Home Cart 0 Sign in  

[ CAS No. 4105-39-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 4105-39-9
Chemical Structure| 4105-39-9
Structure of 4105-39-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 4105-39-9 ]

Related Doc. of [ 4105-39-9 ]

Alternatived Products of [ 4105-39-9 ]

Product Details of [ 4105-39-9 ]

CAS No. :4105-39-9 MDL No. :
Formula : C11H15N5O4S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 313.33 Pubchem ID :-
Synonyms :

Safety of [ 4105-39-9 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 4105-39-9 ]

* 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 [ 4105-39-9 ]

[ 4105-39-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 43157-50-2 ]
  • [ 74-88-4 ]
  • [ 4105-39-9 ]
YieldReaction ConditionsOperation in experiment
89% General procedure: 2-Thioadenosine (300 mg, 1 mmol) was dissolved with stirring in 7.5 ml DMF. Sodium dithionite (750 mg) was added and the mixture was stirred for 30 min under Ar. The reaction mixture was cooled in ice, aqueous sodium hydroxide (50% (w/w) solution (240 mg, 3 mmol) was added, and after 10 min stirring the alkyl iodide (1.1 mmol) was added dropwise over 10 min. The cooling was removed, and after 1 h stirring at rt the reaction mixture was analyzed by LCMS. If unreacted starting material was present an additional amount of alkyl iodide (0.134 mmol, 0.2 eqv.) was added with ice cooling, and after 1 h stirring at room temperature the analysis was repeated. When no starting material was present the reaction mixture was diluted with 75 ml of water and after ca. 2 h stirring the crude product was collected by filtration and washed with water. This material was purifiedby column chromatography on silica gel using chloroform/methanol as eluent. 2-Methylthioadenosine Prepared by the above general procedure from methyl iodide. Yield, 89%; 1H NMR (DMSO-d6) delta: 8.22 (s, 1H),7.35 (bs, 2H), 5.83 (d, J = 5.9 Hz, 1H), 5.21 (bs, 3H, OH), 4.62 (dd, J = 5.8, 4.9 Hz, 1H), 4.15 (dd, J = 3.5, 4.8Hz, 1H), 3.91 (m, 1H), 3.64 (dd, J = 4.3, 11.8 Hz, 1H), 3.53 (dd, J = 4.3, 11.8 Hz, 1H), 2.47 (s, 3H). MS (ESI+):314.1 [M+H]+; MS (ESI-): m/z 312.1 [M-H]-, 358.1 [M+formate]-; purity, 97.2%, RT 4.36 min (gradient from0.1 to 100% MeCN in 0.1% aqueous formic acid for 14 min).
With sodium hydride; In N,N-dimethyl-formamide; at 20℃; Example 1: Synthesis of compound 2, tetrasodium P1 ,P4-bis-(2-methylthio-5'- adenosine)tetraphosphate. Compound 2 was synthesized according to the following reaction scheme:ZnCI2, DMF, rt NaCIO4/acetone 2-Thioadenosine (prepared as disclosed in US patent 3,989,683) was S- methylated with 1.1 equivalents of methyl iodide in the presence of 1.2 equivalents of sodium hydride in anhydrous in N,7V-dimethylformamide at room temperature (step a). 2-Methylthioadenosine was converted to 2-methylthioadenosine-5'- monophosphate (step b) by the method of Yoshikawa et al. (Tetrahedr. Lett. 1967, 6065-5068). The disodium salt of di-(l-imidazolyl)diphosphonic acid was prepared as disclosed in WO 2008/024169 from pyrophosphate and carbonyldiimidazole (steps c, and d).2?