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[ CAS No. 3326-34-9 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 3326-34-9
Chemical Structure| 3326-34-9
Structure of 3326-34-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3326-34-9 ]

CAS No. :3326-34-9 MDL No. :MFCD00005052
Formula : C20H13NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :GZAJOEGTZDUSKS-UHFFFAOYSA-N
M.W : 347.32 Pubchem ID :76845
Synonyms :
5-AF

Calculated chemistry of [ 3326-34-9 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.05
Num. rotatable bonds : 0
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 93.15
TPSA : 102.01 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : 2.74
Log Po/w (WLOGP) : 3.15
Log Po/w (MLOGP) : 1.94
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 2.46

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.23
Solubility : 0.0204 mg/ml ; 0.0000586 mol/l
Class : Moderately soluble
Log S (Ali) : -4.54
Solubility : 0.0101 mg/ml ; 0.0000291 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.79
Solubility : 0.000567 mg/ml ; 0.00000163 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.88

Safety of [ 3326-34-9 ]

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 [ 3326-34-9 ]

* 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 [ 3326-34-9 ]

[ 3326-34-9 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 108-24-7 ]
  • [ 3326-34-9 ]
  • [ 82779-14-4 ]
  • 2
  • [ 108-24-7 ]
  • [ 3326-34-9 ]
  • [ 82779-12-2 ]
  • 3
  • [ 77295-58-0 ]
  • [ 3326-34-9 ]
  • C28H27NO7 [ No CAS ]
  • 4
  • [ 3326-34-9 ]
  • [ 103483-32-5 ]
  • C32H39NO6Si [ No CAS ]
  • 5
  • [ 2307-00-8 ]
  • [ 108-46-3 ]
  • [ 3326-34-9 ]
  • [ 51649-83-3 ]
  • 8
  • [ 100-27-6 ]
  • [ 3326-34-9 ]
  • 5-Amino-2-{6-[2-(4-nitro-phenyl)-ethoxy]-3-oxo-9,9a-dihydro-3H-xanthen-9-yl}-benzoic acid 2-(4-nitro-phenyl)-ethyl ester [ No CAS ]
  • 9
  • [ 3326-34-9 ]
  • [ 153120-92-4 ]
  • 2',3',5'-tri-O-acetyl-N4-[(3',6'-dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-5-yl)amino]carbonyl}cytidine [ No CAS ]
  • 10
  • [ 3326-34-9 ]
  • 2'-deoxy-5'-O-[2-(4-nitrophenyl)ethoxy]carbonyl}-N6-(phenoxycarbonyl)adenylyl-{3'-{OP-[2-(4-nitrophenyl)ethyl]-5'}-2'-deoxy-N6,3'-O-bis[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine [ No CAS ]
  • [ 195875-00-4 ]
  • 11
  • [ 3326-34-9 ]
  • [ 195874-94-3 ]
  • 3',5'-di-O-acetyl-2'-deoxy-N2-[(3',6'-dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-5-yl)amino]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine [ No CAS ]
  • 12
  • [ 3326-34-9 ]
  • [ 153120-96-8 ]
  • [ 153120-98-0 ]
  • 13
  • [ 108-31-6 ]
  • [ 3326-34-9 ]
  • N-(5-fluoresceinyl)maleamic acid [ No CAS ]
  • 16
  • 3',6'-dihydroxy-5(?)-nitro-spiro<phthalan-1,9'-xanthen>-3-one [ No CAS ]
