Synthesis of new iso-C-nucleoside analogues from 2-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)ethanal

Carbohydrate Research

Volumn 340, Issue 4, 2005, Pages 547-555

  Otero, Iran ^a,b   Feist, Holger ^a   Herrera, Lidcay ^a   Michalik, Manfred ^a   Quincoces, José ^c   Peseke, Klaus ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b CENTRAL UNIVERSITY OF LAS VILLAS   (Cuba)

^c Universidade Bandeirante de Sao Paulo   (Brazil)

Author keywords

Branched chain monosaccharides; Iso C nucleosides; Nucleoside analogues; Thieno 2.3 d pyrimidines; Thiophenecarbonic acid derivatives

Indexed keywords

ALUMINA; DERIVATIVES; INORGANIC ACIDS; NITROGEN COMPOUNDS; SULFUR; SYNTHESIS (CHEMICAL);

DEPROTECTION; MALONITRILES; PYRIMIDINE;

AROMATIC COMPOUNDS;

2 (METHYL 2 O BENZYL 4,6 O BENZYLIDENE 3 DEOXY ALPHA DEXTRO ALTROPYRANOSID 3 YL)ETHANAL; 2 AMINO 5 (1,6 ANHYDRO 3 DEOXY BETA DEXTRO ALTROPYRANOS 3 YL)THIOPHENE 3 CARBONITRILE; 2 AMINO 5 (METHYL 2 O BENZYL 3 DEOXY ALPHA DEXTRO ALTROPYRANOSID 3 YL)THIOPHENE 3 CARBONITRILE; 3,4 DIHYDRO 3 (4 METHOXYPHENYL) 6 (METHYL 2 O BENZYL 4,6 O BENZYLIDENE 3 DEOXY ALPHA DEXTRO ALTROPYRANOSID 3 YL)THIENO[2,3 D]PYRIMIDIN 4 ONE; 3,4 DIHYDRO 6 (1,6 ANHYDRO 3 DEOXY BETA DEXTRO ALTROPYRANOS 3 YL)THIENO[2,3 D]PYRIMIDIN 4 ONE; 3,4 DIHYDRO 6 (METHYL 2 O BENZYL 3 DEOXY ALPHA DEXTRO ALTROPYRANOSID 3 YL)THIENO[2,3 D]PYRIMIDIN 4 ONE; 3,4 DIHYDRO 6 (METHYL 2 O BENZYL 4,6 O BENZYLIDENE 3 DEOXY ALPHA DEXTRO ALTROPYRANOSID 3 YL)THIENO[2,3 D]PYRIMIDIN 4 ONE; 4 AMINO 5 (METHYL 2 O BENZYL 3 DEOXY ALPHA DEXTRO ALTROPYRANOSID 3 YL)THIENO[2,3 D]PYRIMIDINE; 4 AMINO 6 (1,6 ANHYDRO 3 DEOXY BETA DEXTRO ALTROPYRANOS 3 YL)THIENO[2,3 D]PYRIMIDINE; 4 AMINO 6 (METHYL 2 O BENZYL 4,6 O BENZYLIDENE 3 DEOXY ALPHA DEXTRO ALTROPYRANOSID 3 YL)THIENO[2,3 D]PYRIMIDINE; ACETAMIDE DERIVATIVE; ALUMINUM OXIDE; AMMONIA; BENZYLIDENE DERIVATIVE; CARBONIC ACID DERIVATIVE; CROTONIC ACID DERIVATIVE; FORMIC ACID DERIVATIVE; MALONONITRILE; NUCLEOSIDE DERIVATIVE; PYRIMIDINE DERIVATIVE; SULFUR; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYCLIZATION; DEPROTECTION REACTION; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ALUMINUM OXIDE; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; GLYCOSIDES; MOLECULAR STRUCTURE; NITRILES; NUCLEOSIDES; PYRIMIDINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR;

EID: 13844318807     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2005.01.003     Document Type: Article

References (36)