/s-triethylammonium salt of 2-methylthioadenosine-5'-monophosphate (179 mg, 0.30 mmol) was dissolved in anhydrous DMF (5 ml), and the solvent was evaporated under high vacuum (0.2 mm Hg) at 35 C to produce a foam. The residue was dissolved in anhydrous DMF (5 ml) under nitrogen. Disodium salt of di-(l- imidazolyl)diphosphonic acid (32.2 mg, 0.1 mmol) was added to this solution, followed by anhydrous zinc chloride (408.9 mg, 3.0 mmol). The mixture was protected from moisture, stirred for 30 minutes, and then added to a stirred mixture of Chelex 100 resin in the sodium form (10 ml, Sigma-Aldrich Corp. St. Louis, MO) and 0.1 M triethylammonium acetate buffer (20 ml, pH 8). After stirring for 15 minutes the mixture was filtered, and the resin was washed two times with water (10 ml each). The combined filtrate and washings were loaded on a column of QEA- Sephadex (2.5 x 30 cm, Sigma-Aldrich Corp. St. Louis, MO) in the triethylammonium form, which was pre-equilibrated with 2 column volumes of 0.1 M triethylammonium bicarbonate buffer containing 10% (v/v) acetonitrile. A linear gradient of triethylammonium bicarbonate containing 10% (v/v) acetonitrile, from 0.1 to 1.5 M for 800 min, was passed through the column at a rate of 3 ml/min. The fractions containing the product were combined and evaporated under vacuum. The residue was re-evaporated three times from methanol (50 ml each), dissolved in methanol (0.5 ml) and mixed with a 2.0 M solution of sodium perchlorate in acetone (5 ml). The mixture was diluted with acetone (15 ml) and stirred for 2 hours. The white solid was collected by centrifugation, and washed by suspending in acetone (20 ml), centrifugation, and decanting. This acetone washing was repeated two more times, to give, after drying for 6 hours at high vacuum, 68.1 mg (67%) of compound 2. 1H NMR (300 MHz, D2O) delta 8.15 (2H, s, H-8), 5.94 (2H, d, J= 5.79 Hz, H-I '), 4.75 - 4.68 (2H, m, H-2'), 4.49 (2H, dd, J, = 3.9 Hz, J2 = 4.8 Hz, H-3'), 4.32 - 4.26 (2H, m, H-4'), 4.23 - 4.17 (4H, m, H-5'), 2.46 (6H, s, SCH3). 31P NMR (1H dec, 121 MHz, D2O), ppm: -l 1.01 - -1 1.36 (m, P'+P4), -22.45 - -22.81 (m, P2+P3).Electrospray MS in the negative ionization mode: Observed, 927.2 (100.0%), 928.1 (26.3%), 929.1 (15.9%), 930.1 (3.9%), 931.1 (0.9%); Calculated for [M-H]", C22H31N10O19P4S2-, m/e: 927.0 (100.0%), 928.0 (30.2%), 929.0 (17.4%), 930.0 (4.2%), 931.0 (1.2%).
  • 4
  • [ 15465-92-6 ]
  • [ 4105-39-9 ]
  • 5
  • [ 146-77-0 ]
  • [ 616-38-6 ]
  • [ 4105-39-9 ]
YieldReaction ConditionsOperation in experiment
77% With potassium <i>tert</i>-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Inert atmosphere; 36 Example 36 Under a nitrogen atmosphere,The substrate 2-chloroadenosine 1aa (0.1 mmol, 30.0 mg) was added to a 25 mL test tube reactor, KSAc(0.3mmol,34.2mg),DMC(0.5mmol,45mg),Pd(OAc)2(0.01mmol,2.3mg),PPh3 (0.02mmol,5.9mg),tBuOK(0.3mmol,34.6mg),and DMSO(1.5mL). The reaction was heated to 120 ° C to carry out the reaction.After the TLC detection reaction was completed,The system was cooled to room temperature.The reaction was quenched with saturated aqueous ammonium chloride,And extracted with ethyl acetate (3 * 10 mL)The column chromatography gave the product 3a 24.1 mg (77%).
Same Skeleton Products
Historical Records