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CAS No. : | 57224-63-2 | MDL No. : | MFCD00038585 |
Formula : | C13H17NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OPZWAOJFQFYYIX-KOLCDFICSA-N |
M.W : | 267.28 | Pubchem ID : | 2733409 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.38 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 67.17 |
TPSA : | 84.86 Ų |
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) : | -7.12 cm/s |
Log Po/w (iLOGP) : | 1.87 |
Log Po/w (XLOGP3) : | 1.14 |
Log Po/w (WLOGP) : | 0.68 |
Log Po/w (MLOGP) : | 0.89 |
Log Po/w (SILICOS-IT) : | 0.95 |
Consensus Log Po/w : | 1.11 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.92 |
Solubility : | 3.21 mg/ml ; 0.012 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.52 |
Solubility : | 0.814 mg/ml ; 0.00305 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.53 |
Solubility : | 0.789 mg/ml ; 0.00295 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.21 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
89.1% | With sodium hydrogencarbonate; sodium hydroxide In water | The In a 2L beaker, 100 g of L-threonine methyl ester hydrochloride, 600 ml of water and adjusted to pH of sodium bicarbonate were added dropwise, and z-cl 110 g was added dropwise and the pH was adjusted with 2 moc / l sodium hydroxide 8-9 reaction. The reaction was terminated, 1L of ethyl acetate was added, 500ML washed with water, washed with 500ml of saturated brine, dried over 100g of anhydrous sodium sulfate, filtered and evaporated to a solid solution under reduced pressure. The granite was crystallized at 600Ml, filtered and dried to obtain z-thr-ome 140 g, yield 89.1percent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 h; | General procedure: A solution of N-benzyloxycarbonyl-L-amino acid S5 (7.9 mmol) in DMF (20 ml) was added methyliodide (1.1 g, 7.9 mmol) and potassium carbonate (1.2 g, 8.7 mmol). The reaction mixture waskept at room temperature for 3 hours. The methylated products were purified by column chromatographyin the yields of 50percent (1.0 g, colorless-oil) for serine and 92percent (1.9 g, white-solid) for threonine.The methylated amino acid (4.0 mmol) in DMF (10 ml) was mixed with TBDPSCl (2.2 g, 7.9mmol), imidazole (810 mg, 11.9 mmol) and catalytic amount of DMAP. The reaction was processedat 45 °C for 7 hours. The desired products were purified by column chromatography in theyields of 90percent (1.7 g, colorless-oil) for serine and 90percent (1.8 g, white-solid) for threonine. The silylproduct (500 mg, 1.0 mmol) in DMF (1 ml) was reacted with 15percent NaOH (5 ml) for 2 hours. Thereaction mixture was quenching by 1 N HCl(aq) and 6 was extracted by ethyl acetate. The desiredamino acid 6 was obtained after removal of ethyl acetate in the quantitative yields (470 mg,white-solid for serine; 486 mg, colorless-oil for threonine). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70 g | With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 13 h; | [00283] To a stirring solution of 6S-X (60 g, 353 mmol) in water/1,4 dioxane (150 m l. 300 ml.) The reaction mixture was cooled to 0 CC added NaHCO -, (88.9 g, 1.059 mol) at 0 C and stirred for 15 min.. Cbz-CI (60.7 mL, 426 mmol) was added drop wise and stirred for 1h. The reaction mixture was stirred to RT and stirred for 12 h. After completion of starting material (by TLC), diluted the reaction mass with EtOAc (300 ml). The separated organic layer was washed with (2x200 ml. ) of saturated aHCO * solution followed by brine solution (2x100 mL ). The organic layer was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford crude material was triturated with -hexane (500mL) to afford 6S-Y (70 g, 74 percent) as white solid. H-NMR: (400 MHz, DMSO-d6): δ 7.37-7.30 (m, 5H), 7.20 (d, J = 8.4 Hz, 1H), 5.06 (s, 2H), 4.78 (d, J= 6.8 Hz, 1H), 4.09-4.05 (m, 2H), 3.64 (s, 3H), 1.09 (d, J= 6.0 Hz, 3H). LCMS m/z: 268.2[M++1] |
70 g | Stage #1: With sodium hydrogencarbonate In 1,4-dioxane; water at 0℃; for 0.25 h; Stage #2: at 0 - 20℃; for 13 h; |
To a stirring solution of 4S-H (60 g, 353 mmol) in water/1,4 dioxane (150 mL/300 mL) The reaction mixture was cooled to 0 °C added NaHCO3 (88.9 g, 1.059 mol) at 0 C and stirred for 1 min. Cbz-Cl (60.7 mL. 426 mmol) was added drop wise and stirred for 1 h. The reaction mixture was stirred to RT and stirred for 12 h. After completion of starting material (by TLC), diluted the reaction mass with EtOAc (300 ml). The separated organic layer was washed with (2x200 mL) of saturated NaHCO3 solution followed by brine solution (2x100 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material was triturated with n-hexane (500mL) to afford 4S-I (70 g, 74 percent) as white solid. 1H-NMR: (400 MHz, DMSO-d6): δ 7.37-7.30 (m, 5H), 7.20 (d, J = 8.4 Hz, 1H), 5.06 (s, 2H), 4.78 (d, J= 6.8 Hz, 1H), 4.09-4.05 (m, 2H), 3.64 (s, 3H), 1.09 (d, J= 6.0 Hz, 3H). LCMS m/z: 268.2[M++1] |
105 kg | With sodium carbonate In methanolLarge scale | Plus 99. 5percent of the 125 kg of methanol,A saturated solution of sodium carbonate was added dropwise,Adjusting the pH of the solution to 7-8;50 kg of benzyl chloroformate was added dropwise,Reaction 3-5h, filtration,To give 105 kg of β-hydroxy N-formyl benzyl ester threonine methyl ester |
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