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[ CAS No. 756525-90-3 ] {[proInfo.proName]}

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Chemical Structure| 756525-90-3
Chemical Structure| 756525-90-3
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Product Details of [ 756525-90-3 ]

CAS No. :756525-90-3 MDL No. :MFCD13184969
Formula : C22H39NO12 Boiling Point : -
Linear Structure Formula :- InChI Key :IBZNTYBFTKFSMU-UHFFFAOYSA-N
M.W : 509.54 Pubchem ID :51340981
Synonyms :

Safety of [ 756525-90-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 756525-90-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 756525-90-3 ]

[ 756525-90-3 ] Synthesis Path-Downstream   1~22

  • 1
  • C53H69N11O18S2 [ No CAS ]
  • [ 756525-90-3 ]
  • C71H103N11O27S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
11.6% With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; for 48h; chemoselective reaction;
  • 2
  • [ 756525-90-3 ]
  • [ 991-01-5 ]
  • isodesmosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In aq. phosphate buffer at 40℃; for 0.333333h;
  • 3
  • [ 756525-90-3 ]
  • [ 1110-20-9 ]
  • desmosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In aq. phosphate buffer at 40℃; for 0.333333h;
  • 4
  • [ 756525-90-3 ]
  • (S)-N1-(2-(1,4-diazepan-1-yl)ethyl)-N3-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)-N1-methylisophthalamide [ No CAS ]
  • (S)-N1-(2-(4-(2,5,8,11,14,17,20,23-octaoxahexacosan-26-oyl)-1,4-diazepan-1-yl)ethyl)-N3-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)-N1-methylisophthalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With triethylamine In N,N-dimethyl-formamide at 60℃; for 1h; 197 (S)-N1-(2-(4-(2,5,8,11,14,17,20,23-octaoxahexacosan-26-oyl)-1,4-diazepan-1-yl)ethyl)-N3-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)-N1-methylisophthalamide To a mixture of (S)-N1-(2-(1,4-diazepan-1-yl)ethyl)-N3-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)-N1-methylisophthalamide (0.024, 20 mg) and m-dPEG8-NHS ester (0.024 mmol, 12.2 mg) in DMF (0.15 mL) was added triethylamine (0.144 mmol, 14.6 mg). The mixture was stirred at 60° C. for 1 h and purified by prep. HPLC to give a brown gel (6.3 mg, 18%). MS (ES, m/z): 1096.55 [M+H]+.
  • 5
  • [ 756525-90-3 ]
  • C57H92N14O22 [ No CAS ]
  • C75H126N14O31 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% In aq. phosphate buffer; acetonitrile at 20℃; for 2h; 37 Synthesis of Compound (C-7) Compound a (10mg, 7.5μmol) and 100mM phosphate buffer pH 7.4 (1 ml), was dissolved in acetonitrile (0.5 ml), compound 9 (5.7mg, 11μmol) was added and stirred for 2 hours at room temperature . Reverse phase column chromatography (column: Inertsil ODS-3 5μm 10x250mm, Mobile phase A: 0.05% TFA aqueous solution, mobile phase B: 0.05% TFA in acetonitrile, flow rate 6.0 ml / min) to give frozen compound by drying (C-7) (6.5mg, 50%) was obtained.
