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Chemical Structure| 104719-63-3 Chemical Structure| 104719-63-3

Structure of Boc-D-Glu(OtBu)-OH
CAS No.: 104719-63-3

Chemical Structure| 104719-63-3

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Product Details of [ 104719-63-3 ]

CAS No. :104719-63-3
Formula : C14H25NO6
M.W : 303.35
SMILES Code : CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(O)=O
English Name :Boc-D-Glu(OtBu)-OH
MDL No. :MFCD00076927

Safety of [ 104719-63-3 ]

Computational Chemistry of [ 104719-63-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 21
Num. arom. heavy atoms 0
Fraction Csp3 0.79
Num. rotatable bonds 10
Num. H-bond acceptors 6.0
Num. H-bond donors 2.0
Molar Refractivity 77.02
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

101.93 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.83
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.72
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.09
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.34
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.22
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.84

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.14
Solubility 2.18 mg/ml ; 0.00717 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.48
Solubility 0.101 mg/ml ; 0.000334 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.95
Solubility 3.4 mg/ml ; 0.0112 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.93 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

3.41

Application In Synthesis of [ 104719-63-3 ]

* 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.

  • Downstream synthetic route of [ 104719-63-3 ]

[ 104719-63-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 13726-84-6 ]
  • [ 7689-03-4 ]
  • camptothecin-20 (S)-O-(N-(tert-butoxycarbonyl)-(D)-Glu(OtBu))Ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 2h; General procedure: EDCI (383.4 mg, 2 mmol) and DMAP (36 mg, 0.34 mmol) were added to a solution with CPT (139.2 mg, 0.4 mmol) and N-(tert-butoxycarbonyl) glycine (140.1 mg, 0.8 mmol) in dichloromethane (15 mL) and stirred at room temperature for 2 h. Chloroform (35 mL) was subsequently added, and the organic phase was washed with water (50 mL) and saturated sodium bicarbonate aqueous solution (50 mL), and then dried using Mg2SO4 before evaporating to dryness.
  • 2
  • [ 29022-11-5 ]
  • [ 35661-39-3 ]
  • [ 13726-84-6 ]
  • [ 71989-14-5 ]
  • [ 71989-38-3 ]
  • [ 71989-28-1 ]
  • [ 76-05-1 ]
  • [ 143824-78-6 ]
  • (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-fluorophenyl)propanoic acid [ No CAS ]
  • [Boc-D-Glu(tBu)-Ala-Tyr(tBu)-Gly-Trp(Boc)-Met-Asp(tBu)-Phe(4-F)-OH] monotrifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% General procedure: Peptides were synthesized by solid-phase peptide synthesis using the Fmoc/iBu-orthogonal strategy on a 2-chlorotritly chloride resin (100-200 mesh, 1% DVB, 1.6 mmol-g 1) or a Fmoc- Rink-Amid-2CT resin (200-400 mesh, 1 % DVB, 0.68 mmol-g 1). A peptide synthesis vessel was charged with 2-chlorotrityl chloride resin and DCM (30 ml. g 1 resin). The suspension was shaken with the aid of a Heidolph Vibramax 100 for 30 min at 23 C. The liquid was removed via vacuum filtration, and a solution of Fmoc-protected amino acid (4.00 equiv) and DIPEA (10.0 equiv) in DCM (30 ml. g 1 resin) was added into the peptide synthesis vessel. The resulting suspension was shaken for 15 hours at 23 C, and then the liquid was removed via vacuum filtration. The resin was washed with DCM (3 * 20 ml. g 1 resin * 2 min), and a solution of DIPEA, MeOH, and DCM (1 :2:17, v:v:v, 30 ml. g 1 resin) was added into the peptide synthesis vessel. The suspension was shaken for 1 hour at 23 C, and