SCOPUS 정보 검색 플랫폼

Tetrahedron

Volumn 54, Issue 23, 1998, Pages 6445-6456

Synthesis of difluorocyclopropyl carbocyclic homo-nucleosides

(2) Csuk, René a Eversmann, Leo a

a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4 BENZYLOXY 2 BUTENYL ACETATE; ACETIC ACID; DIFLUOROCYCLOPROPYL CARBOCYCLIC HOMO NUCLEOSIDE; FLUOROURACIL DERIVATIVE; NUCLEOSIDE ANALOG; SODIUM DIFLUOROACETATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032482299 PISSN: 00404020 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4020(98)00324-X Document Type: Article

Times cited : (64)

References (46)

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14
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15
- 0029815591
- 6-Chloro-purine has previously been used in Mitsunobu reactions, cf.
- 10 6-Chloro-purine has previously been used in Mitsunobu reactions, cf. Rosenquist, A.; Kvarnstroem, I.; Classon, B.; Samuelsson, B. J. Org. Chem. 1996, 61, 6282-6288; Andersen, M. W.; Daluge, S. M.;Kerremans, L.; Herdewijn, P. Tetrahedron Lett. 1996, 37, 8147-8150; Chen, W.; Flavin, M. T.; Filler,R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978; Capretta, A.; Bell, R. A. Can. J. Chem. 1995,73, 2224-2232; Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Mitsuya, H.; Barchi, J. J. J. Med.Chem. 1994, 37, 3389-3399; Roberts, S. M.; Shoberu, K. A. J. Chem. Soc. Perkin Trans 1 1991, 2605-2607.
- (1996) J. Org. Chem. , vol.61 , pp. 6282-6288
- Rosenquist, A.¹ Kvarnstroem, I.² Classon, B.³ Samuelsson, B.⁴

16
- 0030569264
- 10 6-Chloro-purine has previously been used in Mitsunobu reactions, cf. Rosenquist, A.; Kvarnstroem, I.;Classon, B.; Samuelsson, B. J. Org. Chem. 1996, 61, 6282-6288; Andersen, M. W.; Daluge, S. M.; Kerremans, L.; Herdewijn, P. Tetrahedron Lett. 1996, 37, 8147-8150; Chen, W.; Flavin, M. T.; Filler,R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978; Capretta, A.; Bell, R. A. Can. J. Chem. 1995,73, 2224-2232; Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Mitsuya, H.; Barchi, J. J. J. Med.Chem. 1994, 37, 3389-3399; Roberts, S. M.; Shoberu, K. A. J. Chem. Soc. Perkin Trans 1 1991, 2605-2607.
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- Andersen, M.W.¹ Daluge, S.M.² Kerremans, L.³ Herdewijn, P.⁴

17
- 0029840981
- 10 6-Chloro-purine has previously been used in Mitsunobu reactions, cf. Rosenquist, A.; Kvarnstroem, I.;Classon, B.; Samuelsson, B. J. Org. Chem. 1996, 61, 6282-6288; Andersen, M. W.; Daluge, S. M.;Kerremans, L.; Herdewijn, P. Tetrahedron Lett. 1996, 37, 8147-8150; Chen, W.; Flavin, M. T.; Filler, R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978; Capretta, A.; Bell, R. A. Can. J. Chem. 1995,73, 2224-2232; Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Mitsuya, H.; Barchi, J. J. J. Med.Chem. 1994, 37, 3389-3399; Roberts, S. M.; Shoberu, K. A. J. Chem. Soc. Perkin Trans 1 1991, 2605-2607.
- (1996) Tetrahedron Lett. , vol.37 , pp. 8975-8978
- Chen, W.¹ Flavin, M.T.² Filler, R.³ Xu, Z.-Q.⁴

18
- 0010339123
- 10 6-Chloro-purine has previously been used in Mitsunobu reactions, cf. Rosenquist, A.; Kvarnstroem, I.;Classon, B.; Samuelsson, B. J. Org. Chem. 1996, 61, 6282-6288; Andersen, M. W.; Daluge, S. M.;Kerremans, L.; Herdewijn, P. Tetrahedron Lett. 1996, 37, 8147-8150; Chen, W.; Flavin, M. T.; Filler,R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978; Capretta, A.; Bell, R. A. Can. J. Chem. 1995, 73, 2224-2232; Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Mitsuya, H.; Barchi, J. J. J. Med.Chem. 1994, 37, 3389-3399; Roberts, S. M.; Shoberu, K. A. J. Chem. Soc. Perkin Trans 1 1991, 2605-2607.
- (1995) Can. J. Chem. , vol.73 , pp. 2224-2232
- Capretta, A.¹ Bell, R.A.²

