SCOPUS 정보 검색 플랫폼

Volumn 10, Issue 46, 2012, Pages 9278-9286

Stereoselective synthesis and biological evaluation of d-fagomine, d-3-epi-fagomine and d-3,4-epi-fagomine analogs from d-glyceraldehyde acetonide as a common building block

(6) Díez, J Alberto a Gálvez, José A a Díaz De Villegas, María D a Badorrey, Ramón a Bartholomew, Barbara b Nash, Robert J b

a UNIVERSITY OF ZARAGOZA (Spain)

b Phytoquest Limited (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL EVALUATION; BUILDING BLOCKES; DIASTEREOSELECTIVE; GLYCOSIDASE INHIBITORS; REGIO-SELECTIVE; RING CLOSING METATHESIS; RING OPENING; STEREO-SELECTIVE; STEREOSELECTIVE DIHYDROXYLATION; STEREOSELECTIVE SYNTHESIS; THERAPEUTIC USE;

REGIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

STEREOSELECTIVITY;

CHAPERONE; DRUG DERIVATIVE; FAGOMINE; GLYCERALDEHYDE; GLYCERALDEHYDE ACETONIDE; IMINOSUGAR;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

GLYCERALDEHYDE; HYDROXYLATION; IMINO PYRANOSES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CHAPERONES; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84868658992 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c2ob26732b Document Type: Article

Times cited : (11)

References (43)

1
- 0003532642
- Wiley-VCH, Weinheim, Germany
- A. E. Stütz, Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond, Wiley-VCH, Weinheim, Germany, 1999
- (1999) Iminosugars As Glycosidase Inhibitors: Nojirimycin and beyond
- Stütz, A.E.¹

2
- 0034607947
- N. Asano R. J. Nash R. J. Molyneux G. W. J. Fleet Tetrahedron: Asymmetry 2000 11 1645
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 1645
- Asano, N.¹ Nash, R.J.² Molyneux, R.J.³ Fleet, G.W.J.⁴

3
- 0242287992
- For recent reviews on this subject see
- N. Asano Glycobiology 2003 13 93R
- (2003) Glycobiology , vol.13
- Asano, N.¹

4
- 84889478479
- John Wiley, Chichester
- P. Compain and O. R. Martin, Iminosugars: From Synthesis to Therapeutic Applications, John Wiley, Chichester, 2007
- (2007) Iminosugars: From Synthesis to Therapeutic Applications
- Compain, P.¹ Martin, O.R.²

5
- 80052454406
- R. J. Nash A. Kato C. Y. Yu G. W. J. Fleet Future Med. Chem. 2011 3 1513
- (2011) Future Med. Chem. , vol.3 , pp. 1513
- Nash, R.J.¹ Kato, A.² Yu, C.Y.³ Fleet, G.W.J.⁴

6
- 79951660094
- G. Horne F. X. Wilson Prog. Med. Chem. 2011 50 135
- (2011) Prog. Med. Chem. , vol.50 , pp. 135
- Horne, G.¹ Wilson, F.X.²

7
- 79952588456
- D. S. Alonzi T. D. Butters Chimia 2011 65 35
- (2011) Chimia , vol.65 , pp. 35
- Alonzi, D.S.¹ Butters, T.D.²

8
- 79851508769
- G. Horne F. X. Wilson J. Tinsley D. H. Williams R. Storer Drug Discovery Today 2011 16 107
- (2011) Drug Discovery Today , vol.16 , pp. 107
- Horne, G.¹ Wilson, F.X.² Tinsley, J.³ Williams, D.H.⁴ Storer, R.⁵

9
- 0016148809
- See
- M. Koyama S. Sakamura Agric. Biol. Chem. 1974 38 1111
- (1974) Agric. Biol. Chem. , vol.38 , pp. 1111
- Koyama, M.¹ Sakamura, S.²

10
- 84858707806
- references herein
- S. Amézqueta E. Galán E. Fuguet M. Carrascal J. Abián J. L. Torres Anal. Bioanal. Chem. 2012 402 1953
- (2012) Anal. Bioanal. Chem. , vol.402 , pp. 1953
- Amézqueta, S.¹ Galán, E.² Fuguet, E.³ Carrascal, M.⁴ Abián, J.⁵ Torres, J.L.⁶