then the resin was washed sequentially with DMF (2 * 20 ml. g 1 resin), DCM (2 * 20 ml. g 1 resin), MeOH (2 * 20 ml. g 1 resin), and Et20 (2 * 20 ml. g 1 resin). The resin was dried under vacuum, and the loading efficiency was determined by UV-vis spectroscopy at 289.8 nm.9 General washing procedure: Into the peptide synthesis vessel containing resin was added the stated washing-solvent (20 ml. g 1 resin). The suspension was shaken for 2 minutes at 23 C, and then the liquid was removed via vacuum filtration. Into the peptide synthesis vessel containing resin-bound Fmoc-protected peptide was added 20% piperidine in DMF (v:v, 20 ml. g 1 resin), and the suspension was shaken for 5 minutes at 23 C. Then the liquid was removed via vacuum filtration. This deprotection sequence was repeated once, and then the resin was washed with DMF (3 x 20 ml. g 1 resin* 2 min). A round-bottom flask equipped with a Teflon-coated magnetic stirring bar was charged with Fmoc-protected amino acid (Fmoc-(AA)-OH, 4.00 equiv), HBTU (3.90 equiv), HOBt hydrate (3.90 equiv), DIPEA (8.00 equiv), and DMF (10 mL g 1 resin). The solution was stirred for 15 minutes at 23 C and was then added into the peptide synthesis vessel. The vessel was shaken for 90 minutes at 23 C, and then the liquid was removed via vacuum filtration. The resin was washed with DMF (3 x 10 ml_-g 1 resin x 2 min). A round-bottom flask equipped with a Teflon-coated magnetic stirring bar was charged with [Fmoc-Tyr(RuCp)-OH]-CF3C02 (S3) (2.00 equiv), HBTU (1.90 equiv), HOBt hydrate (1.90 equiv), DIPEA (16.0 equiv), and DMF (10 ml_-g 1 resin). The solution was stirred for 1 minute at 23 C and was then added into the peptide synthesis vessel. The vessel was shaken for 2 h at 23 C, and then the liquid was removed via vacuum filtration. The resin was washed with DMF (3 x 10 ml. g 1 resin x 2 min). The resin was washed with DCM (3 x 20 mL g 1 resin x 2 min). Then a solution of 20% of hexafluoroisopropanol (HFIP) in DCM (v:v) (50 mL g 1 resin) was added to the resin, and the suspension was shaken for 20 minutes at 23 C. The liquid was collected via vacuum filtration, and a solution of 20% of HFIP in DCM (v:v, 50 mL g 1 resin) was added to the resin, and the suspension was shaken for 50 minutes at 23 C. The liquid was collected via vacuum filtration, and the combined organic layers were concentrated in vacuo to dryness and were analyzed via LC-MS.
  • 3
  • [ 24424-99-5 ]
  • [ 104719-63-3 ]
  • [ 1407507-43-0 ]
YieldReaction ConditionsOperation in experiment
81% With dmap In <i>tert</i>-butyl alcohol at 20℃; for 0.5h; Inert atmosphere; Di-tert-butyl (N-tert-butoxycarbonyl)-L-glutamate ((S)-3) General procedure: Di-tert-butyldicarbonate(1.66 g, 1.74 mL, 7.59 mmol), and DMAP (296 mg, 2.42 mmol) were added to a stirred solutionof Boc-Glu(OtBu)-OH ((S)-4, 2.45 g, 8.07 mmol) in tert-butanol (20 mL) at room temperatureunder N2. After 30 min, the mixture was evaporated and the crude residue waschromatographed (silica gel, 5-10% EtOAc/n-hexane) to afford (S)-3 (2.64 g, 7.34 mmol, 97%)as a white solid.
  • 4
  • [ 104719-63-3 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
90% With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; 17.E Part E: To a stirred solution of Compound 70 (20 mg, 0.022 mmol), N-Boc-(D)- Glu(OtBu)-OH (10 mg, 0.033 mmol) and PyBOP (17 mg, 0.033 mmol) in DMF (2 mL) was added DIPEA (0.03 mL, 0.22 mmol), and the mixture was stirred at room temperature for 2 h. The mixture was concentrated, and the residue was purified over silica gel (DCM:MeOH 60:40 v/v) to afford Compound 71 (24 mg, 90% yield) as a white solid. ESI-MS m/z Calcd for C57H74N13O16 [M+H]+: 1196.53; found: 1196.55 [
 

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