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[ CAS No. 89889-52-1 ] {[proInfo.proName]}

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Chemical Structure| 89889-52-1
Chemical Structure| 89889-52-1
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Quality Control of [ 89889-52-1 ]

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Product Details of [ 89889-52-1 ]

CAS No. :89889-52-1 MDL No. :MFCD00467154
Formula : C26H41N5O7S Boiling Point : -
Linear Structure Formula :- InChI Key :ATYCFNRXENKXSE-MHPIHPPYSA-N
M.W : 567.70 Pubchem ID :16219024
Synonyms :
Chemical Name :2,5-Dioxopyrrolidin-1-yl 6-(6-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)hexanamido)hexanoate

Safety of [ 89889-52-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 89889-52-1 ]

* 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 [ 89889-52-1 ]

[ 89889-52-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 29390-67-8 ]
  • [ 89889-52-1 ]
  • C58H96N4O37S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 40℃; for 24h; General procedure: Biotin tethering to cyclooligosaccharides starts from monotosylation on the primary hydroxylgroup, but the monotosylation method of both cyclooligosaccharides slightly differed from each other.For monotosylation of beta-CD, beta-CD (10.0 g, 8.8 mmol) was dissolved in water (250 mL) and heated to60 °C. After cooling to room temperature, 1-(p-toluenesulfonyl) imidazole (6 g, 27 mmol) was addedand mixed for 6 h. Sodium hydroxide (4.5 g, 112.5 mmol) solution in water (12.5 mL) was addeddropwise for 20 min. After filtration, the filtrate was quenched using ammonium chloride (12.05 g,225 mmol), and the resulting mixture was subjected to air flow for drying. The precipitated productwas washed with water and acetone. The yield of monotosylated beta-CD was 28percent. For monotosylatedCyS, CyS (1 g, 0.28 mmol) was dissolved in water (50 mL), and copper sulfate (1 g, 4 mmol) in water(100 mL), was added. NaOH (1 g, 25 mmol) solution in water (50 mL) was mixed and stirredfor 10 min. The suspension became dark blue, and p-toluenesulfonyl chloride (2.5 g, 13.2 mmol)dissolved in 0.1 mL of acetonitrile was added in a dropwise manner for 1 h. The suspension wasstirred at room temperature for 4 h then neutralized with ammonium chloride. After removing the precipitate, the filtrate was concentrated and desalted on a Bio-Gel P2 column. The sample wassubjected to semi-preparative HPLC (Agilent Technologies 1200 series, Santa Clara, CA, USA) on areverse-phase column (Eclipse XDB-C18, 9.4 x 250 mm, 5 mum) at room temperature. The yieldof monotosylated CyS was 25percent. Further azidation and amination were performed, as describedin our previous report [43,44]. The mono-6-amino-beta-CD or mono-6-amino-CyS were dissolved inDMF and reacted with biotinamidohexanoic acid N-hydroxysuccinimide ester for 24 h at 40 °C.After acetone precipitation, the samples were desalted and lyophilized. The overall synthetic yield fromoriginal cyclooligosaccharide to biotinylated one is about 8percent. The structures of the resulting biotinylcyclooligosaccharides were analyzed by NMR spectroscopy and MALDI-TOF mass spectrometry.
  • 2
  • [ 6066-82-6 ]
  • [ 72040-64-3 ]
  • [ 89889-52-1 ]
YieldReaction ConditionsOperation in experiment
71% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 48h; The commercial product 6-Biotinylamino-hexanoic acid (Biotin-Ahx-OH, 101 mg, 0.28 mmol) was dissolved in 4 ml of DMF (light suspension). N-hydroxy succinimide (NHS, 36 mg, 0.31 mmol) and N-(3-Dimethylaminopropyl)-N' ethyl-carbodiimide (EDC x HCI, 59 mg, 0.31 mmol.) were added to reaction mixture and stirred at room temperature for 2 days following disappearance of the acid on TLC analysis. Then, the organic solvent was evaporated under high vacuum and the obtained residue was dissolved in CH2CI2 (20 ml) and rapidly washed with 0.1 N HCI solution to remove excess reagents. The combined organic phase were washed with brine (20 ml), dried over anhydrous Na2S04, filtered and concentrated to give a white solid Biotin-OSu activated (91 mg, yield 71 percent), used immediately without further purification.
  • 3
  • [ 74124-79-1 ]
  • [ 72040-64-3 ]
  • [ 89889-52-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 2.25h; To a suspension of compound 9 (1 eq., 520 mg, 1.45 mmol) in DMF (25.5 mL) weresubsequently added N,N-disuccinimidyl carbonate (2.5 eq., 931 mg, 3.64 mmol) and TEA(2 eq., 294 mg, 0.404 mL, 2.91 mmol). After 15 minutes the precipitate solubilized, stirringcontinued for 2h at room temperature. lOx volume of Et20 was then added and theobtained precipitate was filtered to yield the crude product, which was recrystallized froma minimum amount of ACN to yield compound 10 as a white solid. The structure of 10 wasconfirmed by ESI-MS analysis (Method 1).ESI-MS m/z: 455.5 [M+H]
  • 4
  • [ 89889-52-1 ]
  • [ 60-32-2 ]
  • [ 89889-51-0 ]
YieldReaction ConditionsOperation in experiment
72.2% With triethylamine; In N,N-dimethyl-formamide; General procedure: A solution of Biotin (488 mg, 2.0 mmol, 1.0 equiv) in N, N-dimethylformamide(DMF, 20 ml) was added N-hydroxysuccinimide (NHS, 276 mg, 2.4 mmol, 1.2 equiv) and dicyclohexylcarbodiimide (DCC, 824 mg, 4.0 mmol, 2.0 equiv) and 4-dimethylaminopyridine(DMAP, 610 mg, 5.0 mmol, 2.5 equiv) at room temperature. The solution was stirred overnight, and then the solvent was removed under reduced pressure. The residue was dissolved in isopropanol (40 ml) with ultrasonic. The solution was cool to 4 C and stood for 1 h. The resulted mixture was filtered to afford intermediate a. Intermediate a (341 mg, 1.0 mmol, 1.0 equiv) and 6-aminocaproic acid(157 mg, 1.2 mmol, 1.2 equiv) were dissolved in 20 ml DMF. Triethylamine (0.3 ml,2.16 mmol, 2.16 equiv) was added. The solution was stirred overnight, and then the solvent was removed under reduced pressure. The residue was dissolved in water(25 ml) and formic acid (2 ml) with ultrasonic. The solution was cooled to 4 C. The resulted mixture was filtered to afford compound 1. Intermediate b was obtained according to the similar procedure of preparing intermediate a staring from 1. Compound 2 was obtained according to the similar procedure of preparing compound 1 staring from intermediate b. To a solution of biotin (400 mg, 2.0 mmol, 1.0equiv) and tributylamine (0.64 ml, 2.7 mmol, 1.3 equiv) in DMF (40 ml) was added isobutyl chloroformate (0.32 ml, 2.5 mmol, 1.2 equiv) at room temperature. The reaction mixture was stirred 10 min, and then 3-aminobenzoic acid (548 mg, 4.0 mmol,2.0 equiv) in 40 ml DMF was added slowly to the mixture at 0 C and left to stir for 2 h. The solvent was removed under reduced pressure. The residue was dissolved inwarm ethanol solution (50%, 36 ml). The pH of the mixture was adjusted to 2.0 by hydrochloric acid. The mixture was cooled to 0 C and stood for 12 h. The resulted mixture was filtered to give compound 3. Compounds 4a, 4 b and 4c were obtained according to the similar procedure of preparing 3 starting from 4-aminobenzoic acid, 4-amino-3-methylbenzoic acid and 4-amino-3-fluorobenzoic acid. The biotin derivatives were all white solids. Compound 1, 270 mg, yield 75.6%. Compound 2, 340 mg,yield 72.2%. Compound 3, 465 mg, yield 62.4%. Compound 4a, 483 mg, yield 64.9%. Compound 4b, 600 mg, yield 77.6%. Compound 4c, 465 mg, yield 62.4%.
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