메뉴 건너뛰기




Volumn 22, Issue 7-8, 2003, Pages 537-548

Synthesis of Acyclic C-Nucleoside Analogues Using (E)-1,2-Dideoxy-1- dimethylamino-4,5:6,7-di-O-isopropylidene-D-arabino-hept-1-en-3-ulose

Author keywords

C Nucleoside analogues; Heptenuloses; Push pull alkenes; Pyrazoles; Pyrimidines; Tetritols

Indexed keywords

1 ACETYL 5 (1,2:3,4 DI O ISOPROPYLIDENE DEXTRO ARABINOTETRITOL 1 YL) 1H PYRAZOLE; 1 DEOXY 3,4:5,6 DI O ISOPROPYLIDENE DEXTRO ARABINOHEX 2 ULOSE; 1,2 DIDEOXY 1 DIMETHYLAMINO 4,5:6,7 DI O ISOPROPYLIDENE DEXTRO ARABINOHEPT 1 EN 3 ULOSE; 2 AMINO 4 (1,2:3,4 DI O ISOPROPYLIDENE DEXTRO ARABINOTETRITOL 1 YL)PYRIMIDINE; 2 AMINO 4 (DEXTRO ARABINOTETRITOL 1 YL)PYRIMIDINE; 2 METHYL 4 (DEXTRO ARABINOTETRITOL 1 YL)PYRIMIDINE; 2 PHENYL 4 (DEXTRO ARABINOTETRITOL 1 YL)PYRIMIDINE; 3 (1,2:3,4 DI O ISOPROPYLIDENE DEXTRO ARABINOTETRITOL 1 YL) 1H PYRAZOLE; 3 (DEXTRO ARABINOTETRITOL 1 YL) 1H PYRAZOLE; 4 (1,2:3,4 DI O ISOPROPYLIDENE DEXTRO ARABINOTETRITOL 1 YL) 2 METHYLPYRIMIDINE; 4 (1,2:3,4 DI O ISOPROPYLIDENE DEXTRO ARABINOTETRITOL 1 YL) 2 PHENYLPYRIMIDINE; ACICLOVIR; AMIDINE; ANTIBIOTIC AGENT; ANTIVIRUS AGENT; CARBOHYDRATE DERIVATIVE; GUANIDINE DERIVATIVE; HYDRAZIDE DERIVATIVE; HYDROCHLORIC ACID; METHANE; N,N DIMETHYLFORMAMIDE; NUCLEOSIDE DERIVATIVE; PYRAZOLE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0347478170     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120026457     Document Type: Article
Times cited : (5)