19
- 0028004592
- 10 6-Chloro-purine has previously been used in Mitsunobu reactions, cf. Rosenquist, A.; Kvarnstroem, I.;Classon, B.; Samuelsson, B. J. Org. Chem. 1996, 61, 6282-6288; Andersen, M. W.; Daluge, S. M.;Kerremans, L.; Herdewijn, P. Tetrahedron Lett. 1996, 37, 8147-8150; Chen, W.; Flavin, M. T.; Filler,R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978; Capretta, A.; Bell, R. A. Can. J. Chem. 1995,73, 2224-2232; Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Mitsuya, H.; Barchi, J. J. J. Med. Chem. 1994, 37, 3389-3399; Roberts, S. M.; Shoberu, K. A. J. Chem. Soc. Perkin Trans 1 1991, 2605-2607.
- (1994) J. Med. Chem. , vol.37 , pp. 3389-3399
- Rodriguez, J.B.¹ Marquez, V.E.² Nicklaus, M.C.³ Mitsuya, H.⁴ Barchi, J.J.⁵

20
- 37049088949
- 10 6-Chloro-purine has previously been used in Mitsunobu reactions, cf. Rosenquist, A.; Kvarnstroem, I.;Classon, B.; Samuelsson, B. J. Org. Chem. 1996, 61, 6282-6288; Andersen, M. W.; Daluge, S. M.;Kerremans, L.; Herdewijn, P. Tetrahedron Lett. 1996, 37, 8147-8150; Chen, W.; Flavin, M. T.; Filler,R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978; Capretta, A.; Bell, R. A. Can. J. Chem. 1995,73, 2224-2232; Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Mitsuya, H.; Barchi, J. J. J. Med.Chem. 1994, 37, 3389-3399; Roberts, S. M.; Shoberu, K. A. J. Chem. Soc. Perkin Trans 1 1991, 2605-2607.
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- Roberts, S.M.¹ Shoberu, K.A.²

21
- 0010382490
- 19F NMR spectroscopy no isomerizations at the cyclopropane unity took place under these conditions
- 19F NMR spectroscopy no isomerizations at the cyclopropane unity took place under these conditions.

22
- 0000218303
- N-Benzoyl-thymine (3-benzoyl-5-methyl-1H-pyrimidine-2,4-dione) was obtained by benzoylation of thymine with benzoyl chloride/pyridine for 2 h at 80°C in 40-50% yield after recrystallization from ethanol; mp 215-217 °C lit.: 215 °C
- 2: 230.0691; found: 230.0692.
- (1965) Coll. Czech. Chem. Commun. , vol.30 , pp. 1890-1899
- Novacek, A.¹ Hesoun, D.² Gut, J.³

23
- 48749141566
- interestingly enough, a strongly deviating mp of 150-152°C has been reported for this material by
- 2: 230.0691; found: 230.0692.
- (1984) Tetrahedron Lett. , vol.25 , pp. 681-684
- Cruickshank, K.A.¹ Jiricny, J.² Reese, C.B.³

24
- 0010379807
- note
- 2: 230.0691; found: 230.0692.

25
- 0026042876
- 13 Previously used in Mitsunobu reactions, cf. Jenny, T. F.; Previsani, N.; Benner, S. A. Tetrahedron Lett. 1991, 32, 7029-7032; Hossain, N.; Rozenski, J.; De Clercq, E.; Herdewijn, P. J. Org. Chem.1997, 62, 2442-2447; Alexander, P.; Krishnamurty, V. V.; Prisbe, E. J. J. Med. Chem. 1996, 39, 1321-1330; Drake, A. F.; Garofalo, A.; Hillman, J. M. L.; Merlo, V.; McCague, R.; Roberts, S. M. J. Chem.Soc. Perkin Trans 1 1996, 2739-2746.
- (1991) Tetrahedron Lett. , vol.32 , pp. 7029-7032
- Jenny, T.F.¹ Previsani, N.² Benner, S.A.³