  • [ 3326-34-9 ]
  • 17
  • [ 3326-34-9 ]
  • [ 153120-99-1 ]
  • N6-{[3-carboxy-4-(6-hydroxy-3-oxo-3H-xanthen-9-yl)phenyl]amino}carbonyl}-2'-deoxy-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine [ No CAS ]
  • 18
  • [ 3326-34-9 ]
  • 2'-deoxy-5'-O-(dimethoxytrityl)-N6-(phenoxycarbonyl)adenylyl-{3'-{OP-[2-(4-nitrophenyl)ethyl]-5'}-2'-deoxy-N6,3'-O-bis[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine [ No CAS ]
  • 2'-deoxy-N6-[(3',6'-dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-5-yl)amino]carbonyl}-5'-O-(dimethoxytrityl)adenylyl-{3'-{OP-[2-(4-nitrophenyl)ethyl]-5'}-2'-deoxy-N6,3'-O-bis[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine [ No CAS ]
  • 19
  • [ 3326-34-9 ]
  • 2'-deoxy-N6,5'-O-bis[2-(4-nitrophenyl)ethoxy]carbonyl}adenylyl-{3'-{OP-[2-(4-nitrophenyl)ethyl]-5'}-2'-deoxy-N6-(phenoxycarbonyl)adenylyl-{3'-{OP-[2-(4-nitrophenyl)ethyl]-5'}-2'-deoxy-N6,3'-O-bis[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine [ No CAS ]
  • [ 153120-98-0 ]
  • 22
  • paclitaxel-10-deacetyl-10-carbonyl-N-methylimidazolinium iodide [ No CAS ]
  • [ 3326-34-9 ]
  • C78H90N2O19Si2 [ No CAS ]
  • 23
  • 2,5-bis-[4-(5-oxo-2-trifluoromethyl-4,5-dihydro-oxazol-4-yl)-phenoxymethyl]-benzoyl chloride [ No CAS ]
  • [ 3326-34-9 ]
  • C49H29F6N3O12 [ No CAS ]
  • 24
  • poly(methyl methacrylate-co-5-acryloylaminovaleric acid) [ No CAS ]
  • [ 3326-34-9 ]
  • polymer; monomer(s): methyl methacrylate; 5-acryloylaminovaleric acid; fluoresceinamine [ No CAS ]
  • 25
  • poly(methyl methacrylate-co-5-acryloylaminoheptanoic acid) [ No CAS ]
  • [ 3326-34-9 ]
  • polymer; monomer(s): methyl methacrylate; 5-acryloylaminoheptanoic acid; fluoresceinamine [ No CAS ]
  • 26
  • polymer; monomer(s): methyl methacrylate; 2-chloroethyl acrylate [ No CAS ]
  • [ 3326-34-9 ]
  • polymer; monomer(s): methyl methacrylate; 2-chloroethyl acrylate; fluoresceinamine [ No CAS ]
  • 27
  • poly[methyl methacrylate-co-(4-chlorobutyl acrylate)] [ No CAS ]
  • [ 3326-34-9 ]
  • polymer; monomer(s): methyl methacrylate; 4-chlorobutyl acrylate; fluoresceinamine [ No CAS ]
  • 28
  • [ 627-91-8 ]
  • [ 3326-34-9 ]
  • [ 227078-98-0 ]
  • 29
  • [ 3326-34-9 ]
  • [ 7693-46-1 ]
  • [ 882853-90-9 ]
YieldReaction ConditionsOperation in experiment
75 - 99% In acetone; Synthesis of a 1,3-cyclohexadione-fluorescein derivative. Condensation of commercial <strong>[3326-34-9]fluoresceinamine</strong> with p-nitrophenyl chloroformate gives a reactive carbamate that condenses with alcohol (3, Scheme 1) to produce a protected 1,3-cyclohexadione-fluorescein derivative (Scheme 5). Acidic deprotection of the enol ether group yields the desired probe in good yield (Scheme 5).