References (30)
  • 2
    • 0347860656 scopus 로고
    • Baldwin, J.E., Magnus, P.D., Eds.; Pergamon: Oxford
    • Levy, D.E.; Tang, C. The Chemistry of C-Glycosides; Baldwin, J.E., Magnus, P.D., Eds.; Pergamon: Oxford, 1995; 7-22.
    • (1995) The Chemistry of C-Glycosides , pp. 7-22
    • Levy, D.E.1    Tang, C.2
  • 3
    • 33750865454 scopus 로고    scopus 로고
    • The chemistry of C-nucleosides and their analogs I. C-nucleosides of hetero monocyclic bases
    • Shaban, M.A.E.; Nasr, A.Z. The chemistry of C-nucleosides and their analogs I. C-nucleosides of hetero monocyclic bases. Adv. Heterocycl. Chem. 1997, 68, 223-432.
    • (1997) Adv. Heterocycl. Chem. , vol.68 , pp. 223-432
    • Shaban, M.A.E.1    Nasr, A.Z.2
  • 4
    • 35848959258 scopus 로고    scopus 로고
    • The chemistry of C-nucleosides and their analogs II. C-Nucleosides of condensed heterocyclic bases
    • Shaban, M.A.E. The chemistry of C-nucleosides and their analogs II. C-Nucleosides of condensed heterocyclic bases. Adv. Heterocycl. Chem. 1997, 70, 163-337.
    • (1997) Adv. Heterocycl. Chem. , vol.70 , pp. 163-337
    • Shaban, M.A.E.1
  • 5
    • 0023227592 scopus 로고
    • CV-1, a new antibiotic produced by a strain of Streptomyces sp. II. Structure determination
    • Yasuzawa, T.; Yoshida, M.; Ichimura, M.; Shirahata, K.; Sano, H. CV-1, a new antibiotic produced by a strain of Streptomyces sp. II. structure determination. J. Antibiot. 1987, 40, 727-731.
    • (1987) J. Antibiot. , vol.40 , pp. 727-731
    • Yasuzawa, T.1    Yoshida, M.2    Ichimura, M.3    Shirahata, K.4    Sano, H.5
  • 7
    • 0038270061 scopus 로고    scopus 로고
    • Antifungal metabolites from the marine sponge Pachastrissa sp.: New bengamide and bengazole derivatives
    • Fernández, R.; Dherbomez, M.; Letourneux, Y.; Nabil, M.; Verbist, J.F.; Biard, J.F. Antifungal metabolites from the marine sponge Pachastrissa sp.: new bengamide and bengazole derivatives. J. Nat. Prod. 1999, 62, 678-680.
    • (1999) J. Nat. Prod. , vol.62 , pp. 678-680
    • Fernández, R.1    Dherbomez, M.2    Letourneux, Y.3    Nabil, M.4    Verbist, J.F.5    Biard, J.F.6
  • 8
    • 0029080502 scopus 로고
    • Syntheses and absolute structures of the disaccharide and aglycone of acaricidal gualamycin
    • Tatsuta, K.; Kitagawa, M.; Horiuchi, T.; Tsuchiya, K.; Shimada, N. Syntheses and absolute structures of the disaccharide and aglycone of acaricidal gualamycin. J. Antibiot. 1995, 48, 741-744.
    • (1995) J. Antibiot. , vol.48 , pp. 741-744
    • Tatsuta, K.1    Kitagawa, M.2    Horiuchi, T.3    Tsuchiya, K.4    Shimada, N.5
  • 9
    • 0029085611 scopus 로고
    • Gualamycin, a novel acaricide produced by Streptomyces sp. NK11687.1. Taxonomy, production, isolation, and preliminary characterization
    • Tsuchiya, K.; Kobayashi, S.; Harada, T.; Kurokawa, T.; Nakagawa, T.; Shimada, N.; Kobayashi, K. Gualamycin, a novel acaricide produced by Streptomyces sp. NK11687.1. Taxonomy, production, isolation, and preliminary characterization. J. Antibiot. 1995, 48, 626-629.
    • (1995) J. Antibiot. , vol.48 , pp. 626-629
    • Tsuchiya, K.1    Kobayashi, S.2    Harada, T.3    Kurokawa, T.4    Nakagawa, T.5    Shimada, N.6    Kobayashi, K.7
  • 10
    • 0022532716 scopus 로고
    • Chemistry and antiviral activities of acyclonucleosides
    • Chu, C.K.; Cutler, S.J. Chemistry and antiviral activities of acyclonucleosides. J. Heterocycl. Chem. 1986, 23, 289-319.