11
- 0031896786
- H. Nojima I. Kimura F. J. Chen Y. Sugihara M. Haruno J. Nat. Prod. 1998 61 397
- (1998) J. Nat. Prod. , vol.61 , pp. 397
- Nojima, H.¹ Kimura, I.² Chen, F.J.³ Sugihara, Y.⁴ Haruno, M.⁵

12
- 0032425224
- S. Taniguchi N. Asano F. Tomino I. Miwa Horm. Metab. Res. 1998 30 679
- (1998) Horm. Metab. Res. , vol.30 , pp. 679
- Taniguchi, S.¹ Asano, N.² Tomino, F.³ Miwa, I.⁴

13
- 84858704307
- L. Gómez E. Molinar-Toribio M. A. Calvo-Torras C. Adelantado M. E. Juan J. M. Planas X. Cañas C. Lozano S. Pumarola P. Clapés J. L. Torres Br. J. Nutr. 2012 107 1739
- (2012) Br. J. Nutr. , vol.107 , pp. 1739
- Gómez, L.¹ Molinar-Toribio, E.² Calvo-Torras, M.A.³ Adelantado, C.⁴ Juan, M.E.⁵ Planas, J.M.⁶ Cañas, X.⁷ Lozano, C.⁸ Pumarola, S.⁹ Clapés, P.¹⁰ Torres, J.L.¹¹

14
- 0030900733
- Some recent syntheses of fagomine are
- A. Kato N. Asano H. Kizu K. Matsui J. Nat. Prod. 1997 60 312
- (1997) J. Nat. Prod. , vol.60 , pp. 312
- Kato, A.¹ Asano, N.² Kizu, H.³ Matsui, K.⁴

15
- 0034897853
- J. Désiré P. J. Dransfield P. M. Gore M. Shipman Synlett 2001 1329
- (2001) Synlett , pp. 1329
- Désiré, J.¹ Dransfield, P.J.² Gore, P.M.³ Shipman, M.⁴

16
- 33846128748
- J. A. Castillo J. Calveras J. Casas M. Mitjans M. P. Vinardell T. Parella T. Inoue G. A. Sprenger J. Joglar P. Clapés Org. Lett. 2006 8 6067
- (2006) Org. Lett. , vol.8 , pp. 6067
- Castillo, J.A.¹ Calveras, J.² Casas, J.³ Mitjans, M.⁴ Vinardell, M.P.⁵ Parella, T.⁶ Inoue, T.⁷ Sprenger, G.A.⁸ Joglar, J.⁹ Clapés, P.¹⁰

17
- 34247601597
- H. Yokoyama H. Ejiri M. Miyazawa S. Yamaguchi Y. Hirai Tetrahedron: Asymmetry 2007 18 852
- (2007) Tetrahedron: Asymmetry , vol.18 , pp. 852
- Yokoyama, H.¹ Ejiri, H.² Miyazawa, M.³ Yamaguchi, S.⁴ Hirai, Y.⁵

18
- 63849112560
- Erratum: Synlet, 2010, 239
- L. Bartalia D. Scarpia A. Guarnaa C. Prandib E. G. Occhiato Synlett 2009 913
- (2009) Synlett , pp. 913
- Bartalia, L.¹ Scarpia, D.² Guarnaa, A.³ Prandib, C.⁴ Occhiato, E.G.⁵

19
- 80053487298
- L. Babich L. J. C. van Hemert A. Bury A. F. Hartog P. Falcicchio J. van der Oost T. van Herk R. Wever F. P. J. T. Rutjes Green Chem. 2011 13 2895
- (2011) Green Chem. , vol.13 , pp. 2895
- Babich, L.¹ Van Hemert, L.J.C.² Bury, A.³ Hartog, A.F.⁴ Falcicchio, P.⁵ Van Der Oost, J.⁶ Van Herk, T.⁷ Wever, R.⁸ Rutjes, F.P.J.T.⁹