  • 6
  • [ 756525-90-3 ]
  • C45H52N8O5 [ No CAS ]
  • 3,13-dimethoxycarbonyl-2,12-bis[3,5-bis(2-aza-6,9,12,15,18,-21,24,27-octaoxa-3-oxooctacosan-1-yl)phenyl]-5-methoxy-8,8,18,18-tetramethylbacteriochlorin [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With caesium carbonate In N,N-dimethyl-formamide for 2.5h; Inert atmosphere;
  • 7
  • [ 756525-90-3 ]
  • C37H41N5O4 [ No CAS ]
  • 13-[2-(4-carboxyphenyl)ethyl]-5-methoxy-8,8,18,18-tetramethyl-3-(4-aza-8,11,14,17,20,23,26,29-octaoxa-5-oxotriacontan-1-yl)-7-oxobacteriochlorin [ No CAS ]
YieldReaction ConditionsOperation in experiment
5 mg With caesium carbonate In N,N-dimethyl-formamide for 2.5h; Inert atmosphere;
  • 8
  • [ 756525-90-3 ]
  • C54H60N8O7 [ No CAS ]
  • 15-[4-(3-carboxyethyl)phenyl]-3,13-dimethoxycarbonyl-2,12-bis[3,5-bis(2-aza-6,9,12,15,18,21,24,27-octaoxa-3-oxooctacosan-1-yl)phenyl]-5-methoxy-8,8,18,18-tetramethylbacteriochlorin [ No CAS ]
YieldReaction ConditionsOperation in experiment
12 mg With caesium carbonate In N,N-dimethyl-formamide for 2.5h; Inert atmosphere;
  • 9
  • [ 756525-90-3 ]
  • C49H55N9O7 [ No CAS ]
  • 2,12-bis[3,5-bis(2-aza-6,9,12,15,18,21,24,27-octaoxa-3-oxooctacosan-1-yl)phenyl]-152-N-(3-carboxypropyl)-3-methoxycarbonyl-5-methoxy-8,8,18,18-tetramethylbacteriochlorin-13,15-dicarboimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
5 mg With caesium carbonate In N,N-dimethyl-formamide for 2.5h; Inert atmosphere;
  • 10
  • 3,6-diamino-N<SUP>2</SUP>,N<SUP>5</SUP>-bis(2-aminoethyl)pyrazine-2,5-dicarboxamide bis-trifluoroacetic acid [ No CAS ]
  • [ 756525-90-3 ]
  • [ 960510-23-0 ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; 10 Example 10: 3, 6-diamino-N2,N5-bis(26-oxo-2,5, 8, 11,14, 17,20, 23-octaoxa-27-azanonacosan-29- yl)p razine-2,5-dicarboxamide To a solution of Example 7 (50.3 mg, 0.10 mmol) in DMF (5 mL) was added TEA (109 mg, 1.08 mmol) and 2,5-dioxopyrrolidin-l-yl 2,5,8,11, 14, 17,20,23-octaoxahexacosan-26- oate (128 mg, 0.25 mmol) and the reaction was stirred for 16 h at room temperature. The reaction was concentrated and the residue was purified by medium pressure reversed phase chromatography (LiChroprep RP-18 Lobar (B) 25x310 mm- EMD chemicals 40-63 μιη, -70 g, 90/10 to 80/20 0.1% TFA-ACN) to afford 87.9 mg (82% yield) of Example 10 as an orange film: lNMR (300 MHz, DMSO-d6) δ 8.46 (t, J=5.7 Hz, 2H), 7.96 (t, J=5.4 Hz, 2H), 3.16-3.73 (complex m, 74 H), 2.28-2.32 (m, 2H). 13C NMR (75 MHz, DMSO-d6) multiple conformations, δ 170.1 (s), 169.9 (s) 169.8 (s), 165.1 (s), 146.0 (s), 126.2 (s). 71.2 (t), 69.7 (t), 69.6 (t), 69.5 (t), 66.7 (t), 58.0 (q), 38.2 (t), 36.2 (t). LCMS (15-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=5.90 min on 250 mm column, (M+H)+=l 071, (M+2H)2+=536. UV/vis (100 μΜ in PBS) Xabs =438 nm. Fluorescence (100 nM) nm, Xem =560 nm.
