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Chemical Structure| 35661-60-0
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Product Details of [ 35661-60-0 ]

CAS No. :35661-60-0 MDL No. :MFCD00037133
Formula : C21H23NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :CBPJQFCAFFNICX-IBGZPJMESA-N
M.W : 353.41 Pubchem ID :1549133
Synonyms :
Fmoc-leucine;N-FMOC-leucine;FMOC-Leu;FMOC-L-Leucine;NSC 334290;NPC 15199

Calculated chemistry of [ 35661-60-0 ]      Expand+

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 : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.43
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 : 3.48

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 : 3.86

Safety of [ 35661-60-0 ]

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 [ 35661-60-0 ]

* 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 [ 35661-60-0 ]
  • Downstream synthetic route of [ 35661-60-0 ]

[ 35661-60-0 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 35661-60-0 ]
  • [ 687-51-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2841 - 2849
  • 2
  • [ 35661-60-0 ]
  • [ 71989-23-6 ]
  • [ 36077-41-5 ]
Reference: [1] Marine Drugs, 2013, vol. 11, # 12, p. 4834 - 4857
  • 3
  • [ 61-90-5 ]
  • [ 35661-60-0 ]
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
  • 4
  • [ 61-90-5 ]
  • [ 82911-69-1 ]
  • [ 35661-60-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1995, # 4, p. 723 - 730
[2] Synthetic Communications, 2009, vol. 39, # 11, p. 2022 - 2031
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 2980 - 2983
[4] Tetrahedron Letters, 2017, vol. 58, # 16, p. 1600 - 1603
  • 5
  • [ 61-90-5 ]
  • [ 28920-43-6 ]
  • [ 35661-60-0 ]
Reference: [1] Journal of Organic Chemistry, 1972, vol. 37, # 22, p. 3404 - 3409
[2] Journal of the Chinese Chemical Society, 2011, vol. 58, # 4, p. 509 - 515
[3] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 592 - 609
  • 6
  • [ 28920-43-6 ]
  • [ 35661-60-0 ]
Reference: [1] Helvetica Chimica Acta, 1992, vol. 75, # 8, p. 2572 - 2582
[2] Patent: US4128540, 1978, A,
[3] Synlett, 2011, # 14, p. 2013 - 2016
  • 7
  • [ 146549-16-8 ]
  • [ 35661-60-0 ]
Reference: [1] Helvetica Chimica Acta, 1992, vol. 75, # 8, p. 2572 - 2582
  • 8
  • [ 61-90-5 ]
  • [ 28920-43-6 ]
  • [ 35661-60-0 ]
Reference: [1] Patent: US5079260, 1992, A,
  • 9
  • [ 103321-59-1 ]
  • [ 35661-60-0 ]
  • [ 139551-97-6 ]
YieldReaction ConditionsOperation in experiment
36% With ammonia In tetrahydrofuran; ethanol; water EXAMPLE 22
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-leucine Amide (NPC 15528)
A solution of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine, acid chloride (3.5 g, 10 mmol) in 10 mL of THF was charged with NH3 (29.6percent water solution, 1.26 mL, 20 mmol) at room temperature.
The reaction mixture was stirred for 30 min., then diluted with 100 mL of water and extracted with ethyl acetate (5*20 mL).
The organic layers were combined, extracted with 10percent potassium carbonate solution, washed with water, brine, dried and evaporated.
Recrystallization of the product from ethanol afforded 1.26 g (36percent) of N-(9-fluorenylmethoxycarbonyl)-L-leucine, amide as colorless solid, mp 79°-80° C.
Reference: [1] Patent: US5079260, 1992, A,
  • 10
  • [ 61-90-5 ]
  • [ 1131148-55-4 ]
  • [ 35661-60-0 ]
Reference: [1] Synlett, 2011, # 14, p. 2013 - 2016
  • 11
  • [ 61-90-5 ]
  • [ 35661-60-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3103 - 3108
  • 12
  • [ 61-90-5 ]
  • [ 88744-04-1 ]
  • [ 35661-60-0 ]
Reference: [1] Synthesis, 1986, # 4, p. 303 - 305
  • 13
  • [ 61-90-5 ]
  • [ 102774-86-7 ]
  • [ 35661-60-0 ]