    • (1986) J. Heterocycl. Chem. , vol.23 , pp. 289-319
    • Chu, C.K.1    Cutler, S.J.2
  • 11
    • 0002420102 scopus 로고
    • A new approach to C-branched monosaccharides by the stereoselective hydrodesulfurization of methyl 4,6-O-benzyli-dene-3-[bis(methylthio)methylene]- 3-deoxy-α-D-erythro-hexopyranosid-2-ulose
    • Peseke, K.; Thiele, G.; Michalik, M. A new approach to C-branched monosaccharides by the stereoselective hydrodesulfurization of methyl 4,6-O-benzyli-dene-3-[bis(methylthio)methylene]-3-deoxy-α-D-erythro- hexopyranosid-2-ulose. Liebigs Ann. Chem. 1995, 1633-1636.
    • (1995) Liebigs Ann. Chem. , pp. 1633-1636
    • Peseke, K.1    Thiele, G.2    Michalik, M.3
  • 13
    • 0347874168 scopus 로고    scopus 로고
    • An approach to C-branched and heterocyclic annelated pyranosides by reaction of α-D-erythro-hexopyranosid-2-ulose with orthoformic acid derivatives
    • Kuhla, B.; Peseke, K.; Thiele, G.; Michalik, M. An approach to C-branched and heterocyclic annelated pyranosides by reaction of α-D-erythro-hexopyranosid-2-ulose with orthoformic acid derivatives. J. Prakt. Chem. 2000, 342, 240-244.
    • (2000) J. Prakt. Chem. , vol.342 , pp. 240-244
    • Kuhla, B.1    Peseke, K.2    Thiele, G.3    Michalik, M.4
  • 14
    • 0034365633 scopus 로고    scopus 로고
    • Syntheses of pyrazole iso-C-nucleosides
    • Michalik, D.; Peseke, K. Syntheses of pyrazole iso-C-nucleosides. J. Carbohydr. Chem. 2000, 19, 1049-1057.
    • (2000) J. Carbohydr. Chem. , vol.19 , pp. 1049-1057
    • Michalik, D.1    Peseke, K.2
  • 15
    • 0035850191 scopus 로고    scopus 로고
    • Synthesis of derivatives of C-nucleoside analogues using 'push-pull' functionalized monosaccharides
    • Michalik, D.; Feist, H.; Peseke, K. Synthesis of derivatives of C-nucleoside analogues using 'push-pull' functionalized monosaccharides. Carbohydr. Res. 2001, 333, 197-201.
    • (2001) Carbohydr. Res. , vol.333 , pp. 197-201
    • Michalik, D.1    Feist, H.2    Peseke, K.3
  • 16
    • 0035648908 scopus 로고    scopus 로고
    • Synthesis of (2,3,4,6-tetra-O-acetyl-α-D-glycopyranosyl)thiophene derivatives as new C-nucleoside analogs
    • Garcia, I.; Feist, H.; Cao, R.; Michalik, M.; Peseke, K. Synthesis of (2,3,4,6-tetra-O-acetyl-α-D-glycopyranosyl)thiophene derivatives as new C-nucleoside analogs. J. Carbohydr. Chem. 2001, 20, 681-687.
    • (2001) J. Carbohydr. Chem. , vol.20 , pp. 681-687
    • Garcia, I.1    Feist, H.2    Cao, R.3    Michalik, M.4    Peseke, K.5
  • 18
    • 2842610640 scopus 로고    scopus 로고
    • Syntheses of acyclo-C-nucleosides by ring transformation of 2(3)-formylglycals
    • Rudloff, I.; Peseke, K.; Reinke, H. Syntheses of acyclo-C-nucleosides by ring transformation of 2(3)-formylglycals. J. Prakt. Chem. 1998, 340, 334-340.
    • (1998) J. Prakt. Chem. , vol.340 , pp. 334-340
    • Rudloff, I.1    Peseke, K.2    Reinke, H.3
  • 19
    • 0034840665 scopus 로고    scopus 로고
    • A facile synthesis of acyclo-C-nucleoside analogues from 2(3)-formylglycals
    • Rudloff, I.; Michalik, M.; Montera, A.; Peseke, K. A facile synthesis of acyclo-C-nucleoside analogues from 2(3)-formylglycals. Synthesis 2001, 1686-1692.
    • (2001) Synthesis , pp. 1686-1692
    • Rudloff, I.1    Michalik, M.2    Montera, A.3    Peseke, K.4
  • 20
  • 21
    • 0002311470 scopus 로고
    • Addition of diazomethane and sulfur ylides to the oxo-group in derivatives of ketoses and aldoses. Part 2. Reactions of 1-deoxy-3,4-O- isopropylidene-D-glycero-tetrulose and 1-deoxy-3,4:5,6-di-O-isopropylidene-L- arabino-hexulose