82% With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; 8 3,6-diamino-N2,N5-bis(26-oxo-2,5,8,11,14,17,20,23-octaoxa-27-azanonacosan-29-yl)pyrazine-2,5-dicarboxamide To a solution of Example 5 (50.3 mg, 0.10 mmol) in DMF (5 mL) was added TEA (109 mg, 1.08 mmol) and 2,5-dioxopyrrolidin-1-yl 2,5,8,11,14,17,20,23-octaoxahexacosan-26-oate (128 mg, 0.25 mmol) and the reaction was stirred for 16 h at room temperature. The reaction was concentrated and the residue was purified by medium pressure revered phase chromatography (LiChroprep RP-18 Lobar (B) 25*310 mm-EMD chemicals 40-63 μm, ˜70 g, 90/10 to 80/20 0.1% TFA-ACN) to afford 87.9 mg (82% yield) of example 8 as an orange film: 1NMR (300 MHz, DMSO-d6) δ 8.46 (t, J=5.7 Hz, 2H), 7.96 (t, J=5.4 Hz, 2H), 3.16-3.73 (complex m, 74H), 2.28-2.32 (m, 2H). 13C NMR (75 MHz, DMSO-d6)-multiple conformations-δ 170.1 (s), 169.9 (s) 169.8 (s), 165.1 (s), 146.0 (s), 126.2 (s).71.2 (t), 69.7 (t), 69.6 (t), 69.5 (t), 66.7 (t), 58.0 (q), 38.2 (t), 36.2 (t). LCMS (15-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=5.90 min on 250 mm column, (M+H)+=1071, (M+2H)2+=536. UV/vis (100 μM in PBS) λabs=438 nm. Fluorescence (100 nM) λex=438 nm, λem=560 nm.
82% With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; 8 3,6-Diamino-N2,N5-bis(26-oxo-2,5,8,11,14,17,20,23-octaoxa-27-azanonacosan-29-yl)pyrazine-2,5-dicarboxamide To a solution of Example 50 5 (50.3 mg, 0.10 mmol) in 7 DMF (5 mL) was added 22 TEA (109 mg, 1.08 mmol) and 71 2,5-dioxopyrrolidin-1-yl 2,5,8,11,14,17,20,23-octaoxahexacosan-26-oate (128 mg, 0.25 mmol) and the reaction was stirred for 16 h at room temperature. The reaction was concentrated and the residue was purified by medium pressure revered phase chromatography (LiChroprep RP-18 Lobar (B) 25×310 mm-EMD chemicals 40-63 μm, 70 g, 90/10 to 80/20 0.1% 67 TFA-ACN) to afford 87.9 mg (82% yield) of example 8 as an orange film: 1NMR (300 MHz, DMSO-d6) δ 8.46 (t, J=5.7 Hz, 2H), 7.96 (t, J=5.4 Hz, 2H), 3.16-3.73 (complex m, 74H), 2.28-2.32 (m, 2H). 13C NMR (75 MHz, DMSO-d6)-multiple conformations-□ 170.1 (s), 169.9 (s) 169.8 (s), 165.1 (s), 146.0 (s), 126.2 (s). 71.2 (t), 69.7 (t), 69.6 (t), 69.5 (t), 66.7 (t), 58.0 (q), 38.2 (t), 36.2 (t). LCMS (15-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=5.90 min on 250 mm column, (M+H)+=1071, (M+2H)2+=536. UV/vis (100 □M in PBS) □abs=438 nm. Fluorescence (100 nM) □ex=438 nm, □em=560 nm.
