Today I’d like to introduce a new chemical compound, CAS is 1159408-72-6, HPLC 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 (3R,5S)-5-[[Bis(4-methoxyphenyl)phenylmethoxy]methyl]-3-pyrrolidinol, 12,19,25-Trioxo-14,14-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]-29-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl]oxy]-16-oxa-13,20,24-triazanonacosanoic acid, Reagents is Diisopropylethylamine, 1-[Bis(dimethylamino)methylene]-1H-benzotriazolium hexafluorophosphate(1-) 3-oxide, Catalyst(), Solvent is Dichloromethane, Products (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, Yield: 73%, Synthetic Methods procedure :1. Add HBTU ( 2.10 g, 5.55 mmol ) and DIEA ( 3 mL, 17 mmol ) to a solution of the acid ( 10.13 g, 5.05 mmol ) and amine ( 2.32 g, 5.55 mmol ) in DCM ( 100 mL ) ., 2. Stir the mixture for 2 hours at room temperature., 3. Dilute the reaction mixture with DCM and wash with water., 4. Purify the crude product by silica gel chromatography ( eluent: 3-15 % MeOH in DCM containing 0.1% Et3N ) ., Acylation of Nitrogen Nucleophiles by Carboxylic Acids, Transfornation (Acylation of Nitrogen Nucleophiles by Carboxylic Acids. Characterization Data include ‘s Proton NMR Spectrum : ( 400 MHz, DMSO-d 6, mixture of rotamers: ~0.7 ( major ) , ~0.3 ( minor ) ) : δ7.87-7.79 ( m, 6H, NH ) , 7.73 ( t, J = 5.6 Hz, 3H, NH ) ; 7.34-7.24 ( m, 4H ) ; 7.24-7.14 ( m, 5H ) ; 6.97 ( s, 1H, NH ) ; 6.90-6.82 ( m, 4H ) ; 5.20 ( d, J = 3.4, 3H, sugar H4 ) ; 4.99-4.93 ( m, 3.7H ) ; 4.88 ( d, J = 4.2, 0.3H, OH ) ; 4.48 ( d, J = 8.4, 3H, sugar H1 ) ; 4.42-4.34 ( m, 0.7H ) ; 4.32-4.24 ( m, 0.3H ) ; 4.17-4.07 ( m, 1H ) ; 4.05-3.97 ( m, 9H, sugar H5, H6, H6′ ) ; 3.86 ( dt, J = 8.8, 10.9 Hz, 3H, sugar H2 ) ; 3.72 ( s, 6H ) ; 3.69 ( dt, J = 5.4, 9.8 Hz, 3H ) ; 3.62-3.44 ( m, 13H ) ; 3.39 ( dt, J = 6.4, 9.9 Hz, 3H ) ; 3.35-3.28 ( m, 0.7H ) ; 3.27-3.21 ( m, 0.3H ) ; 3.18-3.12 ( m, 1H ) ; 3.11-2.93 ( m, 13H ) ; 2.27 ( t, J = 6.2, 6H ) ; 2.19 ( t, J = 7.5, 1.7H ) ; 2.09 ( s, 9H ) ; 2.03 ( t, J = 7.3, 8.3H ) ; 1.98 ( s, 9H ) ; 1.96-1.80 ( m, 2H ) ; 1.89 ( s, 9H ) ; 1.76 ( s, 9H ) ; 1.55-1.37 ( m, 22H ) ; 1.12-1.30 ( m, 12H ) ., Carbon-13 NMR : ( 101 MHz, DMSO-d 6 ) : δ 172.5, 172.0, 171.6, 171.2, 171.1, 171.0, 170.1, 170.00; 169.9; 169.6, 169.4, 158.1, 158.0, 157.8, 148.4, 145.1, 144.8, 140.2, 135.9, 135.8, 135.5, 135.4, 129.6, 128.9, 127.9, 127.8, 127.7, 127.6, 127.4, 126.6, 126.4, 113.2, 113.1, 112.7, 101.0, 85.8, 85.1, 79.9, 70.5, 69.8, 68.7, 68.3, 67.3, 66.7, 63.4, 62.1, 61.4, 59.5, 57.6, 55.2, 55.1, 55.0, 55.0, 54.9, 49.4, 36.4, 36.3, 36.0, 35.9, 35.1, 34.3, 29.3, 29.0, 28.6, 28.6, 25.3, 24.5, 24.5, 22.8, 21.9, 20.5, 20.4., Mass Spectrum: Mass calc. for C117H175N11O42 2406.19; found 2429.18 ( M+Na+, MALDI-TOF, matrix: HABA ) ., State is white solid
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Reference:
CAS Method Number 3-355-CAS-9994399,
,CAS Method Number 3-010-CAS-8275923