Reference: [1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098
  • 14
  • [ 168958-29-0 ]
  • [ 35661-60-0 ]
Reference: [1] Helvetica Chimica Acta, 1992, vol. 75, # 8, p. 2572 - 2582
  • 15
  • [ 127556-09-6 ]
  • [ 35661-60-0 ]
Reference: [1] Helvetica Chimica Acta, 1992, vol. 75, # 8, p. 2572 - 2582
  • 16
  • [ 28920-43-6 ]
  • [ 760-84-9 ]
  • [ 35661-60-0 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10575 - 10582
  • 17
  • [ 1227363-07-6 ]
  • [ 28920-43-6 ]
  • [ 29022-11-5 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • [ 35661-38-2 ]
  • [ 135248-89-4 ]
Reference: [1] Journal of Physical Chemistry B, 2010, vol. 114, # 19, p. 6751 - 6762
  • 18
  • [ 61-90-5 ]
  • [ 82911-69-1 ]
  • [ 35661-60-0 ]
  • [ 35737-10-1 ]
  • [ 24324-17-2 ]
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 16, p. 1600 - 1603
  • 19
  • [ 61-90-5 ]
  • [ 82911-69-1 ]
  • [ 35661-60-0 ]
  • [ 35737-10-1 ]
  • [ 24324-17-2 ]
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 16, p. 1600 - 1603
  • 20
  • [ 29022-11-5 ]
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  • [ 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
  • 21
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  • [ 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
  • 22
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  • [ 67436-13-9 ]
  • [ 115057-30-2 ]
  • [ 71989-31-6 ]
  • [ 50-56-6 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 46, p. 5651 - 5654
  • 23
  • [ 50-00-0 ]
  • [ 35661-60-0 ]
  • [ 103478-62-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 24, p. 5878 - 5881
[2] Marine Drugs, 2016, vol. 14, # 9,
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 6, p. 1232 - 1238
  • 24
  • [ 50-00-0 ]
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  • [ 103478-62-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4581 - 4589
  • 25
  • [ 35661-60-0 ]
  • [ 103478-62-2 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 8, p. 2068 - 2073
  • 26
  • [ 35661-60-0 ]
  • [ 139551-83-0 ]
YieldReaction ConditionsOperation in experiment
91%
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 0.4 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] Journal of Organic Chemistry, 2001, vol. 66, # 25, p. 8454 - 8462
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 1, p. 117 - 120
[3] Organic and Biomolecular Chemistry, 2010, vol. 8, # 21, p. 4855 - 4860
[4] Tetrahedron Letters, 2012, vol. 53, # 38, p. 5059 - 5063
[5] Organic Letters, 2008, vol. 10, # 10, p. 1881 - 1884
[6] Organic and Biomolecular Chemistry, 2011, vol. 9, # 11, p. 4182 - 4187
[7] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 6994 - 6996
[8] Tetrahedron Asymmetry, 1998, vol. 9, # 11, p. 1855 - 1858
[9] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5260 - 5266
[10] Synthetic Communications, 2009, vol. 39, # 19, p. 3555 - 3566
[11] Synlett, 2010, # 5, p. 715 - 720
[12] Organic and Biomolecular Chemistry, 2011, vol. 9, # 11, p. 4182 - 4187
[13] ChemMedChem, 2013, vol. 8, # 7, p. 1041 - 1056
[14] ACS Combinatorial Science, 2017, vol. 19, # 3, p. 131 - 136
  • 27
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Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4581 - 4589
  • 28
  • [ 186581-53-3 ]
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  • [ 193887-44-4 ]
Reference: [1] Chemical communications (Cambridge, England), 2001, # 22, p. 2330 - 2331
  • 29
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  • [ 193887-44-4 ]
Reference: [1] Helvetica Chimica Acta, 1998, vol. 81, # 2, p. 187 - 206
[2] Synthesis, 1998, # 6, p. 837 - 841
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