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CAS No. : | 1404-93-9 | MDL No. : | MFCD03613611 |
Formula : | C66H76Cl3N9O24 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 1485.71 | Pubchem ID : | - |
Synonyms : |
Vancomycin HCl(1:x)
|
Chemical Name : | (3S,6R,7R,22R,23S,26S,36R,38aR)-3-(2-Amino-2-oxoethyl)-44-[[2-O-(3-amino-2,3,6-trideoxy-3-C-methyl-α-L-lyxo-hexopyranosyl)-β-D-glucopyranosyl]oxy]-10,19-dichloro-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-[[(2R)-4-methyl-2-(methylamino)-1-oxopentyl]amino]-2,5,24,38,39-pentaoxo-22H-8,11:18,21-Dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-1H,16H-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid xhydrochloride |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
10% | The synthesis scheme for arriving at the glycopeptide derivative RV79 isdescribed below, and also provided at Figure 3. To a 40 mL vial equipped a stir bar was addedanhydrous DMF (20 mL) and DIPEA (0.20 mL). The resulting solution was heated to 65 ocon an incubated shaker and vancomycin·HCl (700 mg, 0.462 mmol) was added slowly inportions. Heating was continued until all ofvancomycin·HCl had dissolved (5-10 min). Thebeige colored solution was allowed to cool to room temperature at which point 4' -Chlorobiphenyl-4-carbaldehyde (0.1 g, 0.462 mmol) was added to the reaction mixture. The reactionmixture was allowed to stir overnight. MeOH (1.5 mL) and TFA (0.14 mL, 1.8 mmol) wereintroduced and stirring was further continued for at least 2 h. Borane tert-butylamine complex( 40 mg, 0.46 mmol) was added in portions and the reaction mixture was stirred at ambienttemperature for an additional2 h. After the reaction completed, the reaction mixture is purifiedusing reverse phase C 18 column chromatography (Phenomenex Luna 10 uM PREP C 18(2) 250x 21.2 mm column) using gradients of water and acetonitrile, each containing 0.1% ( v /v) ofTF A Fractions were evaluated using HPLC and then pertinent fractions containing RV79were pooled together for isolation of the product via lyophilization. The target compound, RV79 (81.2 mg, 0.05 mmol, 10% overall yield), was obtained as a white solid in >97% purity(by HPLC). The reaction scheme is shown at Figure 3 |