po/w (SILICOS-IT) : 2.04
Consensus Log Po/w : 1.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.05
Solubility : 0.329 mg/ml ; 0.000892 mol/l
Class : Soluble
Log S (Ali) : -4.01
Solubility : 0.0364 mg/ml ; 0.0000987 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.87
Solubility : 0.00496 mg/ml ; 0.0000135 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.84

Safety of [ 71989-20-3 ]

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 [ 71989-20-3 ]

* 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 [ 71989-20-3 ]
  • Downstream synthetic route of [ 71989-20-3 ]

[ 71989-20-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 71989-20-3 ]
  • [ 64-19-7 ]
  • [ 2490-97-3 ]
Reference: [1] Asian Journal of Chemistry, 2014, vol. 26, # 10, p. 2941 - 2944
  • 2
  • [ 76-84-6 ]
  • [ 71989-20-3 ]
  • [ 132327-80-1 ]
Reference: [1] Patent: US5354843, 1994, A,
  • 3
  • [ 56-85-9 ]
  • [ 71989-20-3 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In acetonitrile at 20℃; for 2 h; General procedure: To a solution of H-Phe-OH (100 mg, 60.5 mmol) in 50 percent MeCN (6.1 mL)were added Fmoc-OPhth (233 mg, 60.5 mmol) and K2CO3 (167 mg, 121 mmol) and stirred at room temperature. After 2 h of stirring saturated sodium bicarbonate solution and H2O were added and the resulting solution was washed with diethyl ether. The aqueous phase is acidified to pH 1 with 1M HCl and extracted with diethyl ether. The organic phase was washed with 1 M HCl, H2O, brine, dried over MgSO4. The filtrate was evaporatedevaporated under reduced pressure to give yellow solid as crude product.
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 16, p. 1600 - 1603
  • 4
  • [ 56-85-9 ]
  • [ 82911-69-1 ]
  • [ 71989-20-3 ]
YieldReaction ConditionsOperation in experiment
84% With sodium carbonate In tetrahydrofuran; water To a stirred solution of L-glutamine (1.75 g, 12 mmole) and sodium carbonate (1.27 g, 12 mmole) in 30 ml of water, was added a solution of Fmoc-OSu (3.0 g, 8.9 mmole) in 60 ml of THF. After stirring overnight the mixture was concentrated under reduced pressure to remove the THF. The residue was diluted with 100 ml of 1 N hydrochloric acid . The white solid was collected by filtration and recrystallized in DMF-0.1 N hydrochloric acid aqueous solution to afford a white powder (38, 2.76 g). Yield: 84percent. 1H-NMR (90 MHz, DMSO-d6) ppm: 12.47 (1H, s), 7.89-7.20 (10 H, m), 6.68 (1H, s, br), 4.22-3.90 (4H, m), and 2.25-1.86 (4H, m).
Reference: [1] Journal of Peptide Science, 2017, vol. 23, # 3, p. 202 - 214
[2] Patent: US2006/161007, 2006, A1, . Location in patent: Page/Page column 12
[3] Synthetic Communications, 2009, vol. 39, # 11, p. 2022 - 2031
  • 5
  • [ 56-85-9 ]
  • [ 71989-20-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3103 - 3108
  • 6
  • [ 132327-80-1 ]
  • [ 71989-20-3 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 24, p. 6346 - 6349
  • 7
  • [ 56-85-9 ]
  • [ 88744-04-1 ]
  • [ 71989-20-3 ]
Reference: [1] Synthesis, 1986, # 4, p. 303 - 305
  • 8
  • [ 56-85-9 ]
  • [ 28920-44-7 ]
  • [ 71989-20-3 ]
Reference: [1] Organic Process Research and Development, 2004, vol. 8, # 6, p. 920 - 924
  • 9
  • [ 38756-25-1 ]
  • [ 28920-43-6 ]
  • [ 71989-20-3 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10575 - 10582
  • 10
  • [ 28920-43-6 ]
  • [ 71989-20-3 ]
Reference: [1] Organic Process Research and Development, 2004, vol. 8, # 6, p. 920 - 924
  • 11
  • [ 56-85-9 ]
  • [ 28920-43-6 ]
  • [ 71989-20-3 ]
Reference: [1] Journal of the Chinese Chemical Society, 2011, vol. 58, # 4, p. 509 - 515
  • 12
  • [ 71989-20-3 ]
  • [ 161420-87-7 ]
YieldReaction ConditionsOperation in experiment
86.5% With [bis(acetoxy)iodo]benzene In water; ethyl acetate; acetonitrile at 20 - 30℃; for 72 h; A. The suspension 100g271 . 5nmolFmoc-Gln-OH with 2L ethyl acetate: acetonitrile: water = 2:1: mixed solution 1(v/v/v), in 20-30 °C add 105.1g325 . 9nmolDipa, reaction 72 hours, post-processed to obtain product Fmoc-Dab-OH80g. Yield of 86.5percent, HPLC: 99.6percent. The infrared, nuclear magnetic resonance confirmed correct structure, see Figure 1, Figure 2.
Reference: [1] Bulletin of the Chemical Society of Japan, 2004, vol. 77, # 10, p. 1915 - 1924
[2] Patent: CN105348147, 2016, A, . Location in patent: Paragraph 0014
[3] Synlett, 2011, # 13, p. 1917 - 1919
[4] Journal of Peptide Science, 2017, vol. 23, # 3, p. 202 - 214
[5] European Journal of Medicinal Chemistry, 1995, vol. 30, # 2, p. 115 - 122
[6] Angewandte Chemie - International Edition, 2017, vol. 56, # 2, p. 524 - 529[7] Angew. Chem., 2017, vol. 129, # 2, p. 539 - 544,6
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