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Synlett

Volumn , Issue 20, 2006, Pages 3474-3478

Pyridine-free and solvent-free acetylation of nucleosides promoted by molecular sieves

(2) Sá, Marcus Mandolesi a Meier, Lidiane a

a FEDERAL UNIVERSITY OF SANTA CATARINA (Brazil)

Author keywords

Acylation; Green chemistry; Heterogeneous catalysis; Molecular sieves; Nucleosides

Indexed keywords

ACETIC ANHYDRIDE; NUCLEOSIDE DERIVATIVE; POTASSIUM; PURINE; PYRIDINE; PYRIMIDINE; SOLVENT;

ACETYLATION; ACYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; ENVIRONMENT; SYNTHESIS;

EID: 33846509839 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2006-958430 Document Type: Article

Times cited : (18)

References (43)

1
- 0036558477
- (a) Pathak, T. Chem. Rev. 2002, 102, 1623.
- (2002) Chem. Rev , vol.102 , pp. 1623
- Pathak, T.¹

2
- 1842790913
- (b) Gupte, A.; Buolamwini, J. K. Bioorg. Med. Chem. Lett. 2004, 14, 2257.
- (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 2257
- Gupte, A.¹ Buolamwini, J.K.²

3
- 15444379778
- (c) Santaniello, E.; Ciuffreda, P.; Alessandrini, L. Synthesis 2005, 509.
- (2005) Synthesis , pp. 509
- Santaniello, E.¹ Ciuffreda, P.² Alessandrini, L.³

4
- 30344486584
- (d) De Clercq, E.; Field, H. J. Brit. J. Pharmacol. 2006, 147, 1.
- (2006) Brit. J. Pharmacol , vol.147 , pp. 1
- De Clercq, E.¹ Field, H.J.²

5
- 0034069172
- (a) Hocek, M.; Hol, A.; Votruba, I.; Dvoráková, H. J. Med. Chem. 2000, 43, 1817.
- (2000) J. Med. Chem , vol.43 , pp. 1817
- Hocek, M.¹ Hol, A.² Votruba, I.³ Dvoráková, H.⁴

6
- 0035861620
- (b) Véliz, E. A.; Beal, P. A. J. Org. Chem. 2001, 66, 8592.
- (2001) J. Org. Chem , vol.66 , pp. 8592
- Véliz, E.A.¹ Beal, P.A.²

7
- 0034597503
- (c) Lin, X.; Robins, M. J. Org. Lett. 2000, 2, 3497.
- (2000) Org. Lett , vol.2 , pp. 3497
- Lin, X.¹ Robins, M.J.²

8
- 0030961821
- (d) Prasad, A. S. B.; Stevenson, T. M.; Citineni, J. R.; Nyzam, V.; Knochel, P. Tetrahedron 1997, 53, 7237.
- (1997) Tetrahedron , vol.53 , pp. 7237
- Prasad, A.S.B.¹ Stevenson, T.M.² Citineni, J.R.³ Nyzam, V.⁴ Knochel, P.⁵

9
- 0024315358
- (e) Danishefsky, S. J.; DeNinno, S. L.; Chen, S.-H.; Boisvert, L.; Barbachyn, M. J. Am. Chem. Soc. 1989, 111, 5810.
- (1989) J. Am. Chem. Soc , vol.111 , pp. 5810
- Danishefsky, S.J.¹ DeNinno, S.L.² Chen, S.-H.³ Boisvert, L.⁴ Barbachyn, M.⁵

10
- 84982068675
- (f) Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.
- (1981) Chem. Ber , vol.114 , pp. 1234
- Vorbrüggen, H.¹ Krolikiewicz, K.² Bennua, B.³

11
- 0003463148
- 2nd ed, John Wiley and Sons: New York
- Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley and Sons: New York, 1991.
- (1991) Protective Groups in Organic Synthesis
- Greene, T.W.¹ Wuts, P.G.M.²

12
- 84943870548
- (a) Bredereck, H.; Martini, A. Chem. Ber. 1947, 80, 401.
- (1947) Chem. Ber , vol.80 , pp. 401
- Bredereck, H.¹ Martini, A.²

13
- 27144449937
- (b) Ren, B.; Cai, L.; Zhang, L.-R.; Yang, Z.-J.; Zhang, L.-H. Tetrahedron Lett. 2005, 46, 8083.
- (2005) Tetrahedron Lett , vol.46 , pp. 8083
- Ren, B.¹ Cai, L.² Zhang, L.-R.³ Yang, Z.-J.⁴ Zhang, L.-H.⁵

14
- 0141632675
- (c) Nowak, I.; Robins, M. J. Org. Lett. 2003, 5, 3345.
- (2003) Org. Lett , vol.5 , pp. 3345
- Nowak, I.¹ Robins, M.J.²

15
- 84989148287
- (a) Matsuda, A. Synthesis 1986, 385.
- (1986) Synthesis , pp. 385
- Matsuda, A.¹