20
- 80054862042
- For synthesis of fagomine diastereoisomers see
- J. Y. Kim Y. Mua X. Jin S. H. Park V. T. Pham D. K. Song K. Y. Lee W. H. Ham Tetrahedron 2011 67 9426
- (2011) Tetrahedron , vol.67 , pp. 9426
- Kim, J.Y.¹ Mua, Y.² Jin, X.³ Park, S.H.⁴ Pham, V.T.⁵ Song, D.K.⁶ Lee, K.Y.⁷ Ham, W.H.⁸

21
- 0035902404
- Y. Banba C. Abe H. Nemoto A. Kato I. Adachi H. Takahata Tetrahedron: Asymmetry 2001 12 817
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 817
- Banba, Y.¹ Abe, C.² Nemoto, H.³ Kato, A.⁴ Adachi, I.⁵ Takahata, H.⁶

22
- 0242500286
- H. Takahata Y. Banba H. Ouchi H. Nemoto A. Kato I. Adachi J. Org. Chem. 2003 68 3603
- (2003) J. Org. Chem. , vol.68 , pp. 3603
- Takahata, H.¹ Banba, Y.² Ouchi, H.³ Nemoto, H.⁴ Kato, A.⁵ Adachi, I.⁶

23
- 34250683090
- E. Ciliberti R. Galvani F. Gramazio S. Haddas F. Leonelli P. Passacantilli G. Piancatelli Eur. J. Org. Chem. 2007 1463
- (2007) Eur. J. Org. Chem. , pp. 1463
- Ciliberti, E.¹ Galvani, R.² Gramazio, F.³ Haddas, S.⁴ Leonelli, F.⁵ Passacantilli, P.⁶ Piancatelli, G.⁷

24
- 58649086312
- N. Kumari B. G. Reddy Y. D. Vankar Eur. J. Org. Chem. 2009 160
- (2009) Eur. J. Org. Chem. , pp. 160
- Kumari, N.¹ Reddy, B.G.² Vankar, Y.D.³

25
- 78249278507
- L. Bartali A. Casini A. Guarna E. G. Occhiato D. Scarpi Eur. J. Org. Chem. 2010 5831
- (2010) Eur. J. Org. Chem. , pp. 5831
- Bartali, L.¹ Casini, A.² Guarna, A.³ Occhiato, E.G.⁴ Scarpi, D.⁵

26
- 79955664763
- R. W. Bates P. S. Ng Tetrahedron Lett. 2011 52 2969
- (2011) Tetrahedron Lett. , vol.52 , pp. 2969
- Bates, R.W.¹ Ng, P.S.²

27
- 80051797158
- For synthesis of other fagomine analogues see
- P. K. Kundu S. K. Ghosh Tetrahedron: Asymmetry 2011 22 1090
- (2011) Tetrahedron: Asymmetry , vol.22 , pp. 1090
- Kundu, P.K.¹ Ghosh, S.K.²

28
- 2242450647
- F. Degiorgis M. Lombardo C. Trombini Org. Prep. Proced. Int. 1997 29 485
- (1997) Org. Prep. Proced. Int. , vol.29 , pp. 485
- Degiorgis, F.¹ Lombardo, M.² Trombini, C.³

29
- 36749049726
- M. Sugiyama Z. Hong P. H. Liang S. M. Dean L. J. Whalen W. A. Greenberg C. H. Wong J. Am. Chem. Soc. 2007 124 14811
- (2007) J. Am. Chem. Soc. , vol.124 , pp. 14811
- Sugiyama, M.¹ Hong, Z.² Liang, P.H.³ Dean, S.M.⁴ Whalen, L.J.⁵ Greenberg, W.A.⁶ Wong, C.H.⁷

30
- 70349971053
- For recent reviews see
- R. Fu Y. Dua Z. Y. Li W. X. Xu P. Q. Huang Tetrahedron 2009 65 9765
- (2009) Tetrahedron , vol.65 , pp. 9765
- Fu, R.¹ Dua, Y.² Li, Z.Y.³ Xu, W.X.⁴ Huang, P.Q.⁵