    • Anthonsen, T.; Hagen, S.; Luande, W. Addition of diazomethane and sulfur ylides to the oxo-group in derivatives of ketoses and aldoses. Part 2. Reactions of 1-deoxy-3,4-O-isopropylidene-D-glycero-tetrulose and 1-deoxy-3,4:5,6-di-O-isopropylidene-L-arabino-hexulose. Acta Chem. Scand. 1980, B 34, 41-45.
    • (1980) Acta Chem. Scand. , vol.B 34 , pp. 41-45
    • Anthonsen, T.1    Hagen, S.2    Luande, W.3
  • 22
    • 84872641084 scopus 로고
    • Acetone derivatives of hexahydric alcohols. I. Triacetone mannitol and its conversion into D-arabinose
    • Wiggins, L.F. Acetone derivatives of hexahydric alcohols. I. Triacetone mannitol and its conversion into D-arabinose. J. Chem. Soc. 1946, 13-14.
    • (1946) J. Chem. Soc. , pp. 13-14
    • Wiggins, L.F.1
  • 24
    • 84982335177 scopus 로고
    • Synthesis of L-gulomethylitol and D-rhamnitol by a new method
    • Gätzi, K.; Reichstein, T. Synthesis of L-gulomethylitol and D-rhamnitol by a new method. Helv. Chim. Acta 1938, 27, 914-925.
    • (1938) Helv. Chim. Acta , vol.27 , pp. 914-925
    • Gätzi, K.1    Reichstein, T.2
  • 25
    • 0000888922 scopus 로고
    • A new synthesis of aryl mono C-glycosyl derivatives of dialdehyde sugars
    • Krauß, G.A.; Shi, J. A new synthesis of aryl mono C-glycosyl derivatives of dialdehyde sugars. J. Org. Chem. 1990, 55, 4922-4925.
    • (1990) J. Org. Chem. , vol.55 , pp. 4922-4925
    • Krauß, G.A.1    Shi, J.2
  • 27
    • 0001115841 scopus 로고
    • The synthesis of mannich bases from ketones and esters via enaminones
    • Schuda, P.F.; Ebner, C.B.; Morgan, T.M. The synthesis of mannich bases from ketones and esters via enaminones. Tetrahedron Lett. 1986, 27, 2548-2666.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 2548-2666
    • Schuda, P.F.1    Ebner, C.B.2    Morgan, T.M.3
  • 28
    • 33751385862 scopus 로고
    • An extremely simple, convenient, and selective method for acetylating primary alcohols in the presence of secondary alcohols
    • Ishihara, K.; Kurihara, H.; Yamamoto, H. An extremely simple, convenient, and selective method for acetylating primary alcohols in the presence of secondary alcohols. J. Org. Chem. 1993, 55, 3791-3793.
    • (1993) J. Org. Chem. , vol.55 , pp. 3791-3793
    • Ishihara, K.1    Kurihara, H.2    Yamamoto, H.3
  • 29
    • 0000333645 scopus 로고
    • Synthesis of methyl 2-deoxy-4,5:6,7-di-O-isopropylidene-D-arabino-hept-3- ulosonate and its use in the preparation of D-arabino- tetrahydroxybutylpyrimidine derivatives
    • Valpuesta Fernandez, M.; Lopez Herrera, F.J.; Gomez Perez, C. Synthesis of methyl 2-deoxy-4,5:6,7-di-O-isopropylidene-D-arabino-hept-3-ulosonate and its use in the preparation of D-arabino-tetrahydroxybutylpyrimidine derivatives. Carbohydr. Res. 1983, 124, 333-337.
    • (1983) Carbohydr. Res. , vol.124 , pp. 333-337
    • Valpuesta Fernandez, M.1    Lopez Herrera, F.J.2    Gomez Perez, C.3
  • 30
    • 33845375225 scopus 로고
    • The total synthesis of 12-HETE (12-hydroxyeicosatetraenoic acid) and 12,20-diHETE
    • Leblanc, Y.; Fitzsimmons, B.J.; Adams, J.; Perez, F.; Rokach, J. The total synthesis of 12-HETE (12-hydroxyeicosatetraenoic acid) and 12,20-diHETE. J. Org. Chem. 1986, 789-793.
    • (1986) J. Org. Chem. , pp. 789-793
    • Leblanc, Y.1    Fitzsimmons, B.J.2    Adams, J.3    Perez, F.4    Rokach, J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.