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CAS No. : | 2389-60-8 | MDL No. : | MFCD00062271 |
Formula : | C19H28N2O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 380.44 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 27 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.53 |
Num. rotatable bonds : | 14 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 99.85 |
TPSA : | 113.96 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.6 cm/s |
Log Po/w (iLOGP) : | 3.2 |
Log Po/w (XLOGP3) : | 2.84 |
Log Po/w (WLOGP) : | 2.91 |
Log Po/w (MLOGP) : | 1.92 |
Log Po/w (SILICOS-IT) : | 2.07 |
Consensus Log Po/w : | 2.59 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.23 |
Solubility : | 0.225 mg/ml ; 0.000591 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.89 |
Solubility : | 0.00488 mg/ml ; 0.0000128 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.47 |
Solubility : | 0.0128 mg/ml ; 0.0000336 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.44 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; | N-α-Cbz-(S)-Lysine (5g, 17.85mmol) was dissolved in a mixture of THF (5OmL) and water (5OmL). To this sodium bicarbonate (3g, 35.5mmol, 2eq) and a solution OfBoC2O (9g, 41mmol, 2.3eq) in THF (5OmL). After stirring at room temperature overnight, the THF was removed under reduced pressure and the resulting aqueous solution was neutralized with 2N HCl. This was extracted with ethyl acetate and the combined organic layers were washed with brine. The organic layer was dried with sodium sulfate and concentrated to a clear oil. Removal of excess BoC2O by Kugelrhor distillation resulted in a thick clear oil weighing 6.Sg, 100percent. 1HNMR (CDCl3) δ 11.6 (s, IH), 7.32 (s, 5H)5 6.36 (s, IH)5 5.75 (d, IH5 J=8)5 5.09 (s, 2H)5 4.37(m5 IH), 3.06 (m, 2H), 1.78 (m, 2H)5 1.53 (s, 4H)5 1.42 (s, 9H). 13C NMR (CDCl3) δ 174.8, 155.4, 135.4, 127.6, 127.3, 127.2, 78.6, 66.1, 52.9, 39.2, 31.0, 28.6, 27.5, 26.6, 21.4 |
100% | Stage #1: With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; Stage #2: With hydrogenchloride In water |
a. Synthesis of Compound 1 (NBoc-Cbz Lysine) N-?-Cbz-(S)-Lysine (5 g, 17.85 mmol) was dissolved in a mixture of THF (50 mL) and water (50 mL). To this sodium bicarbonate (3 g, 35.5 mmol, 2 eq) and a solution of Boc2O (9 g, 41 mmol, 2.3 eq) in THF (50 mL). After stirring at room temperature overnight, the THF was removed under reduced pressure and the resulting aqueous solution was neutralized with 2N HCl. This was extracted with ethyl acetate and the combined organic layers were washed with brine. The organic layer was dried with sodium sulfate and concentrated to a clear oil. Removal of excess Boc2O by Kugelrhor distillation resulted in a thick clear oil weighing 6.8 g, 100percent. 1H NMR (CDCl3) ? 11.6 (s, 1H), 7.32 (s, 5H), 6.36 (s, 1H), 5.75 (d, 1H, J=8), 5.09 (s, 2H), 4.37 (m, 1H), 3.06 (m, 2H), 1.78 (m, 2H), 1.53 (s, 4H), 1.42 (s, 9H). 13C NMR (CDCl3) ? 174.8, 155.4, 135.4, 127.6, 127.3, 127.2, 78.6, 66.1, 52.9, 39.2, 31.0, 28.6, 27.5, 26.6, 21.4 |
100% | Stage #1: With sodium hydrogencarbonate In tetrahydrofuran at 20℃; |
Example 6. Synthesis of Lysine Teroxazole Intermediate 309; A lysine teroxazole intermediate that can be used to prepare compounds of the invention can be prepared as follows <n="50"/>a. Synthesis of Compound 301 (NBoc-Cbz Lysine)N-α-Cbz-(S)-Lysine (5g, 17.85mmol) was dissolved in a mixture of THF (5OmL) and water (5OmL). To this sodium bicarbonate (3g, 35.5mmol, 2eq) and a solution of BoC2O (9g, 41mmol, 2.3eq) in THF (5OmL). After stirring at room temperature overnight, the THF was removed under reduced pressure and the resulting aqueous solution was neutralized with 2N HCl. This was extracted with ethyl acetate and the combined organic layers were washed with brine. The organic layer was dried with sodium sulfate and concentrated to a clear oil. Removal of excess BoC2O by Kugelrhor distillation resulted in a thick clear oil weighing 6.8g, 100percent. H NMR (CDCl3) δ 11.6 (s, IH), 7.32 (s, 5H), 6.36 (s, IH), 5.75 (d, IH, J=8), 5.09 (s, 2H), 4.37(m, IH), 3.06 (m, 2H), 1.78 (m, 2H), 1.53 (s, 4H), 1.42 (s, 9H). 13C NMR (CDCl3) δ 174.8, 155.4, 135.4, 127.6, 127.3, 127.2, 78.6, 66.1, 52.9, 39.2, 31.0, 28.6, 27.5, 26.6, 21.4. |
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