26
- 0030965348
- 13 Previously used in Mitsunobu reactions, cf. Jenny, T. F.; Previsani, N.; Benner, S. A. TetrahedronLett. 1991, 32, 7029-7032; Hossain, N.; Rozenski, J.; De Clercq, E.; Herdewijn, P. J. Org. Chem. 1997, 62, 2442-2447; Alexander, P.; Krishnamurty, V. V.; Prisbe, E. J. J. Med. Chem. 1996, 39, 1321-1330; Drake, A. F.; Garofalo, A.; Hillman, J. M. L.; Merlo, V.; McCague, R.; Roberts, S. M. J. Chem.Soc. Perkin Trans 1 1996, 2739-2746.
- (1997) J. Org. Chem. , vol.62 , pp. 2442-2447
- Hossain, N.¹ Rozenski, J.² De Clercq, E.³ Herdewijn, P.⁴

27
- 0029944529
- 13 Previously used in Mitsunobu reactions, cf. Jenny, T. F.; Previsani, N.; Benner, S. A. TetrahedronLett. 1991, 32, 7029-7032; Hossain, N.; Rozenski, J.; De Clercq, E.; Herdewijn, P. J. Org. Chem.1997, 62, 2442-2447; Alexander, P.; Krishnamurty, V. V.; Prisbe, E. J. J. Med. Chem. 1996, 39, 1321-1330; Drake, A. F.; Garofalo, A.; Hillman, J. M. L.; Merlo, V.; McCague, R.; Roberts, S. M. J. Chem.Soc. Perkin Trans 1 1996, 2739-2746.
- (1996) J. Med. Chem. , vol.39 , pp. 1321-1330
- Alexander, P.¹ Krishnamurty, V.V.² Prisbe, E.J.³

28
- 0002367933
- 13 Previously used in Mitsunobu reactions, cf. Jenny, T. F.; Previsani, N.; Benner, S. A. TetrahedronLett. 1991, 32, 7029-7032; Hossain, N.; Rozenski, J.; De Clercq, E.; Herdewijn, P. J. Org. Chem.1997, 62, 2442-2447; Alexander, P.; Krishnamurty, V. V.; Prisbe, E. J. J. Med. Chem. 1996, 39, 1321-1330; Drake, A. F.; Garofalo, A.; Hillman, J. M. L.; Merlo, V.; McCague, R.; Roberts, S. M. J. Chem. Soc. Perkin Trans 1 1996, 2739-2746.
- (1996) J. Chem. Soc. Perkin Trans , vol.1 , pp. 2739-2746
- Drake, A.F.¹ Garofalo, A.² Hillman, J.M.L.³ Merlo, V.⁴ McCague, R.⁵ Roberts, S.M.⁶

29
- 48749141566
- 3 in dioxane/water and showed a mp 202-215°C (lit.: mp 148-149°C by
- 2: 216.0534; found: 216.0535. It has previously been used in Mitsunobu reactions, cf.Altman, K.-H.; Schmit-Chiese, C.; Garcia-Echeverria, C. Bioorg. Med. Chem. Lett. 1977, 7, 1119-1122; Capaldi, D. C.; Eleuteri, A.; Chen, Q.; Schinanzi, R. F. Nucleosides Nucleotides 1997,16, 403-416; Perez-Perez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn J. Org. Chem. 1995, 60, 1531-1537.
- (1984) Tetrahedron Lett. , vol.25 , pp. 681-684
- Cruickshank, K.A.¹ Jiricny, J.² Reese, C.B.³

30
- 0000218303
- 200-202°C by
- 2: 216.0534; found: 216.0535. It has previously been used in Mitsunobu reactions, cf.Altman, K.-H.; Schmit-Chiese, C.; Garcia-Echeverria, C. Bioorg. Med. Chem. Lett. 1977, 7, 1119-1122; Capaldi, D. C.; Eleuteri, A.; Chen, Q.; Schinanzi, R. F. Nucleosides Nucleotides 1997,16, 403-416; Perez-Perez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn J. Org. Chem. 1995, 60, 1531-1537.
- (1965) Coll. Czech. Chem. Commun. , vol.30 , pp. 1890-1899
- Novacek, A.¹ Hesoun, D.² Gut, J.³

