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[ CAS No. 26054-60-4 ] {[proInfo.proName]}

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Chemical Structure| 26054-60-4
Chemical Structure| 26054-60-4
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Product Details of [ 26054-60-4 ]

CAS No. :26054-60-4 MDL No. :MFCD01318309
Formula : C11H11NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :CWFZPRQDHIUBDO-VIFPVBQESA-N
M.W : 221.21 Pubchem ID :489182
Synonyms :

Calculated chemistry of [ 26054-60-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.28
TPSA : 64.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 1.17
Log Po/w (WLOGP) : 0.69
Log Po/w (MLOGP) : 0.76
Log Po/w (SILICOS-IT) : 1.16
Consensus Log Po/w : 1.09

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.9
Solubility : 2.81 mg/ml ; 0.0127 mol/l
Class : Very soluble
Log S (Ali) : -2.12
Solubility : 1.67 mg/ml ; 0.00754 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.78
Solubility : 0.368 mg/ml ; 0.00166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.61

Safety of [ 26054-60-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 26054-60-4 ]

* 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 [ 26054-60-4 ]
  • Downstream synthetic route of [ 26054-60-4 ]

[ 26054-60-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 26054-60-4 ]
  • [ 3536-96-7 ]
  • [ 78553-51-2 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, # 15, p. 4649 - 4659
  • 2
  • [ 26054-60-4 ]
  • [ 74-89-5 ]
  • [ 19647-68-8 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 41, p. 7605 - 7608
  • 3
  • [ 1145-80-8 ]
  • [ 26054-60-4 ]
YieldReaction ConditionsOperation in experiment
72% With dimethyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; acetonitrile at -55℃; for 2 h; Inert atmosphere Example 4; Standard Procedure for the Synthesis of Ddz-Dap(Boc-Me)-OH (Ddz-AA4, FIG. 2); Step 4-1. Z-Serine-β-lactone (AA4-2).; This intermediate was prepared in an analogous fashion to that described previously for the Boc derivative AA3-1. In a dry 250 mL 3-neck flask equipped with a mechanical stirrer under nitrogen atmosphere was added triphenylphosphine (4.5 g, 17.1 mmol, 1.1 eq.), followed by 100 mL of an anhydrous THF:CH3CN (1:9) solvent mixture. The mixture was stirred until a solution was obtained and then cooled to -55° C. (bath temperature) and dimethylazodicarboxylate (DMAD, 1.9 mL, 17.1 mmol, 1.1 eq) was added dropwise over 10 min. After completion of the addition, the mixture was stirred for 20 min, then a solution of Z-Ser-OH (AA4-1, 3.7 g, 15.5 mmol, 1.0 eq) in 50 mL of anhydrous THF:CH3CN (1:9) was added dropwise over 30 min. The reaction mixture was stirred at -55° C. for 1.5 h, then the cooling bath removed and the solution allowed to warm slowly to room temperature. Once the mixture reached room temperature, the solvent was evaporated under reduced pressure. The resulting yellow oil was purified by flash chromatography [gradient, hexanes/EtOAc, (80:20) to (60:40)] to give 2.5 g of AA4-2 as a white solid in 72percent yield. Purification of the crude oil is preferentially performed the same day to avoid decomposition. DCM can be added to help solubilize the residue.TLC (hexanes/EtOAc (60/40): Rf=0.55 (UV, CMA)
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 22, p. 2643 - 2646
[2] Patent: US2010/93720, 2010, A1, . Location in patent: Page/Page column 38
[3] Journal of the American Chemical Society, 1985, vol. 107, # 24, p. 7105 - 7109
[4] Organic and Biomolecular Chemistry, 2008, vol. 6, # 18, p. 3240 - 3243
[5] Organic Syntheses, 1992, vol. 70, p. 1 - 1
[6] Canadian Journal of Chemistry, 1986, vol. 64, p. 706 - 713
[7] Canadian Journal of Chemistry, 1986, vol. 64, p. 706 - 713
[8] Synthetic Communications, 1995, vol. 25, # 16, p. 2475 - 2482
[9] Journal of Medicinal Chemistry, 1997, vol. 40, # 24, p. 3979 - 3985
[10] Journal of Organic Chemistry, 2002, vol. 67, # 5, p. 1536 - 1547
[11] Chemistry Letters, 1982, p. 45 - 48
[12] Patent: US2010/22605, 2010, A1, . Location in patent: Page/Page column 49-50
  • 4
  • [ 1145-80-8 ]
  • [ 1972-28-7 ]
  • [ 26054-60-4 ]
YieldReaction ConditionsOperation in experiment
45% With triphenylphosphine In acetonitrile a
L-2-Amino-3-phenylaminoethylpropionic Acid
54.8 g (0.209 mol) of triphenylphosphine were suspended in 600 ml of acetonitrile and, with exclusion of moisture, cooled to -35° C. to -45° C.
At this temperature, 36.4 g (0.209 mol) of diethyl azodicarboxylate were then added dropwise over a period of 50 min.
The mixture was stirred at -35° C. for another 15 min.
A solution of 50 g (0.209 mol) of N-benzyloxycarbonyl-L-serine in 500 ml of acetonitrile was added dropwise to this mixture, the temperature being kept below -35° C.
The mixture was then allowed to react at 5° C. for another 12 h and warmed to RT.
The reaction solution was freed from solvent under reduced pressure and the crude product was purified by medium pressure chromatography over silica gel (DCM/AcCN: 25/1).
Removal of the solvent gave 20.8 g (yield 45percent) of pure N-benzyloxy-carbonyl-L-serine-β-lactone (see also Org. Synth. 1991 (70) 1ff.) in fine needles.
Empirical formula C11H11NO4; M.W.=221.2; MS (M+H) 222.1.
Reference: [1] Patent: US2003/119820, 2003, A1,
  • 5
  • [ 81187-75-9 ]
  • [ 26054-60-4 ]
Reference: [1] Chemistry Letters, 1982, p. 45 - 48
  • 6
  • [ 26054-60-4 ]
  • [ 35761-26-3 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 41, p. 7605 - 7608
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