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.. SDS of cas: 1159408-65-7
The general reactant of this compound is N-(Benzyloxycarbonyl)-6-aminohexanoic acid；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), Reagents is Diisopropylethylamine，1-[Bis(dimethylamino)methylene]-1H-benzotriazolium hexafluorophosphate(1-) 3-oxide, Catalyst(), Solvent is Dimethylformamide, Products 12-Oxa-2,9,16,20-tetraazapentacosanoic acid, 8,15,21-trioxo-10,10-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]-25-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl]oxy]-, phenylmethyl ester, Yield: 58%, Synthetic Methods procedure :1. Mix the reactant ( 0.333 g, 1.257 mmol ) in DMF ( 30 mL ) with HBTU ( 0.524 g, 1.38 mmol ) and DIEA ( 0.450 mL, 2.5 mmol ) , stir for 5 minutes., 2. Add a solution of the amine ( 1.60 g, 0.838 mmol ) in DMF ( 5 mL ) and stir the mixture overnight at room temperature., 3. Remove the solvents and volatiles under reduced pressure, dissolve the residue in DCM., 4. Purify the crude product by silica gel chromatography using EtOAc and 5-20% MeOH in DCM as eluents., , Transfornation (Acylation of Nitrogen Nucleophiles by Carboxylic Acids. Characterization Data include ‘s Proton NMR Spectrum : ( 500 MHz, DMSO-d 6 ) : δ 7.90-7.79 ( m, 6H, NH ) ; 7.74 ( t, J = 5.5 Hz, 3H, NH ) ; 7.37-7.26 ( m, 5H ) ; 7.20 ( t, J = 5.6 Hz, 1H, NH ) ; 6.98 ( s, 1H, NH ) , 5.20 ( d, J = 3.4 Hz, 3H, sugar H4 ) ; 4.98 ( s, 2H ) ; 4.95 ( dd, J = 3.4, 11.2 Hz, 3H, sugar H3 ) ; 4.48 ( d, J = 8.4 Hz, 3H, sugar H1 ) ; 4.07-3.95 ( m, 9H, sugar H5, H6, H6′ ) ; 3.86 ( dt, J = 8.8, 11.0 Hz, 3H, sugar H2 ) ; 3.69 ( dt, J = 6.0, 9.9 Hz, 3H ) ; 3.55-3.47 ( m, 12H ) ; 3.43-3.33 ( m, 3H ) ; 3.06-2.98 ( m, 12H ) ; 2.95 ( q, J = 6.8 Hz, 2H ) ; 2.27 ( t, J = 6.4 Hz, 6H ) ; 2.09 ( s, 9H ) ; 2.03 ( t, J = 7.1 Hz, 8H ) ; 1.98 ( s, 9H ) ; 1.89 ( s, 9H ) ; 1.76 ( s, 9H ) ; 1.54-1.33 ( m, 20H ) ; 1.28-1.16 ( m, 4H ) ., Carbon-13 NMR : ( 126 MHz, DMSO-d 6 ) : δ 172.4, 172.0, 170.1, 170.0, 169.9, 169.6, 169.4, 156.1, 137.3, 128.3, 127.8, 127.7, 101.0, 70.5, 69.8, 68.7, 68.3, 67.3, 66.7, 65.1, 61.4, 59.5, 53.2, 49.4, 41.6, 40.2, 36.4, 36.3, 36.0, 35.8, 35.0, 29.3, 29.2, 28.6, 25.9, 25.0, 22.8, 21.8, 20.5, 20.4., Mass Spectrum: Mass calc. for C93H145N11O39: 2039.97; found: 2062.90 ( M+Na, MALDI-TOF, matrix: HABA ) ., State is white foamy solid
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Reference:
CAS Method Number 3-353-CAS-9716164,
,CAS Method Number 3-367-CAS-11845945