1. U.S. Pathak, R.S. Patel, and S. Singh Ind. J. Pharm. Sci. 53 1991 85 87
2. L. Huybrechts, D. Buffel, E. Freyne, and G. Hoornaert Tetrahedron 40 1984 2479 2485
3. Y.A. Ibrahim, A.H.M. Elwahy, and A.M. Kadry Adv. Heterocycl. Chem. 65 1996 235 281
4. R.K. Russell, J.B. Press, R.A. Rampulla, J.J. McNally, R. Falotico, J.A. Keiser, D.A. Bright, and A. Tobia J. Med. Chem. 31 1988 1786 1793
5. D.L. Temple, J.P. Yevich, R.R. Covington, C.A. Hanning, R.J. Seidehamel, H.K. Mackey, and M.J. Bartek J. Med. Chem. 22 1979 505 510
6. I.A. Shehata, H.I. El-Subbagh, A.M. Abdelal, M.A. El-Sherbeny, and A.A. Al-Obaid Med. Chem. Res. 6 1996 148 163
7. U.S. Pathak, S. Singh, and Padh Indian J. Chem., Sect. B 30B 1991 618 619
8. A.A. El-Barbary, N.R. El-Brollosy, E.B. Pedersen, and C. Nielsen Monatsh. Chem. 126 1995 593 600
9. A.A. El-Barbary, R. El-Brollosy, E.B. Pedersen, and C. Nielsen Sulfur Lett. 20 1996 31 42
10. A.A. El-Barbary, N.R. El-Brollosy, H.M. Abdel-Bary, E.B. Pedersen, P. Stein, and C. Nielsen Liebigs Ann. Chem. 1995 1371 1375
11. V.D. Patil, D.S. Wise, L.L. Wotring, L.C. Bloomer, and L.B. Townsend J. Med. Chem. 28 1985 423 427
12. C. Simons C-Nucleosides C. Simons Nucleoside Mimetics: Their Chemistry and Biological Properties 2001 Harwood Academic Amsterdam 117 135
13. H.W. Yu, H.Y. Zhang, Z.J. Yang, J.M. Min, L.T. Ma, and L.H. Zhang Pure Appl. Chem. 70 1998 435 438
14. M. Zhang, H. Zhang, Z. Yang, L. Ma, J. Min, and L. Zhang Carbohydr. Res. 318 1999 157 161
15. G. Casiraghi, M. Cornia, G. Rassu, C.D. Sante, and P. Spanu Tetrahedron 48 1992 5619 5628
16. K. Gewald, M. Kleinert, B. Thiele, and M. Hentschel J. Prakt. Chem. 314 1972 303 314
17. M. Gómez, J. Quincoces, K. Peseke, M. Michalik, and H.J. Reinke J. Carbohydr. Chem. 18 1999 851 865
18. I. Garcia, H. Feist, R. Cao, M. Michalik, and K.J. Peseke Carbohydr. Chem. 20 2001 681 687
19. L. Herrera, H. Feist, J. Quincoces, M. Michalik, and K. Peseke J. Carbohydr. Chem. 22 2003 171 178
20. A.B. Hughes, R.V. Stick, and D.M. Tilbrook Aust. J. Chem. 43 1990 1681 1695
21. A.J. Wood, D.J. Holt, M. Domínguez, and P.R. Jenkins J. Org. Chem. 63 1998 8522 8529
22. A. Fürstner, and J. Baumgartner Tetrahedron 49 1993 8541 8560
23. M. Nakata, K. Toshima, T. Kai, and M. Kinoshita Bull. Chem. Soc. Jpn. 58 1985 3457 3464
24. M.H.D. Postema, J.L. Piper, L. Liu, J. Shen, M. Faust, and P. Andreana J. Org. Chem. 68 2003 4748 4754
25. J.M.J. Tronchet, M. Zsély, and M. Geoffroy Carbohydr. Res. 275 1995 245 258
26. K. Peseke, H. Feist, W. Hanefeld, J. Kopf, and H. Schulz J. Carbohydr. Chem. 14 1995 317 325
27. F. Texier-Boullet, and A. Focaud Tetrahedron Lett. 23 1982 4727 4728
28. E.C. Taylor, and J. Berger J. Org. Chem. 32 1967 2376 2378
29. M.E. Jung, and M.A. Lyster J. Org. Chem. 42 1977 3761 3764
30. G.A. Olah, S.C. Narang, B.G. Gupta, and R. Malhotra J. Org. Chem. 44 1979 1247 1251
31. T.H. Chan, and S.D. Lee Tetrahedron Lett. 24 1983 1225 1228
32. A. Millar, K. Kim, D. Minster, T. Ohgi, and S. Hecht J. Org. Chem. 51 1986 189 196
33. F. Yamazaki, S. Sato, T. Nukada, Y. Ito, and T. Ogawa Carbohydr. Res. 201 1990 31 50
34. C. Cruzado, and M. Martin-Lomas Carbohydr. Res. 175 1988 193 199
35. R. Rijsbergen, M. Anteunis, and A. De Bruyn J. Carbohydr. Chem. 11 1992 463 470
36. H. Paulsen, V. Sinnwell, and W. Greve Carbohydr. Res. 49 1976 27 35