메뉴 건너뛰기




Volumn 23, Issue 11, 2004, Pages 1723-1738

Efficient pyrimidine N-1-alkylation via activation of electron rich olefins with oxoammonium salts: Synthesis of Methoxy TEMPO substituted pyrimidine nucleoside analogs

Author keywords

2 substituted nucleoside analogs; Oxoammonium salts; Synthesis

Indexed keywords

ALKENE DERIVATIVE; AMMONIUM DERIVATIVE; OXOAMMONIUM; PYRIMIDINE NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 9644279551     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-200034038     Document Type: Article
Times cited : (8)

References (29)
  • 1
    • 0029585983 scopus 로고
    • Nitrogen glycosylation reactions involving pyrimidine and purine nucleoside bases with furanoside sugars
    • And references cited therein
    • Wilson, L.; Hager, M.; El-Kattam, Y.; Liotta, D. Nitrogen glycosylation reactions involving pyrimidine and purine nucleoside bases with furanoside sugars. Synthesis 1995, 12, 1465-1479. And references cited therein.
    • (1995) Synthesis , vol.12 , pp. 1465-1479
    • Wilson, L.1    Hager, M.2    El-Kattam, Y.3    Liotta, D.4
  • 2
    • 84982068675 scopus 로고
    • Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts
    • Vorbruggen, H.; Krolikiewicz, K.; Bennua, B. Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts. Chem. Ber. 1981, 114, 1234-1255.
    • (1981) Chem. Ber. , vol.114 , pp. 1234-1255
    • Vorbruggen, H.1    Krolikiewicz, K.2    Bennua, B.3
  • 3
    • 0016351762 scopus 로고
    • A general synthesis of N-glycosides. I. Synthesis of pyrimidine nucleosides
    • Niedballa, U.; Vorbruggen, H. A general synthesis of N-glycosides. I. Synthesis of pyrimidine nucleosides. J. Org. Chem. 1974, 39, 3654-3660.
    • (1974) J. Org. Chem. , vol.39 , pp. 3654-3660
    • Niedballa, U.1    Vorbruggen, H.2
  • 4
    • 0022381323 scopus 로고
    • Synthesis and optical properties of 2,3-dideoxy-D-erythro-hex-2- enopyranosyl nucleosides (nucleosides and nucleotides. LXII)
    • Ueda, T.; Watanabe, S. Synthesis and optical properties of 2,3-dideoxy-D-erythro-hex-2-enopyranosyl nucleosides (nucleosides and nucleotides. LXII). Chem. Pharm. Bull. 1985, 33, 3689-3695.
    • (1985) Chem. Pharm. Bull. , vol.33 , pp. 3689-3695
    • Ueda, T.1    Watanabe, S.2
  • 6
    • 0027238676 scopus 로고
    • Selenium controlled stereoselective synthesis of 2′deoxynucleosides from glycals. A formal synthesis of AZT
    • El-Laghdach, A.; Diaz, Y.; Castillon, S. Selenium controlled stereoselective synthesis of 2′deoxynucleosides from glycals. A formal synthesis of AZT. Tetrahedron Lett. 1993, 34, 2821-2822.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2821-2822
    • El-Laghdach, A.1    Diaz, Y.2    Castillon, S.3
  • 7
    • 0028050597 scopus 로고
    • Synthesis of 2′-deoxy-pyranosyl nucleosides from glycals through consecutive addition of phenylselenenyl chloride and glycosylation. A study of factors controlling the stereoselectivity
    • El-Laghdach, A.; Matheu, M.; Castillon, S. Synthesis of 2′-deoxy-pyranosyl nucleosides from glycals through consecutive addition of phenylselenenyl chloride and glycosylation. A study of factors controlling the stereoselectivity. Tetrahedron 1994, 50, 12219-12234.
    • (1994) Tetrahedron , vol.50 , pp. 12219-12234
    • El-Laghdach, A.1    Matheu, M.2    Castillon, S.3
  • 8
    • 0008461972 scopus 로고    scopus 로고