31
- 0014275246
- 216°C by
- 2: 216.0534; found: 216.0535. It has previously been used in Mitsunobu reactions, cf.Altman, K.-H.; Schmit-Chiese, C.; Garcia-Echeverria, C. Bioorg. Med. Chem. Lett. 1977, 7, 1119-1122; Capaldi, D. C.; Eleuteri, A.; Chen, Q.; Schinanzi, R. F. Nucleosides Nucleotides 1997,16, 403-416; Perez-Perez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn J. Org. Chem. 1995, 60, 1531-1537.
- (1968) J. Org. Chem. , vol.33 , pp. 1341
- Pitha, P.¹

32
- 0343852708
- note
- 2: 216.0534; found: 216.0535. It has previously been used in Mitsunobu reactions, cf. Altman, K.-H.; Schmit-Chiese, C.; Garcia-Echeverria, C. Bioorg. Med. Chem. Lett. 1977, 7, 1119-1122; Capaldi, D. C.; Eleuteri, A.; Chen, Q.; Schinanzi, R. F. Nucleosides Nucleotides 1997,16, 403-416; Perez-Perez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn J. Org. Chem. 1995, 60, 1531-1537.
- (1977) Bioorg. Med. Chem. Lett. , vol.7 , pp. 1119-1122
- Altman, K.-H.¹ Schmit-Chiese, C.² Garcia-Echeverria, C.³

33
- 0030988278
- 2: 216.0534; found: 216.0535. It has previously been used in Mitsunobu reactions, cf.Altman, K.-H.; Schmit-Chiese, C.; Garcia-Echeverria, C. Bioorg. Med. Chem. Lett. 1977, 7, 1119-1122; Capaldi, D. C.; Eleuteri, A.; Chen, Q.; Schinanzi, R. F. Nucleosides Nucleotides 1997,16, 403-416; Perez-Perez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn J. Org. Chem. 1995, 60, 1531-1537.
- (1997) Nucleosides Nucleotides , vol.16 , pp. 403-416
- Capaldi, D.C.¹ Eleuteri, A.² Chen, Q.³ Schinanzi, R.F.⁴

34
- 0028931482
- 2: 216.0534; found: 216.0535. It has previously been used in Mitsunobu reactions, cf.Altman, K.-H.; Schmit-Chiese, C.; Garcia-Echeverria, C. Bioorg. Med. Chem. Lett. 1977, 7, 1119-1122; Capaldi, D. C.; Eleuteri, A.; Chen, Q.; Schinanzi, R. F. Nucleosides Nucleotides 1997,16, 403-416; Perez-Perez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn J. Org. Chem. 1995, 60, 1531-1537.
- (1995) J. Org. Chem. , vol.60 , pp. 1531-1537
- Perez-Perez, M.-J.¹ Rozenski, J.² Busson, R.³ Herdewijn⁴

35
- 0029063347
- 15 Kalinichenko, E.N.; Rubinova, E. B.; Borisov, E. V.; Balzarini, J.; De Clercq, E.; Mikhailogulo, I. A. Nucleosides Nucleotides 1995, 14, 533-536; Perez-Perez, M.-J.; San-Felix, A.; Balzarini, J.; De Clercq,E.; Camarasa, M. J. J. Med. Chem. 1992, 35, 2988-2995; Sells, T. B. Nair, V. Tetrahedron 1994, 50,117-138.
- (1995) Nucleosides Nucleotides , vol.14 , pp. 533-536
- Kalinichenko, E.N.¹ Rubinova, E.B.² Borisov, E.V.³ Balzarini, J.⁴ De Clercq, E.⁵ Mikhailogulo, I.A.⁶

36
- 0026737678
- 15 Kalinichenko, E.N.; Rubinova, E. B.; Borisov, E. V.; Balzarini, J.; De Clercq, E.; Mikhailogulo, I. A.Nucleosides Nucleotides 1995, 14, 533-536; Perez-Perez, M.-J.; San-Felix, A.; Balzarini, J.; De Clercq, E.; Camarasa, M. J. J. Med. Chem. 1992, 35, 2988-2995; Sells, T. B. Nair, V. Tetrahedron 1994, 50,117-138.
- (1992) J. Med. Chem. , vol.35 , pp. 2988-2995
- Perez-Perez, M.-J.¹ San-Felix, A.² Balzarini, J.³ De Clercq, E.⁴ Camarasa, M.J.⁵