16
- 12344269069
- (b) Gupta, M.; Nair, V. Tetrahedron Lett. 2005, 46, 1165.
- (2005) Tetrahedron Lett , vol.46 , pp. 1165
- Gupta, M.¹ Nair, V.²

17
- 1542345048
- (c) Jagtap, P. G.; Chen, Z.; Szabo, C.; Klotz, K.-N. Bioorg. Med. Chem. Lett. 2004, 14, 1495.
- (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 1495
- Jagtap, P.G.¹ Chen, Z.² Szabo, C.³ Klotz, K.-N.⁴

18
- 33645399030
- (a) Clark, J. H. Green Chem. 2006, 8, 17.
- (2006) Green Chem , vol.8 , pp. 17
- Clark, J.H.¹

19
- 27744506849
- (b) da Silva, F. M.; de Lacerda, P. S. B.; Jones, J. Quim. Nova 2005, 28, 103.
- (2005) Quim. Nova , vol.28 , pp. 103
- da Silva, F.M.¹ de Lacerda, P.S.B.² Jones, J.³

20
- 0036736355
- (c) Anastas, P. T.; Kirchhoff, M. M. Acc. Chem. Res. 2002, 35, 686.
- (2002) Acc. Chem. Res , vol.35 , pp. 686
- Anastas, P.T.¹ Kirchhoff, M.M.²

21
- 0742269497
- (a) Sartori, G.; Ballini, R.; Bigi, F.; Bosica, G.; Maggi, R.; Righi, P. Chem. Rev. 2004, 104, 199.
- (2004) Chem. Rev , vol.104 , pp. 199
- Sartori, G.¹ Ballini, R.² Bigi, F.³ Bosica, G.⁴ Maggi, R.⁵ Righi, P.⁶

22
- 0344255816
- (b) Corma, A.; Garcia, H. Chem. Rev. 2003, 103, 4307.
- (2003) Chem. Rev , vol.103 , pp. 4307
- Corma, A.¹ Garcia, H.²

23
- 0031486230
- (c) Clark, J. H.; Macquarrie, D. J. Org. Process Res. Dev. 1997, 1, 149.
- (1997) Org. Process Res. Dev , vol.1 , pp. 149
- Clark, J.H.¹ Macquarrie, D.J.²

24
- 0032934388
- (a) Bhaskar, P. M.; Loganathan, D. Synlett 1999, 129.
- (1999) Synlett , pp. 129
- Bhaskar, P.M.¹ Loganathan, D.²

25
- 0037764004
- (b) Adinolfi, M.; Barone, G.; Iadonisi, A.; Schiattarella, M. Tetrahedron Lett. 2003, 44, 4661.
- (2003) Tetrahedron Lett , vol.44 , pp. 4661
- Adinolfi, M.¹ Barone, G.² Iadonisi, A.³ Schiattarella, M.⁴

26
- 0035817170
- (c) Yadav, V. K.; Babu, K. G.; Mittal, M. Tetrahedron 2001, 57, 7047.
- (2001) Tetrahedron , vol.57 , pp. 7047
- Yadav, V.K.¹ Babu, K.G.² Mittal, M.³

27
- 0346502271
- (d) Yadav, V. K.; Babu, K. G. J. Org. Chem. 2004, 69, 577.
- (2004) J. Org. Chem , vol.69 , pp. 577
- Yadav, V.K.¹ Babu, K.G.²

28
- 0001516761
- (e) Breton, G. W. J. Org. Chem. 1997, 62, 8952.
- (1997) J. Org. Chem , vol.62 , pp. 8952
- Breton, G.W.¹

29
- 33744477112
- (f) Heravi, M. M.; Behbahani, F. K.; Bamoharram, F. F. J. Mol. Catal. A: Chem. 2006, 253, 16.
- (2006) J. Mol. Catal. A: Chem , vol.253 , pp. 16
- Heravi, M.M.¹ Behbahani, F.K.² Bamoharram, F.F.³

30
- 0033693463
- (g) Kumareswaran, R.; Pachamuthu, K.; Vankar, Y. D. Synlett 2000, 1652.
- (2000) Synlett , pp. 1652
- Kumareswaran, R.¹ Pachamuthu, K.² Vankar, Y.D.³

31
- 3242786314
- (a) Sá, M. M.; Silveira, G. P.; Castilho, M. S.; Pavão, F.; Oliva, G. ARKIVOC 2002, (viii), 112.
- (2002) ARKIVOC , vol.8 , pp. 112
- Sá, M.M.¹ Silveira, G.P.² Castilho, M.S.³ Pavão, F.⁴ Oliva, G.⁵