    • Adenosine nucleoside synthesis via electrophilic activation of electron rich alkenes
    • Stewart, D.; Trauth, J.; Windholtz, J.; Church, K. Adenosine nucleoside synthesis via electrophilic activation of electron rich alkenes. Synth. Commun. 1996, 26, 4279-4288.
    • (1996) Synth. Commun. , vol.26 , pp. 4279-4288
    • Stewart, D.1    Trauth, J.2    Windholtz, J.3    Church, K.4
  • 9
    • 0036181648 scopus 로고    scopus 로고
    • Amino-thiocyanation of electron rich olefins as an efficient purine and pyrimidine N-alkylation process
    • Chmielewski, J.; Haun, M.; Topmiller, K.; Ward, J.; Church, K. Amino-thiocyanation of electron rich olefins as an efficient purine and pyrimidine N-alkylation process. Synth. Commun. 2002, 32, 343-353.
    • (2002) Synth. Commun. , vol.32 , pp. 343-353
    • Chmielewski, J.1    Haun, M.2    Topmiller, K.3    Ward, J.4    Church, K.5
  • 10
    • 0000163993 scopus 로고
    • Oxidation of polymeric terminal diols with iron (III) or copper (II) salts mediated by the nitroxyl radical
    • Yoshida, E.; Takata, T.; Endo, T. Oxidation of polymeric terminal diols with iron (III) or copper (II) salts mediated by the nitroxyl radical. Macromolecules 1992, 25, 7282-7285.
    • (1992) Macromolecules , vol.25 , pp. 7282-7285
    • Yoshida, E.1    Takata, T.2    Endo, T.3
  • 11
    • 0035842129 scopus 로고    scopus 로고
    • Oxoammonium salts. Part 8: Oxidations in base: Oxidation of O-1 unprotected monosaccharides to lactones using 4-acetylamino-2,2,6,6- tetramethylpiperidine-1-oxoammonium tetrafluoroborate
    • Merbouh, N.; Bobbitt, J.; Bruckner, C. Oxoammonium salts. Part 8: oxidations in base: oxidation of O-1 unprotected monosaccharides to lactones using 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate. Tetrahedron Lett. 2001, 42, 8793-8796.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 8793-8796
    • Merbouh, N.1    Bobbitt, J.2    Bruckner, C.3
  • 12
    • 0032509230 scopus 로고    scopus 로고
    • Oxoammonium salts. 6. 4-Acetylamino-2,2,6,6-tetramethylpiperidine-1- oxoammonium perchlorate: A stable and convenient reagent for the oxidation of alcohols. Silica gel catalysis
    • Bobbitt, J. Oxoammonium salts. 6. 4-Acetylamino-2,2,6,6- tetramethylpiperidine-1-oxoammonium perchlorate: a stable and convenient reagent for the oxidation of alcohols. Silica gel catalysis. J. Org. Chem. 1998, 63, 9367-9374.
    • (1998) J. Org. Chem. , vol.63 , pp. 9367-9374
    • Bobbitt, J.1
  • 14
    • 0016326788 scopus 로고
    • A general synthesis of N-glycosides. II. Synthesis of 6-methyluridines
    • Niedballa, U.; Vorbruggen, H. A general synthesis of N-glycosides. II. Synthesis of 6-methyluridines. J. Org. Chem. 1974, 39, 3660.
    • (1974) J. Org. Chem. , vol.39 , pp. 3660
    • Niedballa, U.1    Vorbruggen, H.2
  • 15
    • 0017304337 scopus 로고
    • A general synthesis of N-Glycosides. 6. On the mechanism of the stannic chloride catalyzed Silyl-Hilbert-Johnson reaction
    • Niedballa, U.; Vorbruggen, H. A general synthesis of N-Glycosides. 6. On the mechanism of the stannic chloride catalyzed Silyl-Hilbert-Johnson reaction. J. Org. Chem. 1976, 41, 2084-2086.
    • (1976) J. Org. Chem. , vol.41 , pp. 2084-2086
    • Niedballa, U.1    Vorbruggen, H.2
  • 16
    • 0000939838 scopus 로고
    • The thermal decomposition of 1-(2′-cyano-2′-propoxy)-4-oxo-2, 2,6,6-tetramethylpiperidine
