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[ CAS No. 35661-40-6 ]

{[proInfo.proName]} (Synonyms:Fmoc-Phe-OH) ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 35661-40-6
Chemical Structure| 35661-40-6
Structure of 35661-40-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 35661-40-6 ]

CAS No. :35661-40-6 MDL No. :MFCD00037128
Formula : C24H21NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :SJVFAHZPLIXNDH-QFIPXVFZSA-N
M.W :387.43 Pubchem ID :978331
Synonyms :
Fmoc-Phe-OH

Calculated chemistry of [ 35661-40-6 ]

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.17
Num. rotatable bonds : 8
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 109.66
TPSA : 75.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.58
Log Po/w (XLOGP3) : 4.64
Log Po/w (WLOGP) : 4.22
Log Po/w (MLOGP) : 3.42
Log Po/w (SILICOS-IT) : 4.04
Consensus Log Po/w : 3.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.1
Solubility : 0.0031 mg/ml ; 0.00000801 mol/l
Class : Moderately soluble
Log S (Ali) : -5.95
Solubility : 0.00043 mg/ml ; 0.00000111 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.38
Solubility : 0.0000162 mg/ml ; 0.0000000419 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.68

Safety of [ 35661-40-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P273-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335-H413 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 35661-40-6 ]

* 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 [ 35661-40-6 ]
  • Downstream synthetic route of [ 35661-40-6 ]