  • 11
  • [ 756525-90-3 ]
  • [ 105047-45-8 ]
  • (S)-32-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-26-oxo-2,5,8,11,14,17,20,23-octaoxa-27-azatritriacontan-33-oic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere; 4.1.6 (S)-20-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-14-oxo-2,5,8,11-tetraoxa-15-azahenicosan-21-oic acid (5, Fig. S6) General procedure: Fmoc-l-lysine (2.32g, 6.30mmol) was dissolved in 40mL anhydrous DCM, then methyl-PEG4-NHS (2.10g, 6.30mmol) and DIPEA (71mg, 3.94mmol) was added. The reaction was kept stirring overnight in an argon atmosphere. After adding an appropriate amount of DCM, the mixture was washed with 0.7M HCl, water, brine, and dried over anhydrous Na2SO4. The organic phase was evaporated under reduced pressure, followed by purification on a silica column with CH2Cl2/MeOH=20:1 as the eluent to obtain the pure product as a light-yellow oil (2.99g, yield: 81%). 1H NMR (400MHz, DMSO-d6) δ: 12.21 (s, 1H), 7.90 (d, J=7.6Hz, 2H), 7.84 (t, J=5.6Hz, 1H), 7.73 (d, J=7.6Hz, 2H), 7.64 (d, J=8.0Hz, 1H), 7.42 (t, J=7.6Hz, 2H), 7.33 (td, J=7.6, 1.2Hz, 2H), 4.32-4.19 (m, 3H), 3.94-3.86 (m, 1H), 3.58 (t, J=6.8Hz, 2H), 3.54-3.38 (m, 12H), 3.22 (s, 3H), 3.08-2.97 (m, 2H), 2.29 (t, J=6.4Hz, 2H), 1.74-1.54 (m, 2H), 1.45-1.25 (m, 4H). MS (ESI) m/z: 585.30 [M-H]-.
76% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere; 4.1.6 (S)-20-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-14-oxo-2,5,8,11-tetraoxa-15-azahenicosan-21-oic acid (5, Fig. S6) General procedure: Fmoc-l-lysine (2.32g, 6.30mmol) was dissolved in 40mL anhydrous DCM, then methyl-PEG4-NHS (2.10g, 6.30mmol) and DIPEA (71mg, 3.94mmol) was added. The reaction was kept stirring overnight in an argon atmosphere. After adding an appropriate amount of DCM, the mixture was washed with 0.7M HCl, water, brine, and dried over anhydrous Na2SO4. The organic phase was evaporated under reduced pressure, followed by purification on a silica column with CH2Cl2/MeOH=20:1 as the eluent to obtain the pure product as a light-yellow oil (2.99g, yield: 81%). 1H NMR (400MHz, DMSO-d6) δ: 12.21 (s, 1H), 7.90 (d, J=7.6Hz, 2H), 7.84 (t, J=5.6Hz, 1H), 7.73 (d, J=7.6Hz, 2H), 7.64 (d, J=8.0Hz, 1H), 7.42 (t, J=7.6Hz, 2H), 7.33 (td, J=7.6, 1.2Hz, 2H), 4.32-4.19 (m, 3H), 3.94-3.86 (m, 1H), 3.58 (t, J=6.8Hz, 2H), 3.54-3.38 (m, 12H), 3.22 (s, 3H), 3.08-2.97 (m, 2H), 2.29 (t, J=6.4Hz, 2H), 1.74-1.54 (m, 2H), 1.45-1.25 (m, 4H). MS (ESI) m/z: 585.30 [M-H]-.
