Home Cart Sign in  
Chemical Structure| 57133-29-6 Chemical Structure| 57133-29-6

Structure of Boc-Orn(Boc)-OH
CAS No.: 57133-29-6

Chemical Structure| 57133-29-6

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 57133-29-6 ]

CAS No. :57133-29-6
Formula : C15H28N2O6
M.W : 332.39
SMILES Code : O=C(O)[C@@H](NC(OC(C)(C)C)=O)CCCNC(OC(C)(C)C)=O
MDL No. :MFCD00151882
InChI Key :RJOJSMIZZYHNQG-JTQLQIEISA-N
Pubchem ID :7015803

Safety of [ 57133-29-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 57133-29-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 23
Num. arom. heavy atoms 0
Fraction Csp3 0.8
Num. rotatable bonds 12
Num. H-bond acceptors 6.0
Num. H-bond donors 3.0
Molar Refractivity 85.02
TPSA ?

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

113.96 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.29
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

1.98
Log Po/w (WLOGP)?

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

2.27
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.

1.21
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

0.92
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.73

Water Solubility

Log S (ESOL):?

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

-2.36
Solubility 1.46 mg/ml ; 0.0044 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.

-4.0
Solubility 0.0333 mg/ml ; 0.0001 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

-2.39
Solubility 1.35 mg/ml ; 0.00406 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

Yes
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.

-6.92 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

1.0
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)

3.36

Application In Synthesis of [ 57133-29-6 ]

* 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.

  • Downstream synthetic route of [ 57133-29-6 ]

