Today I’d like to introduce a new chemical compound, CAS is 1159408-72-6, COA of Formula: 1159408-72-6, Name is (2S,4R)-2-[[Bis(4-methoxyphenyl)phenylmethoxy]methyl]-4-hydroxy-λ-oxo-N-[2-[3-oxo-3-[[3-[[1-oxo-5-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl]oxy]pentyl]amino]propyl]amino]propoxy]-1,1-bis[[3-oxo-3-[[3-[[1-oxo-5-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl]oxy]pentyl]amino]propyl]amino]propoxy]methyl]ethyl]-1-pyrrolidinedodecanamide, Formula is C117H175N11O42, Molecular Weight is 2407.69g/mol. Because of its complex structure and huge molecular weight, this compound is rarely understood. Now let me introduce some knowledge about its synthesis.
The general reactant of this compound is β-D-Galactopyranoside, 5-hexen-1-yl 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate, Reagents is Sodium periodate, Catalyst(Ruthenium dichloride), Solvent is Acetonitrile,Dichloromethane,Water, Products 5-[[3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl]oxy]pentanoic acid, Yield: 71%, Synthetic Methods procedure :1. Add 4.0 mol equiv. of sodium ( meta ) periodate ( 1375 g ) in water ( 3300 mL ) to a solution of reactant ( 687 g, 1.59 mol ) in DCM and MeCN ( 4000 mL 1:1 ) ., 2. Cool the mixture to 10 °C in a cold water bath and stir for 15 minutes., 3. Add ruthenium chloride ( 5.64 g, 0.027 mol ) to the cold reaction mixture, while maintaining the temperature at or below 35 °C by external cooling over the water bath., 4. Stir the reaction mixture at room temperature for 1 hour; add an additional 1 mol equiv. of sodium ( meta ) periodate ( 343 g ) and continue stirring for 1 hour at room temperature., 5. Confirm the completion of the reaction by TLC., 6. Dilute the reaction mixture with water ( 2 L ) and adjust the pH to 7.5 by adding solid NaHCO3., 7. Remove the DCM layer, wash the aqueous layer three times with DCM ( 2 L ) and discard the organic extracts.8. Adjust the pH of aqueous layer to 3 by addition of citric acid and extract the carboxylic acid into DCM ( 3 x 4 L ) .9. Stir the organic layer with saturated brine ( 2 L ) , add 3% Na2S solution dropwise until the dark green organic phase turns to a pale yellow color.10. Separate the layers, dry the organic layer over anhydrous Na2SO4 and evaporate under reduced pressure., Transfornation (. Characterization Data include ‘s Proton NMR Spectrum : ( 400 MHz, DMSO-d 6 ) : δ 11.97 ( s, 1H, COOH ) ; 7.79 ( d, J = 9.2 Hz, 1H, NH ) ; 5.20 ( d, J = 3.4 Hz, 1H, H4 ) , 4.95 ( dd, J = 3.4, 11.2 Hz, 1H, H3 ) ; 4.48 ( d, J = 8.5 Hz, 1H, H1 ) ; 4.05-3.98 ( m, 3H, H5, H6, H6′ ) ; 3.86 ( dt, J = 8.9, 11.1 Hz, 1H, H2 ) ; 3.74-3.65 ( m, 1H, -OCH2-CH2 ) ; 3.45-3.37 ( m, 1H, -OCH2-CH2 ) ; 2.19 ( t, J = 7.0 Hz, 2H, -CH2-COOH ) ; 2.09 ( s, 3H, -COCH3 ) ; 1.99 ( s, 3H, -COCH3 ) ; 1.88 ( s, 3H, -COCH3 ) ; 1.76 ( s, 3H, -COCH3 ) ; 1.55-1.45 ( m, 4H, 2x ( -CH2 ) ) ., Carbon-13 NMR : ( 126 MHz, DMSO-d 6 ) : δ 174.4, 170.0, 169.9, 169.6, 169.3, 100.9, 70.5, 69.8, 68.4, 66.7, 61.4, 49.3, 33.2, 28.3, 22.7, 21.0, 20.5, 20.4, 20.4., HRMS: calc. for C19H29NO11: 447.1741; found 447.1743., State is offwhite solid
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Reference:
CAS Method Number 3-355-CAS-9994399,
,CAS Method Number 3-010-CAS-8275923