  • 30
  • [ 3326-34-9 ]
  • C67H70N8O17 [ No CAS ]
  • 38
  • [ 3326-34-9 ]
  • [ 227078-97-9 ]
  • 39
  • [ 3326-34-9 ]
  • Nα-[(5-fluoresceinyl)-5-carbamoylpentanoyl]-Nε-t-butyloxycarbonyllysine [ No CAS ]
  • 40
  • [ 3326-34-9 ]
  • C38H43N3O11 [ No CAS ]
  • 41
  • [ 3326-34-9 ]
  • C57H59N6O13P [ No CAS ]
  • 42
  • [ 3326-34-9 ]
  • C35H32N2O9 [ No CAS ]
  • 43
  • [ 3326-34-9 ]
  • C71H74N8O19 [ No CAS ]
  • 44
  • [ 3326-34-9 ]
  • N6-[(3',6'-dihidroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-5-yl)amino]carbonyl}adenosine [ No CAS ]
  • 45
  • [ 3326-34-9 ]
  • N6-{[4-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-3-(methoxycarbonyl)phenyl]amino}carbonyl}adenosine [ No CAS ]
  • 46
  • [ 3326-34-9 ]
  • 2',3',5'-tri-O-acetyl-N4-{[4-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-3-(methoxycarbonyl)phenyl]amino}carbonyl}cytidine [ No CAS ]
  • 48
  • [ 3326-34-9 ]
  • 2'-deoxy-N6-{[4-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-3-(methoxycarbonyl)phenyl]amino}carbonyl}-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine [ No CAS ]
  • 49
  • [ 3326-34-9 ]
  • 2',3',5'-tri-O-acetyl-N6-{{{4-{3-hydroxy-6-[(4-methoxyphenyl)carbonyl]oxy}-9H-xanthen-9-yl}-3-(methyoxycarbonyl)phenyl}amino}carbonyl}adenosine [ No CAS ]
  • 50
  • [ 3326-34-9 ]
  • 2',3',5'-tri-O-acetyl-N6-{{{4-{3-hydroxy-6-[2-(4-nitrophenyl)ethoxy]-9H-xanthen-9-yl}-3-(methoxycarbonyl)phenyl}amino}carbonyl}adenosine [ No CAS ]
  • 51
  • [ 3326-34-9 ]
  • 2',3',5'-tri-O-acetyl-N6-{{{4-{3-hydroxy-6-{[2-(4-nitrophenyl)ethoxy]carbonyl}oxy}-9H-xanthen-9-yl}-3-(methoxycarbonyl)phenyl}amino}carbonyl}adenosine [ No CAS ]
  • 52
  • [ 3326-34-9 ]
  • 2',3',5'-tri-O-acetyl-N6-{{{4-{3-hydroxy-6-[2-(4-nitrophenyl)ethoxy]-9H-xanthen-9-yl}-3-(methyoxycarbonyl)phenyl}amino}[2-(4-nitrophenyl)ethoxy]methylene}adenosine [ No CAS ]
  • 53
  • [ 3326-34-9 ]
  • 2',3',5'-tri-O-acetyl-N6-{{{4-{3-hydroxy-6-[2-(4-nitrophenyl)ethoxy]-9H-xanthen-9-yl}-3-[2-(4-nitrophenyl)ethoxy]carbonyl}phenyl}amino}carbonyl}adenosine [ No CAS ]
  • 54
  • [ 3326-34-9 ]
  • 2',3',5'-tri-O-acetyl-N6-{{{4-{3-hydroxy-6-[2-(4-nitrophenyl)ethoxy]-9H-xanthen-9-yl}-3-[2-(4-nitrophenyl)ethoxy]carbonyl}phenyl}amino}[2-(4-nitrophenyl)ethoxy]methylene}adenosine [ No CAS ]
  • 55
  • [ 3326-34-9 ]
  • [ 75350-46-8 ]
  • 56
  • [ 3326-34-9 ]
  • 2-{6-[2-(4-Nitro-phenyl)-ethoxy]-3-oxo-9,9a-dihydro-3H-xanthen-9-yl}-5-phenoxycarbonylamino-benzoic acid 2-(4-nitro-phenyl)-ethyl ester [ No CAS ]
  • 57
  • [ 3326-34-9 ]
  • 2-{6-[2-(4-Nitro-phenyl)-ethoxy]-3-oxo-9,9a-dihydro-3H-xanthen-9-yl}-5-{3-[9-((2R,3aS,9aR)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-9H-purin-6-yl]-ureido}-benzoic acid 2-(4-nitro-phenyl)-ethyl ester [ No CAS ]
  • 58
  • [ 3326-34-9 ]
  • C30H28ClNO8 [ No CAS ]
  • 59
  • [ 3326-34-9 ]
  • [ 111742-70-2 ]
  • 60
  • [ 3326-34-9 ]
  • C32H29Cl2NO9 [ No CAS ]
  • 61
  • [ 3326-34-9 ]
  • C36H41Cl2NO8Si [ No CAS ]
  • 62
  • [ 3326-34-9 ]
  • [ 111742-74-6 ]
  • 63