37
- 0028152276
- 15 Kalinichenko, E.N.; Rubinova, E. B.; Borisov, E. V.; Balzarini, J.; De Clercq, E.; Mikhailogulo, I. A.Nucleosides Nucleotides 1995, 14, 533-536; Perez-Perez, M.-J.; San-Felix, A.; Balzarini, J.; De Clercq,E.; Camarasa, M. J. J. Med. Chem. 1992, 35, 2988-2995; Sells, T. B. Nair, V. Tetrahedron 1994, 50, 117-138.
- (1994) Tetrahedron , vol.50 , pp. 117-138
- Sells, T.B.¹ Nair, V.²

38
- 0030921946
- 16 Gourdel-Martin, M.-E.; Huet, F. J. Org. Chem. 1997, 62, 2166-2172.
- (1997) Org. Chem. , vol.62 , pp. 2166-2172
- Gourdel-Martin, M.-E.¹ Huet, F.J.²

39
- 37049073521
- N-Benzoyl-5-fluoro-uracil (3-benzoyl-5-fluoro-1H-pyrimidine-2,4-dione) was obtained by benzoylation of 5-fluoro-uracil with benzoyl chloride/pyridine for 1h and showed a mp 163-165°C
- 3F: 234.0440; found: 234.0441; previously used in Mitsunobu reactions: Verheggen, I.; Van Aerschat, A.; Van Meervelt, L.; Rozenski, J.; Wiebe, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1995, 38, 826-835.
- (1990) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 795-802
- Lucey, N.M.¹ McCormick, J.E.² McElhinney, R.S.³

40
- 0020434708
- lit.: 148-152
- 3F: 234.0440; found: 234.0441; previously used in Mitsunobu reactions: Verheggen, I.; Van Aerschat, A.; Van Meervelt, L.; Rozenski, J.; Wiebe, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1995, 38, 826-835.
- (1982) Chem. Pharm. Bull , vol.30 , pp. 4258-4267
- Yamashita, J.-I.¹ Yamawaki, I.² Ueda, S.³ Yasumoto, M.⁴ Unemi, N.⁵ Hashimoto, S.⁶

41
- 0028930270
- mp 165-167 vide supra or mp 170°C
- 3F: 234.0440; found: 234.0441; previously used in Mitsunobu reactions: Verheggen, I.; Van Aerschat, A.; Van Meervelt, L.; Rozenski, J.; Wiebe, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1995, 38, 826-835.
- Lucey, N.M.¹

42
- 0028930270
- 2602175
- 3F: 234.0440; found: 234.0441; previously used in Mitsunobu reactions: Verheggen, I.; Van Aerschat, A.; Van Meervelt, L.; Rozenski, J.; Wiebe, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1995, 38, 826-835.
- Ger. Offen.
- Ishida, T.¹ Nishimura, D.² Sugawara, T.³ Ooka, T.⁴

43
- 0028930270
- 16695s
- 3F: 234.0440; found: 234.0441; previously used in Mitsunobu reactions: Verheggen, I.; Van Aerschat, A.; Van Meervelt, L.; Rozenski, J.; Wiebe, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1995, 38, 826-835.
- (1977) Chem. Abs. , vol.86

44
- 0028930270
- note
- 3F: 234.0440; found: 234.0441; previously used in Mitsunobu reactions: Verheggen, I.; Van Aerschat, A.; Van Meervelt, L.; Rozenski, J.; Wiebe, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1995, 38, 826-835.

45
- 0028930270
- previously used in Mitsunobu reactions
- 3F: 234.0440; found: 234.0441; previously used in Mitsunobu reactions: Verheggen, I.; Van Aerschat, A.; Van Meervelt, L.; Rozenski, J.; Wiebe, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1995, 38, 826-835.
- (1995) J. Med. Chem. , vol.38 , pp. 826-835
- Verheggen, I.¹ Van Aerschat, A.² Van Meervelt, L.³ Rozenski, J.⁴ Wiebe, L.⁵ Snoeck, R.⁶ Andrei, G.⁷ Balzarini, J.⁸ De Clercq, E.⁹

46
- 0010384255
- note
- 2) using hexane/prop-2-OH mixtures as eluents were shown to give excellent results. We are indebted to Dr. K. Mohr and Mrs. R. Ziehn for their valuable assistance with these HPLC investigations.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.