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[ CAS No. 71989-23-6 ] {[proInfo.proName]}

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Chemical Structure| 71989-23-6
Chemical Structure| 71989-23-6
Structure of 71989-23-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 71989-23-6 ]

CAS No. :71989-23-6 MDL No. :MFCD00037125
Formula : C21H23NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :QXVFEIPAZSXRGM-DJJJIMSYSA-N
M.W :353.41 Pubchem ID :2724629
Synonyms :
Fmoc-Ile-OH

Calculated chemistry of [ 71989-23-6 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.33
Num. rotatable bonds : 8
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 99.59
TPSA : 75.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.54
Log Po/w (XLOGP3) : 4.38
Log Po/w (WLOGP) : 4.02
Log Po/w (MLOGP) : 3.0
Log Po/w (SILICOS-IT) : 3.55
Consensus Log Po/w : 3.5

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.6
Solubility : 0.00879 mg/ml ; 0.0000249 mol/l
Class : Moderately soluble
Log S (Ali) : -5.68
Solubility : 0.000731 mg/ml ; 0.00000207 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.71
Solubility : 0.000689 mg/ml ; 0.00000195 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.05

Safety of [ 71989-23-6 ]

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 [ 71989-23-6 ]

* 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 [ 71989-23-6 ]
  • Downstream synthetic route of [ 71989-23-6 ]

[ 71989-23-6 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 35661-60-0 ]
  • [ 71989-23-6 ]
  • [ 36077-41-5 ]
Reference: [1] Marine Drugs, 2013, vol. 11, # 12, p. 4834 - 4857
  • 2
  • [ 29022-11-5 ]
  • [ 35661-60-0 ]
  • [ 1403834-74-1 ]
  • [ 71989-31-6 ]
  • [ 71989-23-6 ]
  • [ 71989-38-3 ]
  • [ 132388-59-1 ]
  • [ 132327-80-1 ]
  • [ 50-56-6 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 3, p. 616 - 619
  • 3
  • [ 29022-11-5 ]
  • [ 35661-60-0 ]
  • [ 71989-31-6 ]
  • [ 71989-23-6 ]
  • [ 71989-38-3 ]
  • [ 103213-32-7 ]
  • [ 132388-59-1 ]
  • [ 132327-80-1 ]
  • [ 50-56-6 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 19, p. 6074 - 6078
  • 4
  • [ 68858-20-8 ]
  • [ 71989-31-6 ]
  • [ 71989-14-5 ]
  • [ 71989-23-6 ]
  • [ 71989-38-3 ]
  • [ 109425-51-6 ]
  • [ 4474-91-3 ]
Reference: [1] European Journal of Inorganic Chemistry, 2016, vol. 2016, # 35, p. 5427 - 5434
  • 5
  • [ 73-32-5 ]
  • [ 71989-23-6 ]
YieldReaction ConditionsOperation in experiment
88% 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
  • 6
  • [ 73-32-5 ]
  • [ 82911-69-1 ]
  • [ 71989-23-6 ]
Reference: [1] Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 5, p. 283 - 287[2] Bioorganicheskaya Khimiya, 1999, vol. 25, # 5, p. 323 - 328
[3] Synthetic Communications, 2009, vol. 39, # 11, p. 2022 - 2031
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 2980 - 2983
  • 7
  • [ 73-32-5 ]
  • [ 28920-43-6 ]
  • [ 71989-23-6 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 24, p. 18751 - 18760
[2] Journal of the Chinese Chemical Society, 2011, vol. 58, # 4, p. 509 - 515
  • 8
  • [ 73-32-5 ]
  • [ 88744-04-1 ]
  • [ 71989-23-6 ]
Reference: [1] Synthesis, 1986, # 4, p. 303 - 305
  • 9
  • [ 73-32-5 ]
  • [ 102774-86-7 ]
  • [ 71989-23-6 ]
Reference: [1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098
  • 10
  • [ 28920-43-6 ]
  • [ 17694-98-3 ]
  • [ 71989-23-6 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10575 - 10582
  • 11
  • [ 71989-23-6 ]
  • [ 133565-46-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 87, p. 46947 - 46950
[2] Tetrahedron Letters, 1991, vol. 32, # 7, p. 923 - 926
[3] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5260 - 5266
[4] Synlett, 2010, # 5, p. 715 - 720
  • 12
  • [ 71989-23-6 ]
  • [ 138775-22-1 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 44, p. 6109 - 6112
Same Skeleton Products
Historical Records

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[ 71989-23-6 ]

Davunetide Intermediates

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[ 71989-33-8 ]

Fmoc-Ser(tBu)-OH

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[ 132327-80-1 ]

Fmoc-Gln(Trt)-OH

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[ 68858-20-8 ]

Fmoc-Val-OH

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[ 35661-39-3 ]

Fmoc-Ala-OH

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[ 71989-31-6 ]

Fmoc-Pro-OH

Disomotide Intermediates

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[ 35661-40-6 ]

Fmoc-Phe-OH

Chemical Structure| 71989-33-8

[ 71989-33-8 ]

Fmoc-Ser(tBu)-OH

Chemical Structure| 68858-20-8

[ 68858-20-8 ]

Fmoc-Val-OH

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[ 71989-28-1 ]

Fmoc-Met-OH

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[ 71989-20-3 ]

Fmoc-Gln-OH

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