  • [ 3326-34-9 ]
  • C35H29IN2O10 [ No CAS ]
  • 64
  • [ 3326-34-9 ]
  • [ 111742-71-3 ]
  • 65
  • [ 3326-34-9 ]
  • [ 111742-76-8 ]
  • 66
  • [ 3326-34-9 ]
  • C37H33IN2O12 [ No CAS ]
  • 67
  • [ 3326-34-9 ]
  • [ 111742-73-5 ]
  • 68
  • [ 3326-34-9 ]
  • [ 111742-75-7 ]
  • 69
  • [ 3326-34-9 ]
  • C41H43IN2O11Si [ No CAS ]
  • 70
  • [ 3326-34-9 ]
  • [ 111742-72-4 ]
  • 71
  • [ 3326-34-9 ]
  • [ 82779-14-4 ]
  • 72
  • [ 652-12-0 ]
  • [ 3326-34-9 ]
  • [ 209540-90-9 ]
YieldReaction ConditionsOperation in experiment
With pyridine; hydrogenchloride; In sodium hydrogencarbonate; N,N-dimethyl-formamide; Example 27 Preparation of 5-(2'-carboxy-3',4',5',6'-tetrafluorobenzoylamino)fluorescein (27): 5-Aminofluorescein (1 g, 2.9 mmol) is dissolved in 10 mL of anhydrous N,N-dimethylformamide (DMF) that contains anhydrous pyridine (0.47 mL, 5.8 mmol). To the solution is added tetrafluorophthalic anhydride (660 mg, 3.0 mmol) in 5 portions over 5 h. The resulting mixture is stirred overnight. This reaction mixture is concentrated in vacuo, and the residue is poured into water (200 mL). The precipitate thus formed is collected by filtration and washed by water. The crude solid is taken up in 1M aqueous NaHCO3 solution (100 mL), and the resulting mixture is filtered. The filtrate is washed with ether (3*100 mL). The aqueous layer is carefully neutralized to pH 7.5 with 10% HCl and the resulting precipitate is collected by filtration and air-dried to give Compound 27 (939 mg, yield: 59%).
  • 73
  • [ 832-53-1 ]
  • [ 3326-34-9 ]
  • [ 209540-57-8 ]
YieldReaction ConditionsOperation in experiment
With pyridine; sodium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; Example 2 Preparation of 5-(pentafluorobenzenesulfonylamino)fluorescein (3): 5-Aminofluorescein (1 g, 2.9 mmol) is dissolved in 10 mL of anhydrous DMF containing anhydrous pyridine (0.57 mL, 5.8 mmol). To the solution is added dropwise 10 mL of an anhydrous dichloromethane solution of pentafluorobenzenesulfonyl chloride (0.64 mL, 4.4 mmol) at 0 C. under dry nitrogen protection. The resulting mixture is gradually warmed up to room temperature and stirred overnight. This reaction mixture is concentrated in vacuo, and the residue is poured into water (100 mL). The precipitate that is formed is collected and washed with water. The crude solid is redissolved in methanol (10 mL). To the solution is added dropwise 1M aqueous NaOH solution (3 mL, 3 mmol), and the resulting mixture is stirred at room temperature for 2 h. This reaction solution is neutralized with 10% HCl and concentrated in vacuo. The resulting suspension is diluted with water and filtered to collect the solid, which is then washed by water and air-dried. This treatment converts the diacylated and triacylated aminofluoresceins into the desired N-monoacylated product. The crude solid is chromatographed on a silica gel column using a gradient elution of chloroform/methanol to afford Compound 3 as a brown solid (652 mg, yield: 39%).