    • Grattan, D.; Carlsson, D.; Howard, J.; Wiles, D. The thermal decomposition of 1-(2′-cyano-2′-propoxy)-4-oxo-2,2,6,6- tetramethylpiperidine. Can. J. Chem. 1979, 57, 2834-2842.
    • (1979) Can. J. Chem. , vol.57 , pp. 2834-2842
    • Grattan, D.1    Carlsson, D.2    Howard, J.3    Wiles, D.4
  • 17
    • 0029936835 scopus 로고    scopus 로고
    • Definitive solution structures for the 6-formylated versions of 1-(β-D-ribofuranosyl)-, 1-(2′-deoxy-β-D-ribofuranosyl)-, and 1-(β-D-arabinofuranosyluracil, and of thymidine
    • Groziak, M.; Lin, R.; Stevens, W.; Wotring, L.; Townsend, L.; Balzarini, J.; Witvrouw, M.; De Clerq, E. Definitive solution structures for the 6-formylated versions of 1-(β-D-ribofuranosyl)-, 1-(2′-deoxy-β- D-ribofuranosyl)-, and 1-(β-D-arabinofuranosyluracil, and of thymidine. Nucleosides and Nucleotides 1996, 15, 1041-1057.
    • (1996) Nucleosides and Nucleotides , vol.15 , pp. 1041-1057
    • Groziak, M.1    Lin, R.2    Stevens, W.3    Wotring, L.4    Townsend, L.5    Balzarini, J.6    Witvrouw, M.7    De Clerq, E.8
  • 18
    • 0036272242 scopus 로고    scopus 로고
    • Synthesis and pairing properties of 3′-deoxyribopyranose (4′-2′)-oligonucleotides ('p-DNA)
    • Ackermann, D.; Pitsch, S. Synthesis and pairing properties of 3′-deoxyribopyranose (4′-2′)-oligonucleotides ('p-DNA). Helv. Chim. Acta 2002, 85, 1443-1462.
    • (2002) Helv. Chim. Acta , vol.85 , pp. 1443-1462
    • Ackermann, D.1    Pitsch, S.2
  • 19
    • 9644292456 scopus 로고
    • Nucleosides. 118. Total synthesis of pentopyranin B and D. Cytosine nucleosides elaborated by streptomyces griseochromogenes
    • Watanabe, K.; Matsuda, A.; Itoh, T. Nucleosides. 118. Total synthesis of pentopyranin B and D. Cytosine nucleosides elaborated by streptomyces griseochromogenes. Can. J. Chem. 1981, 59, 468-472.
    • (1981) Can. J. Chem. , vol.59 , pp. 468-472
    • Watanabe, K.1    Matsuda, A.2    Itoh, T.3
  • 20
    • 0026641180 scopus 로고
    • Incorporation of hexose nucleoside analogues into oligonucleotides: Synthesis, base pairing properties and enzymatic stability
    • Augustyns, K.; Vandendriessche, F.; Van Aersehot, A.; Busson, R.; Urbanke, C.; Herdewijn, P. Incorporation of hexose nucleoside analogues into oligonucleotides: synthesis, base pairing properties and enzymatic stability. Nucleic Acids Res. 1992, 20(18), 4711-4716.
    • (1992) Nucleic Acids Res. , vol.20 , Issue.18 , pp. 4711-4716
    • Augustyns, K.1    Vandendriessche, F.2    Van Aersehot, A.3    Busson, R.4    Urbanke, C.5    Herdewijn, P.6
  • 21
    • 0018680588 scopus 로고
    • Synthesis and biological activities of ftorafur metabolites. 3′- and 4′-hydroxyftorafur
    • Lin, A.; Benjamin, R.; Rao, P.; Loo, T. Synthesis and biological activities of ftorafur metabolites. 3′- and 4′-hydroxyftorafur. J. Med. Chem. 1979, 22 (9), 1096-1100.
    • (1979) J. Med. Chem. , vol.22 , Issue.9 , pp. 1096-1100
    • Lin, A.1    Benjamin, R.2    Rao, P.3    Loo, T.4
  • 22
    • 0020025295 scopus 로고
    • Studies on antitumor agents. IV. Synthesis and antitumor activities of compounds related to 1-(tetrahydro-2-furanyl)-5-fluorouracil metabolites
    • Ueda, S.; Takeda, S.; Yamawaki, I.; Yamashita, J.; Yasumoto, M.; Hashimoto, S. Studies on antitumor agents. IV. Synthesis and antitumor activities of compounds related to 1-(tetrahydro-2-furanyl)-5-fluorouracil metabolites. Chem. Pharm. Bull. 1982, 30(1), 125-131.