With N-ethyl-N,N-diisopropylamine
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Intermediate 35-1 ^ (1297) N2-[(9H-Fluoren-9-yl)methoxy]carbonyl}-N6-(26-oxo-2,5,8,11,14,17,20,23- octaoxahexacosan-26-yl)-L-lysine To 1-[(26-oxo-2,5,8,11,14,17,20,23-octaoxahexacosan-26-yl)oxy]pyrrolidine-2,5-dione (CAS 756525-90-3, 500 mg, 981 µmol) in DMF 8.6 mL) was added N2-[(9H-fluoren-9- ylmethoxy)carbonyl]-L-lysine (CAS 105047-45-8, 350 mg, 1.08 mmol) and N,N- diisopropylethylamine (600 µl, 3.4 mmol) The mixture was stirred for 1 h at r.t., then diluted with formic acid (130 µl, 3.4 mmol) in DMSO (9 mL) and purified by preparative HPLC to give to give 560 mg (90% purity, 67% yield)of the title compound. (1299) HPLC: Instrument: Labomatic HD-5000, pump head HDK-280, gradient module NDB-1000, fraction collector Labomatic Labocol Vario 2000, Knauer UV detector Azura UVD 2.1S, Prepcon 5 software. Column: Chromatorex C18 10µM 120x30 mm; Eluent A: water + 0.1% fomic acid; Eluent B: acetonitrile; gradient: 0-8 min 5-60% B, 8-13 min 60% B, rate 150 mL/min, temperature 25°C. (1300) LC-MS (Method 1): Rt = 1.10 min; MS (ESIpos): m/z = 763 [M+H]+. (1301) 1H-NMR (400MHz, DMSO-d6) δ [ppm]: 1.25 - 1.43 (m, 4H), 1.53 - 1.74 (m, 2H), 2.26 - 2.32 (m, 2H), 2.98 - 3.06 (m, 2H), 3.23 (s, 3H), 3.40 - 3.44 (m, 2H), 3.44 - 3.51 (m, 26H), 3.57 (t, 2H), 3.84 - 3.95 (m, 1H), 4.19 - 4.29 (m, 3H), 7.33 (t, 2H), 7.42 (t, 2H), 7.62 (d, 1H), 7.73 (d, 2H), 7.79 - 7.85 (m, 1H), 7.90 (d, 2H).

  • 13
  • [ 756525-90-3 ]
  • 2,2’-(piperidine-4,4-diyl)diacetic acid [ No CAS ]
  • 2,2‘-(1-(2,5,8,11,14,17,20,23-octaoxahexacosan-26-oyl)piperidine-4,4-diyl)diacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-[(26-oxo-2,5,8,11,14,17,20,23-octaoxahexacosan-26-yl)oxy]pyrrolidine-2,5-dione; 2,2’-(piperidine-4,4-diyl)diacetic acid In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: With triethylamine In N,N-dimethyl-formamide at 20℃; 17.1 Step 1 2,2'-(l-(2, 5, 8, 11, 14, 17, 20, 23-octaoxahexacosan-26-oyl)piperidine-4, 4-diyl)diacetic acid To a solution of 2,2'-(piperidine-4,4-diyl)diacetic acid (250 mg, 1.242 mmol) in anhydrous DMF (20 mL) at rt was added PEG-8 NHS Ester (992 mg, 1.947 mmol, Broadpharm) portionwise over a period of 15min and then TEA (0.450 ml, 3.23 mmol). The resulting mixture was allowed to stir at rt overnight. The reaction mixture was then concentrated and the residue purified by reverse phase column chromatography on lOOg CI 8, eluting with AcCN/L^O (gradient from 5% to 40%) to give the title compound after lyophilization. UPLC-Method C: tj_ = 2.43 min, m/z = 596 (z = 1).
  • 14
  • [ 756525-90-3 ]
  • 2,2’-(piperidine-4,4-diyl)diacetic acid [ No CAS ]
  • bis(2,5-dioxopyrrolidin-1-yl) 2,2‘-(1-(2,5,8,11,14,17,20,23-octaoxahexacosan-26-oyl)piperidine-4,4-diyl)diacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 20 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
  • 15
  • [ 756525-90-3 ]
  • C106H139N19O35 [ No CAS ]
  • C124H173N19O44 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With sodium dihydrogenphosphate In tetrahydrofuran at 20℃; for 6h; 144 Example 144. Synthesis of an asymmetrically cross-linked PBD dimer C-11. C-10 compound (235.0 mg, 0.105 mmol) was dissolved in a mixture solution of THF (3 ml) and 0.1 M, NaH 2PO 4 (3 ml) , pH 7.5, followed by addition of N-succinimidyl 2, 5, 8, 11, 14, 17, 20, 23-octaoxahexacosan-26-oate (43.0 mg, 0.084 mmol) in 4 portions in 2 h. The reaction mixture was then continued to stir at RT for 4 h, and co-evaporated with DMF (10 ml) to dryness to afford the crude product C-11 which was further purified by reverse phase HPLC (250 (L) mm x 50 (d) mm, C 18 column, 20-60%acetonitrile/water in 40 min, v =8 ml/min) to afford the pure product C-11 (215.5 mg, 78%yield, 95%pure ) as a foam. ESI MS m/z: calcd for C 124H 174N 19O 44 [M+H] + 2633.20, found 2633.85.
