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[ CAS No. 854601-60-8 ] {[proInfo.proName]}

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Chemical Structure| 854601-60-8
Chemical Structure| 854601-60-8
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Product Details of [ 854601-60-8 ]

CAS No. :854601-60-8 MDL No. :MFCD27977521
Formula : C23H49NO11 Boiling Point : -
Linear Structure Formula :- InChI Key :SWAJVHMMXALQKJ-UHFFFAOYSA-N
M.W : 515.64 Pubchem ID :77078255
Synonyms :
Chemical Name :2,5,8,11,14,17,20,23,26,29,32-Undecaoxatetratriacontan-34-amine

Safety of [ 854601-60-8 ]

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 [ 854601-60-8 ]

* 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 [ 854601-60-8 ]

[ 854601-60-8 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 854601-60-8 ]
  • [ 4759-48-2 ]
  • [ 854601-61-9 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In benzene; at 20℃; 0.349 grams of CH3(OCH2CH2)11-NH2 (0.6789 mmoles), 0.044 grams of 1-hydroxybenzyltriazole (0.3328 mmoles), and 0.204 grams of 13-cis-retinoic acid (0.6789 mmoles) was dissolved in 10 mL of benzene. To this solution was added 0.192 g 1,3-dicyclohexylcarbodiimide (0.9318 mmoles) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered and the solvent distilled off using rotary evaporation. The product was dried under vacuum and dissolved in 20 mL dichloromethane. The solution was washed twice with 15 mL of deionized water and the organic phase dried over Na2SO4. The solution was filtered and the solvent was distilled off by rotary evaporation. To the recovered product was added 2 drops of dichloromethane containing 50 ppm butylated hydroxytoluene, and the product was dried under vacuum. Yield 0.541 g. 1H NMR (DMSO): δ 1.01 (s, 2 CH3), 1.68 (s, CH3), 3.5 (br m, PEG), 6.20 (m, 3H).
  • 2
  • [ 854601-60-8 ]
  • [ 70972-98-4 ]
  • C39H71NO11 [ No CAS ]
  • 3
  • [ 854601-60-8 ]
  • [ 1426164-23-9 ]
  • C101H187N5O46 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 1.08333h;Inert atmosphere; A solution of NH2-dPEG11-m (17.8 g, 34.5 mmol) in 50 mL of anhydrous dichloromethane was placed in a 500 mL three-neck round bottom flask equipped with a magnetic stirrer, thermocouple, balloon filled with nitrogen, and ice-methanol cooling bath. Lutidine (4.59 g, 42.8 mmol) was added to this solution, and the resulting mixture was cooled to 0[deg.] C. A solution of Phth-4-tris-TFP ester (11.11 g, 9.59 mmol) in 25 mL of anhydrous dichloromethane was added dropwise to the reaction within 45 min, stirred for an additional 20 min at 0[deg.] C., and allowed to warm to ambient temperature and stirred overnight. The reaction was monitored by TLC (Rf=0.68 for Phth-4-tris(TFP)3 and Rf=0.34 for product, in 90% DCM-10% EtOH) or HPLC, and after consumption of the TFP-ester it was quenched with cold 10% HCl (2*200 mL). The organic materials were extracted with dichloromethane (3*80 mL), the combined extracts were washed with cold 2% NaHCO3 (100 mL), and the organic phase was separated and dried over anhydrous Na2SO4. The solvent was removed on rotavap, and the obtained yellow viscous oil (26 g, ~100% pure by HPLC) was flushed by column chromatography on silica gel. The excess of side product-TFP was removed first with 50/50 mixture of CH2Cl2-EtOAc, following by gradient elution using EtOH-CH2Cl2 from 0 to 20% EtOH. Pure fractions were concentrated under reduced pressure give 11.8 g (55.8%) of clear oil. An additional 7.5 g of material was recovered from impure fractions by column chromatography on silica gel resulting in which gives total 19.3 g (91% yield) of the target compound. HPLC (3045FF acid method): RT 27.93 min, purity 100%. H NMR (400 MHz, CDCl3, [delta]): 7.85 (m, 2H, phthalimide), 7.73 (m, 2H, phthalimide), 6.92 (t, 3H, NH), 6.61 (s, 1H, NH), 3.89 (t, 2H, CH2N), 3.84-3.50 (m, 160H, CH2O), 3.49-3.40 (m, 6H, CH2O), 3.38 (s, 9H, CH3O), 2.50-2.36 (m, 10H, CH2CO). PhthN-dPEG12-tris(-dPEG11-m)3:
  • 4
  • [ 854601-60-8 ]
  • C66H78F12N2O24 [ No CAS ]
  • C117H219N5O54 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; Using m11-amine, the amine is dripped into solution of TFP ester and DIIPEA in DCM cooled to 0 C. HPLC after one hour. HPLC following morning. The r*n is washed 2*200 ml sat bicarb, 2*200 ml 10% HCL, 1*200 ml sat brine, and dried over sod sulfate. It is azeotroped 2* with 50 ml ACN after evap DCM to weigh 56 gm. This is dissolved in ACN/TBME 65 ml/475 ml and heated to ~50 C and filtered through glass fiber. The soln is cooled to ~10 C which gives an hazy mixture which is stirred overnight. The mixture oils out so the solvents are removed and the oil is dissolved in 1 to 10 oil to solvent ratio with 10% acetone-TBME. After stirring overnite it also oils but not completely but there is no solid so it is seeded with some 95% solid from a previous batch. Stirring all day does not solidify it but when the solutions is cooled to 0 C with ice the oil solidifies. This stirs overnight to give a milky solid which is diluted with 500 ml 5% acetone-TBME and then filtered. The solid is very light and comes initially through the coarse filter. It is washed with 500 ml 5% acetone/TBME and is a caramel solid with some solvent present, 35 gm (56%). HPLC (acid60 method): RT 10.12 min, purity 93%.