    • (1982) Chem. Pharm. Bull. , vol.30 , Issue.1 , pp. 125-131
    • Ueda, S.1    Takeda, S.2    Yamawaki, I.3    Yamashita, J.4    Yasumoto, M.5    Hashimoto, S.6
  • 24
    • 0029077840 scopus 로고
    • Characterization of fully 2′-modified oligoribonucleotide hetero- and homoduplex hybridization and nuclease sensitivity
    • Cummins, L.; Owens, S.; Risen, L.; Lesnik, E.; Freier, S.; McGee, D.; Guinosso, C.; Cook, P. Characterization of fully 2′-modified oligoribonucleotide hetero- and homoduplex hybridization and nuclease sensitivity. Nucleic Acids Res. 1995, 23, 2019-2024.
    • (1995) Nucleic Acids Res. , vol.23 , pp. 2019-2024
    • Cummins, L.1    Owens, S.2    Risen, L.3    Lesnik, E.4    Freier, S.5    McGee, D.6    Guinosso, C.7    Cook, P.8
  • 25
    • 0342961064 scopus 로고    scopus 로고
    • Synthesis of 3′-deoxy-3′diflouromethyluridine and 2′-deoxy-2′-diflouromethyluridine
    • Marcotte, S.; Gerard, B.; Pannecoucke, X.; Feasson, C.; Quirion, J. Synthesis of 3′-deoxy-3′diflouromethyluridine and 2′-deoxy-2′-diflouromethyluridine. Synthesis 2001, 6, 929-933.
    • (2001) Synthesis , vol.6 , pp. 929-933
    • Marcotte, S.1    Gerard, B.2    Pannecoucke, X.3    Feasson, C.4    Quirion, J.5
  • 26
    • 0015913888 scopus 로고
    • Conformational analysis of the sugar ring in nucleosides and nucleotides. Improved method for the interpretation of proton magnetic resonance coupling constants
    • Altona, C.; Sundaralingam, M. Conformational analysis of the sugar ring in nucleosides and nucleotides. Improved method for the interpretation of proton magnetic resonance coupling constants. J. Am. Chem. Soc. 1973, 95, 2333-2344.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 2333-2344
    • Altona, C.1    Sundaralingam, M.2
  • 27
    • 0002067641 scopus 로고    scopus 로고
    • Synthesis and conformation of 3′-O, 4′-C- methyleneribonucleosides, novel bicyclic nucleoside analogues for 2′,5′-linked oligonucleotide modification
    • Obika, S.; Morio, K.; Nanbu, D.; Imanishi, T. Synthesis and conformation of 3′-O, 4′-C-methyleneribonucleosides, novel bicyclic nucleoside analogues for 2′,5′-linked oligonucleotide modification. Chem. Commun. 1997, 1643-1644.
    • (1997) Chem. Commun. , pp. 1643-1644
    • Obika, S.1    Morio, K.2    Nanbu, D.3    Imanishi, T.4
  • 28
    • 0008270863 scopus 로고
    • Stereoselection in acyclic systems. The synthesis of amino sugars via nitrone cycloadditions
    • DeShong, P.; Dicken, C.; Leginus, J.; Whittle, R. Stereoselection in acyclic systems. The synthesis of amino sugars via nitrone cycloadditions. J. Am. Chem. Soc. 1984, 106, 5598-5602.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 5598-5602
    • DeShong, P.1    Dicken, C.2    Leginus, J.3    Whittle, R.4
  • 29
    • 0001679530 scopus 로고
    • Enantiogenic total synthesis of (-)-indolizidines (bicyclic gephyrotoxins) 205A, 207A, 209B and 235 B via the intramolecular Diels-Alder reaction of a chiral N-acylnitroso compound
    • Shishido, Y.; Kibayashi, C. Enantiogenic total synthesis of (-)-indolizidines (bicyclic gephyrotoxins) 205A, 207A, 209B and 235 B via the intramolecular Diels-Alder reaction of a chiral N-acylnitroso compound. J. Org. Chem. 1992, 57, 2876-2883.
    • (1992) J. Org. Chem. , vol.57 , pp. 2876-2883
    • Shishido, Y.1    Kibayashi, C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.