[ 57133-29-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 57133-29-6 ]
  • [ 84605-18-5 ]
  • [ 1255152-12-5 ]
  • [ 1255151-91-7 ]
  • C60H102N4O15 [ No CAS ]
YieldReaction ConditionsOperation in experiment
8% Preparation of 15a, 15b, 15c: : (Boc)2-(L) Ornithine-OH (4.5 g, 13.6 mmols) (Bachem, Torrance, Calif.) was dissolved in 15 ml of DCM. To this was added 2.5 g (13.6 mmol) of pentafluorophenol. The reaction was cooled in an ice-bath followed by slow addition of 2.2 ml (13.6 mmols) of DIC. After complete addition the reaction mixture was stirred at room temperature for 30 minutes at which time the reaction mixture turned turbid (diisopropylcarbodimide-urea precipitation). To this mixture was then added 700 mg (1.43 mmols) of 2 followed by 1.6 g (13.6 mmol) of DMAP and the reaction was stirred at room temperature for 24 hours. The reaction mixture was transferred into a separatory funnel and washed with H2O (2×) 1% aq. HCl (2×), 0.1N aq. NaOH (2×), sat. NaHCO3 (3×), H2O (1×) and brine (1×), the organic layer was separated, dried over Na2SO4, filtered and the solvent was evaporated under vacuum. To the residue was then added 25 ml of diethylether and the urea was precipitated out. The filtrate was evaporated and the residue was purified using flash chromatography with solvent gradient of 2%-5% MeOH in DCM to furnish 690 mg (60%) of a mixture of products 15a, 15b, 15c, and 120 mg (8%) of the C3, C6 bis product.The 1HNMR showed major amounts of 15a and 15b products with 2% of the regioisomer 15c. 1HNMR of the mixture(15a, 15b and 15c): (CDCl3) delta ppm: 0.38 (1H, bs), 0.52 (1H, bs), 0.90-1.38 (m, 26H), 1.39-1.45 (s,m 27H), 1.59-1.63 (m, 5H), 1.76-1.82 (m, 2H), 1.96-2.01 (m, 4H), 2.16-2.20 (m, IH), 2.30-2.35 (d, 1H), 2.49-2.54 (q, 1H), 3.10-3.19 (m, 6H), 3.19-3.22 (m, 1H), 3.45-3.57 (t, 1H), 3.71-3.76 (m, 1H), 4.19-4.21 (m, 1H), 4.22-4.30 (m, 1H), 4.52-4.60 (m, 1H), 4.61-4.65 (m, 1H), 4.79-4.81 (m, 1H), 4.95-5.01 (m, 1H), 5.13-5.21 (m, 1H), 5.38-5.41 (m, 1H). MS (M+H) 804
  • 2
  • [ 57133-29-6 ]
  • [ 84605-18-5 ]
  • 2-(L),5-diamino-pentanoic acid 3β,16β-dihydroxy-17-[5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,13,14-tetramethyl-tetradecahdro-cyclopropa[9,10]cyclopenta[a]phenanthren-6α-yl ester dihydrochloride [ No CAS ]
  • 2-(L),5-diamino-pentanoic acid 6α,16β-dihydroxy-17-[5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3β-yl ester dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Preparation of 15a, 15b, 15c: : (Boc)2-(L) Ornithine-OH (4.5 g, 13.6 mmols) (Bachem, Torrance, Calif.) was dissolved in 15 ml of DCM. To this was added 2.5 g (13.6 mmol) of pentafluorophenol. The reaction was cooled in an ice-bath followed by slow addition of 2.2 ml (13.6 mmols) of DIC. After complete addition the reaction mixture was stirred at room temperature for 30 minutes at which time the reaction mixture turned turbid (diisopropylcarbodimide-urea precipitation). To this mixture was then added 700 mg (1.43 mmols) of 2 followed by 1.6 g (13.6 mmol) of DMAP and the reaction was stirred at room temperature for 24 hours. The reaction mixture was transferred into a separatory funnel and washed with H2O (2×) 1% aq. HCl (2×), 0.1N aq. NaOH (2×), sat. NaHCO3 (3×), H2O (1×) and brine (1×), the organic layer was separated, dried over Na2SO4, filtered and the solvent was evaporated under vacuum. To the residue was then added 25 ml of diethylether and the urea was precipitated out. The filtrate was evaporated and the residue was purified using flash chromatography with solvent gradient of 2%-5% MeOH in DCM to furnish 690 mg (60%) of a mixture of products 15a, 15b, 15c, and 120 mg (8%) of the C3, C6 bis product.The 1HNMR showed major amounts of 15a and 15b products with 2% of the regioisomer 15c. 1HNMR of the mixture(15a, 15b and 15c): (CDCl3) delta ppm: 0.38 (1H, bs), 0.52 (1H, bs), 0.90-1.38 (m, 26H), 1.39-1.45 (s,m 27H), 1.59-1.63 (m, 5H), 1.76-1.82 (m, 2H), 1.96-2.01 (m, 4H), 2.16-2.20 (m, IH), 2.30-2.35 (d, 1H), 2.49-2.54 (q, 1H), 3.10-3.19 (m, 6H), 3.19-3.22 (m, 1H), 3.45-3.57 (t, 1H), 3.71-3.76 (m, 1H), 4.19-4.21 (m, 1H), 4.22-4.30 (m, 1H), 4.52-4.60 (m, 1H), 4.61-4.65 (m, 1H), 4.79-4.81 (m, 1H), 4.95-5.01 (m, 1H), 5.13-5.21 (m, 1H), 5.38-5.41 (m, 1H). MS (M+H) 804 Preparation of 16a, 16b, 16c To a 200 mg (0.25 mmol) of the mixture of 15a, 15b, 15c, was added 10 ml of 1.0M HCl/diethylether and strirred for 16 hrs. The white solids were filtered and washed with 10 ml of Et2O (4×). The solids were then dried under high vacuum for overnight to yield 160 mg (95%) of the target products 16a, 16b, 16c, as a white powder. The 1HNMR showed major amounts of 16a and 16b products with 2% of the C-16 (16c) regioisomer.1HNMR of the mixture (16a, 16b and 16c): (D2O) delta ppm: 0.26 (1H, bs), 0.52 (1H, bs), 0.90-1.18 (m, 26H), 1.49-1.74 (m, 5H), 1.83-2.10 (m, 2H), 2.20-2.31 (m, 4H), 2.81-2.92 (m, 2H), 3.19-3.20 (m, 1H), 3.39-3.42 (m, 1H), 3.62-3.71 (m, 1H), 3.88-4.00 (m, 1H), 4.08-4.12 (m, 1H), 4.52-4.57 (m, 1H), 4.61-4.65 (m, 1H), 4.79-4.81 (m, 1H). MS (M+H): 605.
 

Historical Records

Categories