Today I’d like to introduce a new chemical compound, CAS is 1159408-65-7, Name is 4,8-Dioxa-12,16-diazaheneicosanamide, 6-amino-11,17-dioxo-6-[[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]-N-[3-[[1-oxo-5-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl]oxy]pentyl]amino]propyl]-21-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl]oxy]-, 2,2,2-trifluoroacetate, Formula is C81H129F3N10O38, Molecular Weight is 1907.93g/mol. Because of its complex structure and huge molecular weight, this compound is rarely understood. Now let me introduce some knowledge about its synthesis.. Quality Control of 1159408-65-7
The general reactant of this compound is Phenylmethyl 8,14-dioxo-3,3-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]-18-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl]oxy]-5-oxa-2,9,13-triazaoctadecanoate；Trifluoroacetic acid, Reagents is Acetic acid；Hydrogen, Catalyst(Palladium), Solvent is Methanol,Dichloromethane,Toluene, Products 4,8-Dioxa-12,16-diazaheneicosanamide, 6-amino-11,17-dioxo-6-[[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]-N-[3-[[1-oxo-5-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl]oxy]pentyl]amino]propyl]-21-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl]oxy]-, 2,2,2-trifluoroacetate (1:1), Yield: 98%, Synthetic Methods procedure :1. Dissolve the reactant ( 56 g, 29 mmol ) in MeOH ( 300 mL ) and purge with argon., 2. Add 10 wt% Pd-C ( 5 g, wet Degussa type E101 NE/W ) and acetic acid ( 2.3 mL ) , and hydrogenate the reaction under normal pressure overnight., 3. Filter the reaction mixture through celite and evaporate the filtrate under reduced pressure., 4. Dissolve the residue in DCM/toluene ( 5:1, v/v ) , add trifluoroacetic acid ( TFA, 2.3 mL ) and stir the mixture for 30 minutes at room temperature., 5. Remove the solvents under reduced pressure., Transfornation (Hydrolysis or Hydrogenolysis of Amides/ Imides/ Carbamates. Characterization Data include ‘s Proton NMR Spectrum : ( 400 MHz, DMSO-d 6 ) : δ 8.06 ( brs, 3H, -NH3 + ) ; 7.88 ( t, J = 5.5 Hz, 3H, NH ) ; 7.82 ( d, J = 9.2 Hz, 3H, NH ) ; 7.76 ( t, J = 5.6 Hz, 3H, NH ) ; 5.20 ( d, J = 3.4 Hz, 3H, sugar H4 ) ; 4.95 ( dd, J = 3.4, 11.2 Hz, 3H, sugar H3 ) ; 4.47 ( d, J = 8.5 Hz, 3H, sugar H1 ) ; 4.07 – 3.97 ( m, 9H, sugar H5, H6, H6′ ) ; 3.86 ( dt, J = 8.9, 11.0 Hz, 3H, sugar H 2 ) ; 3.69 ( dt, J = 5.9, 9.8 Hz, 3H ) ; 3.63 ( t, J = 6.3 Hz, 6H ) ; 3.48-3.34 ( m, 9H ) ; 3.03 ( quintet, J = 6.6 Hz, 12H ) ; 2.33 ( t, J = 6.2 Hz, 6H ) ; 2.09 ( s, 9H ) ; 2.03 ( t, J = 7.1 Hz, 6H ) ; 1.99 ( s, 9H ) ; 1.89 ( s, 9H ) ; 1.76 ( s, 9H ) ; 1.56-1.38 ( m, 18H ) ., Carbon-13 NMR : ( 101 MHz, DMSO-d 6 ) : δ 172.0, 170.0, 169.9, 169.5, 169.3, 158.4, 158.1, 116.9, 114.0, 100.9, 70.4, 69.8, 68.6, 68.1, 67.6, 66.6, 61.3, 59.1, 49.3, 36.3, 36.2, 35.7, 35.0, 29.2, 28.5, 22.6, 21.8, 20.4, 20.3., Mass Spectrum: Mass calc. for free base C79H128N10O36: 1792.84; found: 1815.83 ( M+Na+, MALDI-TOF, matrix: HABA ) ., State is offwhite solid
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Reference:
CAS Method Number 3-353-CAS-9716164,
,CAS Method Number 3-367-CAS-11845945