  • 74
  • [ 98-88-4 ]
  • [ 3326-34-9 ]
  • [ 126219-08-7 ]
YieldReaction ConditionsOperation in experiment
5-(Benzoylamino)fluorescein (Compound 2) is prepared similarly from 5-aminofluorescein and benzoyl chloride.
  • 75
  • [ 3326-34-9 ]
  • [ 177787-26-7 ]
  • [ 209540-87-4 ]
YieldReaction ConditionsOperation in experiment
Example 26 Preparation of 5-(3',4',5'-trifluorobenzoylamino)fluorescein (26): 5-Aminofluorescein (100 mg, 0.29 mmol) is reacted with 3,4,5-trifluorobenzoyl chloride (87 mg, 0.45 mmol) at 0 C. under dry nitrogen protection, and worked up according to the procedure of Example 1. Compound 26 is obtained as a brown solid (105 mg, yield: 72%).
  • 76
  • [ 2251-50-5 ]
  • [ 3326-34-9 ]
  • [ 209540-56-7 ]
YieldReaction ConditionsOperation in experiment
With pyridine; sodium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; Example 1 Preparation of 5-(pentafluorobenzoylamino)fluorescein (1) and 5-(benzoylamino)fluorescein (2): 5-Aminofluorescein (2 g, 5.8 mmol) is dissolved in 20 mL of anhydrous N,N-dimethylformamide (DMF) that contains anhydrous pyridine (0.94 mL, 11.6 mmol). To the solution is dropwise added 20 mL of an anhydrous dichloromethane solution of pentafluorobenzoyl chloride (1.3 mL, 8.7 mmol) at 0 C. under dry nitrogen protection. The resulting mixture is gradually warmed to room temperature and stirred overnight. This reaction mixture is concentrated in vacuo, and the residue is poured into water (200 mL). The precipitate thus formed is collected by filtration and washed with water. The crude solid is redissolved in methanol (20 mL). To the solution is dropwise added 1M aqueous NaOH solution (6 mL, 6 mmol), and the resulting mixture is stirred at room temperature for 2 h. This reaction solution is neutralized with 10% HCl and concentrated in vacuo. The resulting suspension is diluted with water and filtered to collect the solid, which is then washed with water and air-dried. This treatment converts the diacylated and triacylated aminofluoresceins into the desired N-monoacylated product. The crude solid is recrystallized from ethyl acetate to afford Compound 1 as brown crystals (2.1 g, yield: 67%).
  • 77
  • (1 phenylcyclohexyl))piperidinyl chloroformate [ No CAS ]
  • [ 3326-34-9 ]
  • [ 143328-89-6 ]
YieldReaction ConditionsOperation in experiment
In pyridine; EXAMPLE X 4-(5 fluoresceinylcarbamoyl)-1-(phenylcyclohexyl) piperidine 4 (1 (1 phenylcyclohexyl))piperidinyl chloroformate (10 mg) and 5-aminofluorescein (10 mg) were dissolved in 2 mL dry pyridine and stirred at room temperature for about 18 hours. The reaction was chromatographed on silica gel preparative plates eluted with the appropriate ratio of methanol, chloroform and acetic acid to yield the desired tracer.
  • 78
  • [ 72076-50-7 ]
  • [ 3326-34-9 ]
  • [ 1451092-40-2 ]
YieldReaction ConditionsOperation in experiment
Alkaline conditions; Commercially available aminoisophthalate dimethyl ether 53 is converted to the isothiocyanate 54 and that compound is reacted under basic conditions with aminofluorescein (isomer I) 55 to give the adduct 56. Following this reaction, the methyl esters are removed and TFP esters are formed to make the desired fluorescein containing homobifunctional linking reagent 58. Other bifunctional cross-linking reagents containing alternate chromophores can be prepared in a similar manner.
  • 79
  • [ 108-31-6 ]
  • [ 3326-34-9 ]
  • fluorescein-maleamic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetic acid; EXAMPLE VII Preparation of Fluorescein-5-maleamic acid A mixture of 350 milligrams (0.001 mols) of 5-aminofluorescein and 300 milligrams (excess) of maleic anhydride were mixed in 5.0 milliliters of glacial acetic acid and the mixture was stirred at ambient temperature for 24 hours. The yellow product formed was filtered off and washed three times with diethyl ether. 420 Milligrams of fluorescein-maleamic acid was obtained. 1. R (KBR) showed bands at 2.55; 3.28; 3.38; 4.05; 5.85; 6.30; 6.52; 6.88; 6.90; 7.70; 8.34; 8.52; and 8.30mu.