  • 5
  • [ 854601-60-8 ]
  • PhthN-dPEG<SUB>4</SUB>-(Tyr-OCH<SUB>2</SUB>-triazole-CH<SUB>2</SUB>CH<SUB>2</SUB>-NH-t-boc)-OH [ No CAS ]
  • PhthN-dPEG<SUB>4</SUB>-(Tyr-OCH<SUB>2</SUB>-triazole-CH<SUB>2</SUB>CH<SUB>2</SUB>-NH-t-boc)-NH-m-dPEG<SUB>11</SUB> [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 6.16667h;Inert atmosphere; A mixture of m-dPEG1 1-NH2 (1.105g, 2.143mmol), diisopropylethyl amine (0.72g, 5.57mmol) and HOBt (0.092g, 0.681 mmol) in 25mL of anhydrous dichloromethane was placed in a 100ml_ one-neck round bottom flask equipped with a magnetic stirrer, thermocouple, N2-filled balloon, and cooling ice-MeOH bath. Obtained solution was cooled to 0C, and a solution of phth-dPEG4-Tyr(0- methylene-triazole-ethane-N-BOC)acid (1.62g, 2.069mmol) in 10mL of anhydrous dichloromethane was added via syringe. The reaction stirred for 10min, and allowed to warm up to ambient temperature and stirred for 6hrs. Obtained mixture was quenched with cold saturated NH4CI (3x30ml_), organic bottom phase was separated and top aqueous layer was extracted with dichloromethane (2x30ml). Combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 4.34g of clear viscous oil. This crude was purified by chromatography on silica gel using dichloromethane/methanol as eluent with gradient from 0% to 15%methanol. Pure fractions were collected and concentrated under reduced pressure to give 2.63g (99% yield) of product as clear oil. 1HNMR (400MHz, CDCI3, δ): 7.81 and 7.69 (2m, 4H, phthalimido), 7.63 (s, 1 H, triazole), 7.1 1 and 6.87 (2d, 4H, tyrosine), 6.92 (d, 1 H, NH), 6.60 (s, 1 H, NH), 6.74(m, 1 H, NH), 5.15 (s, 2H, 0-CH2-triazole), 5.04 (broad s, 1 H, NH-BOC), 4.57 (q, 1 H, N-CH-CO), 4.47(t, 2H, CH2-triazole), 3.86 (t, 2H, CH2-N-phtalimido), 3.70 (t, 2H, CH2N), 3.68-3.42 (m, 60H, CH20, and CH2N), 2.98 (dddd, 2H, CH2- C6H4-0), 2.42 (t, 2H, CH2CO), 1 .41 (s, 9H, t-Bu).
  • 6
  • [ 854601-60-8 ]
  • 2,5,8,11,14,17,20,23,26,29,32-undecaoxa-35-azaoctatriacontan-38-oic acid [ No CAS ]
  • 7
  • [ 854601-60-8 ]
  • 2,5-dioxopyrrolidin-1-yl 35-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl)-2,5,8,11,14,17,20,23,26,29,32-undecaoxa-35-azaoctatriacontan-38-oate [ No CAS ]
  • 8
  • [ 854601-60-8 ]
  • [ 2495-35-4 ]
  • benzyl 2,5,8,11,14,17,20,23,26,29,32-undecaoxa-35-azaoctatriacontan-38-oate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; N,N-dimethyl-formamide; [0001208] To a mixture of 2,5,8,1 l,14,17,20,23,26,29,32-undecaoxatetratriacontan-34-amine (1 g) in N,N-dimethylformamide (4 mL) and water (3 mL) was added benzyl acrylate (0.377 g), dropwise. The reaction mixture was stirred overnight purified by reverse-phase HPLC on a Gilson system (CI 8 column), eluting with 20-70% acetonitrile in water containing 0.1% trifluoroacetic acid, to give the title compound. MS (ESI) m/e 678.4 (M+H)+.
In water; N,N-dimethyl-formamide; To a mixture of <strong>[854601-60-8]2,5,8,11,14,17,20,23,26,29,32-undecaoxatetratriacontan-34-amine</strong> (1 g) in N,N-dimethylformamide (4 mL) and water (3 mL) was added benzyl acrylate (0.377 g), dropwise. The reaction mixture was stirred overnight purified by reverse-phase HPLC on a Gilson system (C18 column), eluting with 20-70% acetonitrile in water containing 0.1% trifluoroacetic acid, to give the title compound. MS (ESI) m/e 678.4 (M+H)+.
In water; N,N-dimethyl-formamide; To a mixture of 2,5,S,II,I4,17,20,23,26,29,32-undecaoxatetratriacontan-34-amine (1 g) inN,N-dimethylformamide (4 mL) and water (3 mL) was added benzyl acrylate (0.377 g), dropwise.20 The reaction mixture was stirred overnight purified by reverse-phase HPLC on a Gilson system (CIS2530column), eluting with 20-70% acetonitrile in water containing O.I% trifluoroacetic acid, to give thetitle compound. MS (ESI) m/e 67S.4 (M+Ht
In water; N,N-dimethyl-formamide; To a mixture of <strong>[854601-60-8]2,5,8,11,14,17,20,23,26,29,32-undecaoxatetratriacontan-34-amine</strong> (1 g) in N,N-dimethylformamide (4 mL) and water (3 mL) was added benzyl acrylate (0.377 g), dropwise. The reaction mixture was stirred overnight purified by reverse-phase HPLC on a Gilson system (C18 column), eluting with 20-70% acetonitrile in water containing 0.1% trifluoroacetic acid, to give the title compound. MS (ESI) m/e 678.4 (M+H)+.