  • 16
  • [ 756525-90-3 ]
  • C97H124N16O33 [ No CAS ]
  • C133H192N16O51 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With sodium dihydrogenphosphate In tetrahydrofuran at 20℃; for 6h;
  • 17
  • [ 756525-90-3 ]
  • C106H143N19O35 [ No CAS ]
  • C124H177N19O44 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With sodium dihydrogenphosphate In tetrahydrofuran at 20℃; for 6h;
  • 18
  • [ 756525-90-3 ]
  • (2S)-2-amino-6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-hexanoic acid hydrochloride [ No CAS ]
  • (28S)-28-[4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl]-26-oxo-2,5,8,11,14,17,20,23-octaoxa-27-azanonacosan-29-oic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With pyridine; N-ethyl-N,N-diisopropylamine at 20℃; for 0.5h; 38E.1 Step 1: (28S)-28-[4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl]-26-oxo-2,5,8,11,14,17,20,23- octaoxa-27-azanonacosan-29-oic acid To a mixture of (2S)-2-amino-6-(2,5-dioxopyrrol-1-yl)hexanoic acid hydrochloride (1.05 g, 4.00 mmol) and 1-[(26-oxo-2,5,8,11,14,17,20,23-octaoxahexacosan-26-yl)oxy]pyrrolidine-2,5-dione (2.08 g, 4.04 mmol) in pyridine (21.0 mL) was added DIEA (1.43 mL, 8.20 mmol) and the mixture was allowed to stir at rt for 30 mins then cooled to 0 oC and stirred overnight. The volatile solvent was removed and the residue was azeotroped with toluene (3×20 mL) and acetonitrile (10 mL) to give (28S)-28-[4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl]-26-oxo- 2,5,8,11,14,17,20,23-octaoxa-27-azanonacosan-29-oic acid (4.00 g, 100% yield) as a colorless oil. LCMS (AA): m/z = 619.3 (M-H).
  • 19
  • [ 756525-90-3 ]
  • [ 76387-70-7 ]
  • (29S)-29-[(tert-butoxycarbonyl)amino]-26-oxo-2,5,8,11,14,17,20,23-octaoxa-27-azatriacontan-30-oic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; 36.1 Step 1: (19S)-19-[4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl]-17-oxo-2,5,8,11,14-pentaoxa- 18-azaicosan-20-oic acid General procedure: To a solution of 1-[(17-oxo-2,5,8,11,14-pentaoxaheptadecan-17-yl)oxy]pyrrolidine- 2,5-dione (4.0 g, 10.5 mmol) in anhydrous DCM (10 mL) was added (S)-2-amino-6-(2,5-dioxo- 2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid hydrochloride (3.4 g, 12.9 mmol) dissolved in DMF (40 mL) followed by N,N-diisopropylethylamine (6.9 mL, 42 mmol). The reaction mixture was allowed to stir at rt for 18 h. The reaction mixture was filtered and concentrated to dryness. The crude residue was purified by preparative HPLC to afford (19S)-19-[4-(2,5-dioxo-2,5-dihydro- 1H-pyrrol-1-yl)butyl]-17-oxo-2,5,8,11,14-pentaoxa-18-azaicosan-20-oic acid (1.26 g, 24%). LCMS (AA): m/z = 489.3 (M+H).