In acetic acid; EXAMPLE VII Preparation of Fluorescein-5-maleamic acid A mixture of 350 milligrams (0.001 mols) of 5-aminofluorescein and 300 milligrams (excess) of maleic anhydride were mixed in 5.0 milliliters of glacial acetic acid and the mixture was stirred at ambient temperature for 24 hours. The yellow product formed was filtered off and washed three times with diethyl ether. 420 Milligrams of fluorescein-maleamic acid was obtained. l. R (KBR) showed bands at 2.55; 3.28; 3.38; 4.05; 5.85; 6.30; 6.52; 6.88; 6.90; 7.70; 8.34; 8.52; and 8.30mu.
  • 80
  • 4-(1-(1-Phenylcyclohexyl)) piperidinyl Chloroformate [ No CAS ]
  • [ 3326-34-9 ]
  • [ 143328-89-6 ]
YieldReaction ConditionsOperation in experiment
In pyridine; EXAMPLE X 4-(5-Fluoresceinylcarbamoyl)-1-(phenylcyclohexyl) piperidine 4-(1-(1-Phenylcyclohexyl))piperidinyl chloroformate (10 mg) and 5-aminofluorescein (10 mg) were dissolved in 2 ml dry pyridine and stirred at room temperature for about 18 hours. The reaction was chromatographed on silica gel preparative plates eluted with the appropriate ratio of methanol, chloroform and acetic acid to yield the desired tracer.
  • 81
  • [ 107142-84-7 ]
  • [ 7285-11-2 ]
  • [ 3326-34-9 ]
  • [ 107142-68-7 ]
YieldReaction ConditionsOperation in experiment
In pyridine; 5-[4-{3-Methyl-3-ethyl-1-succinimidylmethyl} benzenesulfonamido] fluorescein 4-(3-Methyl-3-ethyl-1-succinimidylmethyl)benzene sulfonyl chloride (26 mg.) and 5-aminofluorescein (27.4 mg.) were dissolved in 250 ml. of pyridine and stirred for 45 minutes at room temperature. The product was purified by thin layer chromatography, developing with 4:1 chloroform-methanol and taking the band which migrated just above unreacted aminofluorescein.
  • 82
  • [ 3326-34-9 ]
  • [ 2321-07-5 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; In chloroform; acetic anhydride; acetic acid; 5-maleinimido Fluorescein 5-Aminofluorescein (500 mg, 1.44 mmol) is dissolved in 50 ml acetic acid/chloroform (1:1) (possibly suspension). Maleic acid anhydride (141 mg, 1.43 mmol) is added at room temperature and the mixture is stirred overnight. Thereafter, the solvent is removed in vacuo and the residue is taken up in acetic acid anhydride (30 ml). Sodium acetate (200 mg) is added and heated to 100 C. for 4 h. The reaction mixture is poured onto 100 ml ice water and extracted with acetic acid ethyl ester (3*100 ml). The organic phase is washed once with saturated NaCl solution and dried with magnesium sulfate. The solvent is removed in vacuo and the residue is chromatographed on silica gel (EtOAc/hexane 3:1). Yield: 590 mg ESI-MS: [M+H+] 512.0
  • 83
  • [ 2777-65-3 ]
  • [ 3326-34-9 ]
  • C31H31NO6 [ No CAS ]
  • 85
  • [ 1207997-54-3 ]
  • [ 3326-34-9 ]
  • [ 1207997-64-5 ]
  • 86
  • [ 1207997-55-4 ]
  • [ 3326-34-9 ]
  • [ 1207997-65-6 ]
  • 87
  • [ 3326-34-9 ]
  • [ 79-04-9 ]
  • [ 949535-56-2 ]
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