  • 9
  • [ 854601-60-8 ]
  • [ 2419-94-5 ]
  • C56H111N3O26 [ No CAS ]
YieldReaction ConditionsOperation in experiment
450 mg With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 4℃; for 29.75h;Inert atmosphere; Boc-L-Glu (134.9 mg) and BOP (724 mg) were dissolved in anhydrous DMF (4 mL) andwere stirred at 0 C under a nitrogen atmosphere. This solution was then added to a solutionof H2N-PEG(12u)-Me (685 mg) and NIVI1VI (179.8 1iL) in DMF (3 mL), which had previously been stirred for 75 mm. The combined solution was then stirred under nitrogen at 0 C for 4.5 h. Additional BOP (241 mg) and NIVI1VI (60 1iL) were added and the reaction mixture left for 24 h at 4 C. The volatiles were removed in vacuo and the resulting residue was purified by reverse phase C 18-column chromatography eluting with eluting with buffer A (v/v):water:5% acetonitrile:0.1% formic acid and buffer B (v/v): acetonitrile:0.1% formic acid (100:0 v/v to 65:3 5 v/v). The organic solvent was removed in vacuo and the aqueous solvent was removed by lyophilisation. The material was repurified by normal phase flash chromatography eluting with ethyl acetate:methanol (100:0 v/v to 0:100 v/v). The organic solvent was removed in vacuo and the aqueous solvent was removed by lyophilisation to givecompound 15 as a colourless oil (450 mg). m/z [M+H] (1331, 100%), [M+2H]2 (666,100%).
  • 10
  • [ 854601-60-8 ]
  • [ 180516-87-4 ]
  • 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5,8,11,14,17,20,23,26,29,32,35-undecaoxaazahexatriacontan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; 4-(4,4,5,5-Tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoic acid (100 mg) and2,5,8,1 l,14,17,20,23,26,29,32-undecaoxatetratriacontan-34-amine (229 mg) were dissolved in dichloromethane (2 mL). N1-((Ethylimino)methylene)-N3^V3-dimethylpropane-l,3-diaminehydrochloride (162 mg) and NN-dimethylpyridin-4-amine (73.9 mg) were added. The solution was mixed at room temperature overnight. The solution was concentrated under vacuum and purified by flash column chromatography using a gradient of 0-20% methanol in dichloromethane. The solvent was removed under vacuum to yield the title compound. 'H NMR (500 MHz, dimethylsulfoxide-cfe) δ ppm 8.56 (t, IH), 7.85 (d, 2H), 7.74 (d, 2H), 3.56-3.46 (m, 44H), 3.24 (s, 3H), 1.31 (s, 12H). MS (ESI) m/z 763.0 (M+NH4)+.
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