32
- 11144357543
- (b) Leitão, A.; Andricopulo, A. D.; Oliva, G.; Pupo, M. T.; de Marchi, A. A.; Vieira, P. C.; Silva, M. F. G. F.; Ferreira, V. F.; Souza, M. C. B. V.; Sa, M. M.; Morais, V. R. S.; Montanari, C. A. Bioorg. Med. Chem. Lett. 2004, 14, 2199.
- (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 2199
- Leitão, A.¹ Andricopulo, A.D.² Oliva, G.³ Pupo, M.T.⁴ de Marchi, A.A.⁵ Vieira, P.C.⁶ Silva, M.F.G.F.⁷ Ferreira, V.F.⁸ Souza, M.C.B.V.⁹ Sa, M.M.¹⁰ Morais, V.R.S.¹¹ Montanari, C.A.¹²

33
- 3042923841
- (a) Wallau, M.; Schuchardt, U. J. Braz. Chem. Soc. 1995, 6, 393.
- (1995) J. Braz. Chem. Soc , vol.6 , pp. 393
- Wallau, M.¹ Schuchardt, U.²

34
- 33645686467
- (b) Martins, L.; Cardoso, D. Quim. Nova 2006, 29, 358.
- (2006) Quim. Nova , vol.29 , pp. 358
- Martins, L.¹ Cardoso, D.²

35
- 0842309174
- (c) Kartha, K. P. R.; Mukhopadhyay, B.; Field, R. A. Carbohydr. Res. 2004, 339, 729.
- (2004) Carbohydr. Res , vol.339 , pp. 729
- Kartha, K.P.R.¹ Mukhopadhyay, B.² Field, R.A.³

36
- 33846511645
- Preparation of Potassium-Exchanged Molecular Sieves. A suspension of the appropriate molecular sieves (1.0 g) and 1 M KCl (10 mL) was stirred at r.t. for 15-18 h, followed by vacuum filtration and air-drying, obtaining a clear amorphous solid that can be stored for months without any special precautions. General Procedure for the Synthesis of Acetylated Nucleosides 1-10. Nucleoside (1.0 mmol, catalyst (0.6 g) and Ac2O (8-10 mmol) were stirred at 90-100 °C for the time indicated in Table 2. The final mixture was cooled to r.t, filtered, the catalyst was rinsed with CH 2Cl2, and the filtrate was concentrated under reduced pressure. The resulting residue was diluted in EtOAc and washed with sat. NaHCO3 and H2O. Then the aqueous phases were back-extracted with CH2Cl2 and the combined organic extracts were dried over Na2SO4, filtered and concentrated to give a solid residue
- 2O (8-10 mmol) and the catalyst (0.6 g) were placed in a 10 mL glass tube. The vessel was then sealed with a septum, placed into the microwave cavity and irradiated with stirring under the conditions presented in Table 3. After allowing the mixture to cool to r.t., the reaction vessel was opened and the contents were treated as above to give pure acetylated products after recrystallization.

37
- 33846489580
- Ikehara, M. Chem. Pharm. Bull. 1960, 8, 367.
- (1960) Chem. Pharm. Bull , vol.8 , pp. 367
- Ikehara, M.¹

38
- 0000978075
- Holmes, R. E.; Robins, R. K. J. Am. Chem. Soc. 1964, 86, 1242.
- (1964) J. Am. Chem. Soc , vol.86 , pp. 1242
- Holmes, R.E.¹ Robins, R.K.²

39
- 0342588747
- (a) Lewis, L. R.; Robins, R. K.; Cheng, C. C. J. Med. Chem. 1964, 7, 200.
- (1964) J. Med. Chem , vol.7 , pp. 200
- Lewis, L.R.¹ Robins, R.K.² Cheng, C.C.³

40
- 0013769518
- (b) Ikehara, M.; Uno, H.; Ishikawa, F. Chem. Pharm. Bull. 1964, 12, 267.
- (1964) Chem. Pharm. Bull , vol.12 , pp. 267
- Ikehara, M.¹ Uno, H.² Ishikawa, F.³

41
- 0028928475
- Saladino, R.; Crestini, C.; Occhionero, F.; Nicoletti, R. Tetrahedron 1995, 51, 3607.
- (1995) Tetrahedron , vol.51 , pp. 3607
- Saladino, R.¹ Crestini, C.² Occhionero, F.³ Nicoletti, R.⁴

42
- 17144461484
- Kuboki, A.; Ishihara, T.; Kobayashi, E.; Ohta, H.; Ishii, T.; Inoue, A.; Mitsuda, S.; Miyazaki, T.; Kajihara, Y.; Sugai, T. Biosci., Biotechnol., Biochem. 2000, 64, 363.
- (2000) Biosci., Biotechnol., Biochem , vol.64 , pp. 363
- Kuboki, A.¹ Ishihara, T.² Kobayashi, E.³ Ohta, H.⁴ Ishii, T.⁵ Inoue, A.⁶ Mitsuda, S.⁷ Miyazaki, T.⁸ Kajihara, Y.⁹ Sugai, T.¹⁰

43
- 0037100537
- Ciuffreda, P.; Loseto, A.; Santaniello, E. Tetrahedron 2002, 58, 5767.
- (2002) Tetrahedron , vol.58 , pp. 5767
- Ciuffreda, P.¹ Loseto, A.² Santaniello, E.³

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