  • 20
  • [ 756525-90-3 ]
  • [ 76387-70-7 ]
  • tert-butyl {(29S)-30-[(2,5-dioxopyrrolidin-1-yl)oxy]-26,30-dioxo-2,5,8,11,14,17,20,23-octaoxa-27-azatriacontan-29-yl}carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C 2: dicyclohexyl-carbodiimide / dichloromethane / 16 h / 20 °C
  • 21
  • [ 756525-90-3 ]
  • N-{(2S)-6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-1-[(2,5-dioxopyrrolidin-1-yl)oxy]-1-oxohexan-2-yl}-2,5,8,11,14,17,20,23-octaoxahexacosan-26-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine; N-ethyl-N,N-diisopropylamine / 0.5 h / 20 °C 2: dicyclohexyl-carbodiimide / dichloromethane / 16 h / 20 °C
  • 22
  • [ 756525-90-3 ]
  • tert-butyl (S)-(2-((5-amino-6-((2-(1-(4-((6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)methyl)benzyl)piperidin-4-yl)ethyl)amino)-6-oxohexyl)amino)-2-oxoethoxy)carbamate [ No CAS ]
  • (S)-2-PEG8-N-(2-(1-(4-((6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)methyl)benzyl)piperidin-4-yl)ethyl)-6-(2-(aminooxy)acetamido)hexanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: 1-[(26-oxo-2,5,8,11,14,17,20,23-octaoxahexacosan-26-yl)oxy]pyrrolidine-2,5-dione; tert-butyl (S)-(2-((5-amino-6-((2-(1-(4-((6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)methyl)benzyl)piperidin-4-yl)ethyl)amino)-6-oxohexyl)amino)-2-oxoethoxy)carbamate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 0.166667h; Stage #2: With trifluoroacetic acid In dichloromethane for 0.166667h; 3 (S)-Nl-(l-((2-(l-(4-((6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9- yl)methyl)benzyl)piperidin-4-yl)ethyl)amino)-6-(2-(aminooxy)acetamido)-l-oxohexan-2-yl)-N5-(PEG48)-glutaramide (251): To a solution of compound 250 (10 mg, 0.009 mmol) and PEG48-NHCO-(CH2)3-TFP ester (22 mg, 0.009 mmol) in DMF (0.5 mL) was added DIEA (12 pL, 0.069 mmol) at 23 °C. After 10 min, the solvent was removed in vacuo. To the residue was added DCM (1 mL) and TFA (1 mL). After 10 min, LCMS showed the deprotection reaction was completed. The solvent was removed in vacuo. The residue was purified by Prep-LC to obtain target compound 251 (19 mg, 0.006 mmol, 62%). MS m/z 1449 (M+2H)+.
66% Stage #1: 1-[(26-oxo-2,5,8,11,14,17,20,23-octaoxahexacosan-26-yl)oxy]pyrrolidine-2,5-dione; tert-butyl (S)-(2-((5-amino-6-((2-(1-(4-((6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)methyl)benzyl)piperidin-4-yl)ethyl)amino)-6-oxohexyl)amino)-2-oxoethoxy)carbamate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 0.166667h; Stage #2: With trifluoroacetic acid In dichloromethane for 0.166667h; 3 (S)-Nl-(l-((2-(l-(4-((6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9- yl)methyl)benzyl)piperidin-4-yl)ethyl)amino)-6-(2-(aminooxy)acetamido)-l-oxohexan-2-yl)-N5-(PEG48)-glutaramide (251): To a solution of compound 250 (10 mg, 0.009 mmol) and PEG48-NHCO-(CH2)3-TFP ester (22 mg, 0.009 mmol) in DMF (0.5 mL) was added DIEA (12 pL, 0.069 mmol) at 23 °C. After 10 min, the solvent was removed in vacuo. To the residue was added DCM (1 mL) and TFA (1 mL). After 10 min, LCMS showed the deprotection reaction was completed. The solvent was removed in vacuo. The residue was purified by Prep-LC to obtain target compound 251 (19 mg, 0.006 mmol, 62%). MS m/z 1449 (M+2H)+.
Same Skeleton Products
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