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Chemical Structure| 59253-71-3 Chemical Structure| 59253-71-3

Structure of 59253-71-3

Chemical Structure| 59253-71-3

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Product Details of [ 59253-71-3 ]

CAS No. :59253-71-3
Formula : C6H5N3O2
M.W : 151.12
SMILES Code : O=C(C1=C(C#N)N=CN1)OC

Safety of [ 59253-71-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 59253-71-3 ]

* 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 [ 59253-71-3 ]

[ 59253-71-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 59253-71-3 ]
  • [ 163226-45-7 ]
  • (1'S,2'R,3'R)-5-(cyanomethyl)-3-[2',3'-(isopropylidenedioxy)-4'-(trityloxymethyl)-4'-cyclopenten-1'-yl]-3H-imidazole-4-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -78 - 20℃; On the basis of the Mitsunobu reaction of 5 with 7 or 15a-b, the condensation reaction of 5 with imidazol derivative (19) or a protected 3-deazaguanine (23) was initially investigated with the Mitsunobu reaction in order to synthesize carbocyclic 3-deazaguanosine (4). The coupling reaction of 5 with 19, which was prepared from 18 by following the previously reported method,16 provided N7-isomer (20) in 91% yield using the condition OfPh3P and DIAD in THF. The precursor 20 was subsequently converted to carbocyclic N7-3- deazaguanosine (21) in 56% yield (2 steps) by using methamolic ammonia and hydrogen chloride. The structure of 21 was determined by H- and C-NMR, as well as UV data (lambdamax 261 and 317 nm, pH 7.0), which was compared with previously reported data for N7-3- deazaguanosine (3).16b Furthermore, the Mitsunobu reaction of 5 with a protected 3- deazaguanine (23), which was synthesized from 19 by using cyclization with ammonia in a steel bomb and protection with isobutanoic anhydride, afforded a mixture of N9/N7-isomer (ratio 1 : 1) in 20% yield along with several by-products. Therefore, we investigated a more efficient condensation reaction in order to enhance the amount of Ncrisomer and reaction yield. The hydroxy group of 5 was transformed to a methansufonyl (Ms) group with MsCl in 92% yield.10 The substitution reaction of 22 with 23 in the presence of NaH and DMF solution gave Ncrisomer (24) in 40% yield along with 5% of N7-isomer (25), which could easily be removed from 24 by using silica gel column chromatography. The structure of 24 was determined with 1-D NOE and 1H- and 13C-NMR, as well as UV data ((lambdamax 271 and 300 nm, pH 7.0). AU data was consistent with 3-deazaguanosin (3) from previously reported literatures.1613 The significant interaction between the C1 '-H and aromatic C3-H of 24 was observed in NOE experiment as shown in figure 2. Subsequently, the compound 24 was treated with methalolic ammonia, followed by aqueous 0.1 M HCl solution to afford carbocyclic 3-deazaguanosine (C-3-DG, 4) in an 11% yield from imidazole derivative (19). In the case of the synthesis of C-3-DG (4), this simple substitution reaction was a more convenient strategy than the Mitsunobu reaction both by regioselectivity (Ng) and overall yield. ; To a solution of 5 (0.5 g, 1.16 mmol) in anhydrous THF (25 niL), PPh3 (0.61 g, 2.33 tnmol) and 19 (0.29 g, 1.75 mmol) was added under N2 atmosphere at room temperature. The mixture was cooled to -78 0C. DIAD (0.46 mL, 2.33 mmol) was slowly added to this mixture and stirred for over night at rt. The mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexane:EtOAc = 4:1) to give compound 20 (0.61 g, 91%) as a white solid, mp 52C; [alpha]25D 31.02 (c 1.1, CHCl3); UV (MeOH) lambdamax 207, 232; 1H-NMR (CDCl3, 500 MHz) delta 7.47-7.44 (m, 7H), 7.33-7.25 (m, 9H), 6.03 (s, IH), 5.98 (s, IH), 5.09 (d, J = 5.5 Hz, IH), 4.50 (d, J= 5.5 Hz, IH), 4.03 (dd, J = 2.5, 15.5 Hz, IH), 4.01 (d, J= 2.5 Hz, 2H), 3.98 (s, 3H), 3.83 (d, J= 15.5 Hz, IH), 1.40 (s, 3H), 1.31 (s, 3H); 13C-NMR (CDCl3, 125 MHz) delta 160.1, 151.1, 143.6, 140.7, 138.5, 128.5, 128.0, 127.3, 121.4, 119.6, 116.7, 112.5, 87.3, 85.2, 83.5, 67.1, 61.2, 52.2, 27.5, 26.2, 19.3; HRMS (ES) calcd for C35H33N3O5 (M+H*) 576.2499, found 576.2403.
 

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