Today I’d like to introduce a new chemical compound, CAS is 1159408-61-3, Name is 4-(((3R,5S)-1-(1-(((2R,3R,4R,5R,6R)-3-Acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-16,16-bis((3-((3-(5-(((2R,3R,4R,5R,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)pentanamido)propyl)amino)-3-oxopropoxy)methyl)-5,11,18-trioxo-14-oxa-6,10,17-triazanonacosan-29-oyl)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)pyrrolidin-3-yl)oxy)-4-oxobutanoic acid, Formula is C121H179N11O45, Molecular Weight is 2507.76g/mol. Because of its complex structure and huge molecular weight, this compound is rarely understood. Now let me introduce some knowledge about its synthesis.. Safety of 1159408-61-3
The general reactant of this compound is 5-[[3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl]oxy]pentanoic acid;Phenylmethyl N-[2-[3-[(3-aminopropyl)amino]-3-oxopropoxy]-1,1-bis[[3-[(3-aminopropyl)amino]-3-oxopropoxy]methyl]ethyl]carbamate, Reagents is 1-Hydroxybenzotriazole, Diisopropylethylamine;1-[Bis(dimethylamino)methylene]-1H-benzotriazolium hexafluorophosphate(1-) 3-oxide, Catalyst(), Solvent is Dimethylformamide, Products 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, Yield: 58%, Synthetic Methods procedure :1. Add HOBt ( 25.00 g, 0.16 mmol ) and HBTU ( 75.15 g, 198.15 mmol ) to a solution of triamine ( 35.0 g, 54 mmol ) and the acid ( 80.54 g, 180.10 mmol ) in DMF ( 300 mL ) ., 2. Add DIEA ( 94 mL, 544 mmol ) slowly to above mixture., 3. Stir the reaction for 3 hours at room temperature, dilute with water and extract the mixture with ether ( 300 mL ) ., 4. Separate the water phase, extract with DCM ( 2 x 500 mL ) and wash the combined organic layers consecutively with saturated NaHCO3 ( 400 mL ) , water ( 2 x 300 mL ) and brine ( 300 mL ) ., 5. Dry over anhydrous Na2SO4, evaporate the solvent under reduced pressure., 6. Purify the residue by silica gel chromatography ( eluent: 3-15 % MeOH in DCM ) ., Transfornation (Acylation of Nitrogen Nucleophiles by Carboxylic Acids. Characterization Data include ‘s Proton NMR Spectrum : ( 400 MHz, DMSO-d 6 ) : δ 7.87–7.76 ( m, 6H, NH ) ; 7.71 ( t, J = 5.7 Hz, 3H, NH ) ; 7.37-7.25 ( m, 5H ) ; 6.52 ( brs, 1H, NH ) ; 5.20 ( d, J = 3.4 Hz, 3H, sugar H4 ) ; 5.00–4.92 ( m, 5H ) ; 4.47 ( d, J = 8.5 Hz, 3H, sugar H1 ) ; 4.06–3.97 ( m, 9H, sugar H5, H6, H6′ ) ; 3.86 ( dt, J = 8.8, 11.1 Hz, 3H, sugar H2 ) ; 3.69 ( dt, J = 5.6, 9.9 Hz, 3H ) ; 3.53 ( t, J = 6.4 Hz, 6H ) ; 3.47 ( s broad, 6H ) ; 3.39 ( dt, J = 6.4, 9.9 Hz, 3H ) ; 3.07-2.97 ( m, 12H ) ; 2.26 ( t, J = 6.4 Hz, 6H ) ; 2.09 ( s, 9H ) ; 2.03 ( t, J = 7.0 Hz, 6H ) ; 1.98 ( s, 9H ) ; 1.88 ( s, 9H ) ; 1.76 ( s, 9H ) ; 1.58–1.35 ( m, 18H ) ., Carbon-13 NMR : ( 126 MHz, DMSO-d 6 ) : δ171.9, 170.0, 169.9, 169.9, 169.6, 169.4, 137.2, 128.3, 127.7, 127.5, 101.0, 79.2, 70.5, 69.8, 68.7, 68.2, 67.3, 66.7, 61.4, 58.8, 49.4, 36.4, 36.3, 36.1, 35.0, 29.3, 28.6, 22.8, 21.8, 20.5, 20.5, 20.4., Mass Spectrum: Mass calc. for C87H134N10O38: 1926.88; found: 1949.89 [M+Na+, MALDI-TOF, matrix: 2- ( 4-hydroxyphenylazo ) benzoic acid ( HABA ) ]., State is pale yellow solid
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Reference:
CAS Reaction Number: 31-355-CAS-9994399,
,CAS Method Number: 3-614-CAS-3165786