[ 35661-40-6 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 35661-40-6 ]
  • [ 5241-58-7 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1988, # 5, p. 382 - 384
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2841 - 2849
  • 2
  • [ 35661-40-6 ]
  • [ 129397-83-7 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 0℃; for 0.166667 h;
Stage #2: With sodium tetrahydroborate In water; ethyl acetate at 0℃; for 0.416667 h;
General procedure: To a solution of carboxylic acid (10 mmol) in THF (10 mL), DIPEA (11 mmol, 1.42 mL) and 50percent T3P in EtOAc (20 mmol, 6.36 mL) were added at 0 °C and the solution was stirred for about 10 min. Then aqueous solution of NaBH4 (10 mmol, 388 mg in 0.3 mL of H2O) was added to the reaction mixture at the same temperature and the reaction was allowed to stir till the completion of the reaction as indicated by TLC. After the completion of the reaction, the solvent was evaporated and the crude alcohol was extracted into EtOAc and the organic phase was washed with 5percent citric acid (10 mL .x. 2), 5percent Na2CO3 (10 mL .x. 2), water, and brine solution. The product was isolated after the evaporation of solvent under reduced pressure and dried over anhydrous Na2SO4.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 38, p. 5059 - 5063
[2] Journal of Organic Chemistry, 2001, vol. 66, # 25, p. 8454 - 8462
[3] Tetrahedron Letters, 2000, vol. 41, # 32, p. 6131 - 6135
[4] Organic Letters, 2008, vol. 10, # 10, p. 1881 - 1884
[5] Tetrahedron Letters, 1999, vol. 40, # 23, p. 4395 - 4396
[6] Tetrahedron Asymmetry, 1998, vol. 9, # 11, p. 1855 - 1858
[7] Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2313 - 2316
[8] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5260 - 5266
[9] Synthetic Communications, 2009, vol. 39, # 19, p. 3555 - 3566
[10] Journal of Organic Chemistry, 2014, vol. 79, # 17, p. 8422 - 8427
[11] ACS Combinatorial Science, 2017, vol. 19, # 3, p. 131 - 136
[12] Organic and Biomolecular Chemistry, 2018, vol. 16, # 26, p. 4874 - 4880
  • 3
  • [ 35661-40-6 ]
  • [ 244633-31-6 ]
  • [ 86060-92-6 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 32, p. 5939 - 5942
  • 4
  • [ 771-61-9 ]
  • [ 35661-40-6 ]
  • [ 86060-92-6 ]
Reference: [1] Synthesis, 1983, # 4, p. 325 - 327
[2] Synthesis, 1986, # 4, p. 303 - 305
  • 5
  • [ 14533-84-7 ]
  • [ 35661-40-6 ]
  • [ 86060-92-6 ]
Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 41, p. 5851 - 5852
  • 6
  • [ 35661-40-6 ]
  • [ 96157-57-2 ]
  • [ 86060-92-6 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1989, vol. 37, # 12, p. 2539 - 2541
  • 7
  • [ 35661-40-6 ]
  • [ 86060-92-6 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 43, p. 6199 - 6202
  • 8
  • [ 126727-04-6 ]
  • [ 35661-40-6 ]
  • [ 86123-10-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 38, p. 11214 - 11218[2] Angew. Chem., 2016, vol. 127, # 38, p. 11366 - 11370,5
[3] Chirality, 2018, vol. 30, # 9, p. 1067 - 1078
  • 9
  • [ 50-00-0 ]
  • [ 35661-40-6 ]
  • [ 77128-73-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 24, p. 5878 - 5881
  • 10
  • [ 35661-40-6 ]
  • [ 77128-73-5 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 31, p. 6186 - 6192
[2] European Journal of Organic Chemistry, 2013, # 21, p. 4509 - 4513
[3] Tetrahedron, 2014, vol. 70, # 14, p. 2351 - 2358
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 6, p. 1163 - 1170
  • 11
  • [ 35661-40-6 ]
  • [ 169624-67-3 ]
YieldReaction ConditionsOperation in experiment
16.2 mg
Stage #1: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.833333 h;
Stage #2: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 16 h;
Stage #3: With trifluoroacetic acid In dichloromethane; N,N-dimethyl-formamide for 1 h;
General procedure: The Fmoc-amino acid-Wang resin (300 mg) was suspended in a 30percent piperidine solution in DMF and stirred 50 min at r.t (room temperature).The resin was washed with CH2Cl2 (3×2 mL), EtOAc(3×2 mL), MeOH (3×2 mL) and CH2Cl2 (2 mL), and finally dried in vacuum. The resin was suspended in 5 mL of a DMF:DCM (2:1) mixture and Fmoc-amino acid (3 equiv.), 1-hydroxybenzotriazole (3 equiv.), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (3 equiv.) and diisopropylethylamine(3 equiv.) were successively added. The solution was stirred at r.t. for 16 h. After this, the resin was washed with DMF(3×2 mL), CH2Cl2 (3×2 mL), MeOH (3×2 mL) and CH2Cl2 (2 mL), and finally dried in vacuum. Resin was treated with 5 mL of 10percent TFA in CH2Cl2 for 1 h. The mixture was filtered and the filtrate was evaporated under reduced pressure to give the crude product.
Reference: [1] Bioorganic Chemistry, 2018, vol. 81, p. 211 - 221
  • 12
  • [ 7364-42-3 ]
  • [ 35661-40-6 ]
  • [ 169624-67-3 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 6, p. 2689 - 2702
  • 13
  • [ 35661-40-6 ]
  • [ 169624-67-3 ]
Reference: [1] Rapid Communications in Mass Spectrometry, 2011, vol. 25, # 14, p. 1949 - 1958
  • 14
  • [ 35661-40-6 ]
  • [ 193954-28-8 ]
Reference: [1] Helvetica Chimica Acta, 1998, vol. 81, # 2, p. 187 - 206
[2] Synthesis, 1998, # 6, p. 837 - 841
  • 15
  • [ 35661-40-6 ]
  • [ 84889-09-8 ]
Reference: [1] Journal of Peptide Science, 2013, vol. 19, # 5, p. 315 - 324
[2] Soft Matter, 2013, vol. 9, # 18, p. 4672 - 4680
[3] Chemical Communications, 2015, vol. 51, # 25, p. 5253 - 5256
[4] Macromolecular Bioscience, 2017, vol. 17, # 4,
[5] Organic Process Research and Development, 2017, vol. 21, # 10, p. 1533 - 1541
[6] Patent: KR2018/99205, 2018, A, . Location in patent: Paragraph 0076-0084
  • 16
  • [ 63-91-2 ]
  • [ 35661-40-6 ]
  • [ 84889-09-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 8, p. 1277 - 1281
  • 17
  • [ 98-97-5 ]
  • [ 35661-40-6 ]
  • [ 179324-69-7 ]
Reference: [1] RSC Advances, 2018, vol. 8, # 6, p. 3343 - 3347
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