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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: Z-Ser(Bzl)-OH
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 20806-43-3 |
Formula : | C18H19NO5 |
M.W : | 329.35 |
SMILES Code : | O=C(O)[C@H](COCC1=CC=CC=C1)NC(OCC2=CC=CC=C2)=O |
Synonyms : |
Z-Ser(Bzl)-OH
|
MDL No. : | MFCD00022029 |
InChI Key : | CYYRLHUAMWRBHC-INIZCTEOSA-N |
Pubchem ID : | 6993425 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
* 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 |
---|---|---|
95% | With sodium carbonate; In 1,4-dioxane; water; | To a stirred solution of O-benzyl-L-serine (25.0 g, 128 mmole) in water (200 ml) and dioxane (100 ml) was added sodium carbonate (7.46 g, 70 mmole) at room temperature. A solution of dibenzyldicarbonate (36.1 g, 126 mmole) in dioxane (100 ml) was added dropwise and the mixture stirred for 18 hours. Dioxane was evaporated under vacuum and the aqueous residue extracted with diethyl ether. Evaporation of the dried (Na2 SO4) extracts under vacuum gave a white solid which was washed with hexane to yield crude N-benzyloxycarbonyl-O-benzyl-L-serine (39.57 g, 95%). |
95% | With sodium carbonate; In 1,4-dioxane; water; | To a stirred solution of O-benzyl-L-serine (25.0 g, 128 mmole) in water (200 ml) and dioxane (100 ml) was added sodium carbonate (7.46 g, 70 mmole) at room temperature. A solution of dibenzyldicarbonate (36.1 g, 126 mmole) in dioxane (100 ml) was added dropwise and the mixture stirred for 18 hours. Dioxane was evaporated under vacuum and the aqueous residue extracted with diethyl ether. Evaporation of the dried (Na2SO4) extracts under vacuum gave a white solid which was washed with hexane to yield crude N-benzyloxycarbonyl-O-benzyl-L-serine (39.57 g, 95%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 2C33H37N*H2O7S2; water; at 80℃; for 9h; | General procedure: [0069] As shown in the following Table 5, by using 1 mmol of optically active carboxylic acid esters, each of whichproduced an optically active carboxylic acid, a hydrolysis reaction of a carboxylic acid ester was performed. That is, 1mmol of the carboxylic acid ester and 4 mL of water were added to the ammonium pyrosulfate catalyst (5 mol%) obtainedin Example 1(1), and the mixture was heated at 80C for 9 to 20 hours while stirring was performed. The reaction mixturethus obtained was diluted with water and was then extracted with ethyl acetate. After organic layers were collected anddried with sodium sulfate, a crude product obtained by condensation under reduced pressure was purified by a columnchromatography, so that an optically active carboxylic acid was obtained. In addition, the optical purity of the reactionproduct was measured by a chiral HPLC. Characteristic chemical shifts (ppm) by 1H NMR (CDCl3) and the analyticalconditions of the chiral HPLC are shown below. In addition, the results are shown in Table 5. |
The starting material is prepared as follows: A solution of 1.lg of N-carbobenzoxy-O-benzyl-(L)-serine, 0.88 g of diacetone-D-glucose, 0.74 g of 1-(3-di-methylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.41 g of 4-dimethylaminopyridine in 20 ml of methylene chloride is stirred at room temperature overnight. The mixture is concentrated, ethyl acetate is added and washed with 1N hydrochloric acid, water, saturated sodium bicarbonate, dried (Na2 SO4), filtered and concentrated. The residue is chromatographed on silica eluding with ethyl acetate-methylene chloride (1:4) to give N-carbobenzoxy-0-benzyl-(L)-serine 1,2:5,6-di-O-isopropylidene-D-glucofuranos-3-yl ester. |