31
- 84864710135
- ed. J. Cossy, S. Arseniyadis and C. Meyer, Wiley-VCH, Weinheim, Germany, 45-81
- S. [Bas] A. M. W. van den Broek, S. A. Meeuwissen, F. L. Delft and F. P. J. T. Rutjes, Natural Products Containing Medium-Sized Nitrogen Heterocycles Synthesized by Ring-Closing Alkene Metathesis in Metathesis in Natural Product Synthesis, ed., J. Cossy, S. Arseniyadis, and, C. Meyer, Wiley-VCH, Weinheim, Germany, 2010, pp. 45-81
- (2010) Natural Products Containing Medium-Sized Nitrogen Heterocycles Synthesized by Ring-Closing Alkene Metathesis in Metathesis in Natural Product Synthesis
- Van Den Broek, S.A.M.W.¹ Meeuwissen, S.A.² Delft, F.L.³ Rutjes, F.P.J.T.⁴

32
- 77957150234
- D. J. Wardrop S. L. Waidyarachchi Nat. Prod. Rep. 2010 27 1431
- (2010) Nat. Prod. Rep. , vol.27 , pp. 1431
- Wardrop, D.J.¹ Waidyarachchi, S.L.²

33
- 79958029774
- I. Dragutan V. Dragutan C. Mitan H. C. M. Vosloo L. Delaude A. Demonceau Beilstein J. Org. Chem. 2011 7 699
- (2011) Beilstein J. Org. Chem. , vol.7 , pp. 699
- Dragutan, I.¹ Dragutan, V.² Mitan, C.³ Vosloo, H.C.M.⁴ Delaude, L.⁵ Demonceau, A.⁶

34
- 84859185003
- I. Dragutan V. Dragutana A. Demonceau RSC Adv. 2012 2 719
- (2012) RSC Adv. , vol.2 , pp. 719
- Dragutan, I.¹ Dragutana, V.² Demonceau, A.³

35
- 12344296928
- 1995, 72 Diastereoselectivity of the addition was determined by GC using a Supelco-SPB®-5 capillary GC column
- C. R. Schmid J. D. Bryant Org. Synth. Coll. 1998 9 450
- (1998) Org. Synth. Coll. , vol.9 , pp. 450
- Schmid, C.R.¹ Bryant, J.D.²

36
- 34250686268
- R. Díez R. Badorrey M. D. Díaz-de-Villegas J. A. Gálvez Eur. J. Org. Chem. 2007 2114
- (2007) Eur. J. Org. Chem. , pp. 2114
- Díez, R.¹ Badorrey, R.² Díaz-De-Villegas, M.D.³ Gálvez, J.A.⁴

37
- 71549146867
- A. C. Allepuz R. Badorrey M. D. Díaz-de-Villegas J. A. Gálvez Eur. J. Org. Chem. 2009 6172
- (2009) Eur. J. Org. Chem. , pp. 6172
- Allepuz, A.C.¹ Badorrey, R.² Díaz-De-Villegas, M.D.³ Gálvez, J.A.⁴

38
- 81255195757
- Ha-Hb = 8.3 Hz For a helpful review discussing RCM reactions with amine containing compounds see
- J. A. Gálvez M. D. Díaz-de-Villegas R. Badorrey P. López-Ram-de-Víu Org. Biomol. Chem. 2011 9 8155
- (2011) Org. Biomol. Chem. , vol.9 , pp. 8155
- Gálvez, J.A.¹ Díaz-De-Villegas, M.D.² Badorrey, R.³ López-Ram-De-Víu, P.⁴

39
- 34548410348
- P. Compain Adv. Synth. Catal. 2007 349 1829
- (2007) Adv. Synth. Catal. , vol.349 , pp. 1829
- Compain, P.¹

40
- 33645897192
- 1H NMR spectroscopy using 1,3,5- trimethoxybenzene as an internal standard
- R. W. Hoffmann Chem. Rev. 1989 89 1841
- (1989) Chem. Rev. , vol.89 , pp. 1841
- Hoffmann, R.W.¹

41
- 49549130554
- d-Glucosidase from yeast (Saccharomyces cerevisiae), α-d- glucosidase from Bacillus stearothermophilus, α-d-glucosidase from rice (Oryza sativa), β-d-glucosidase from almond, α-d-galactosidase from green coffee bean (Coffea sp.), β-d-galactosidase from bovine liver, α-d-mannosidase from jack bean (Canavalia ensiformis), β-d-mannosidase from Cellullomonas fimi, β-d-glucuronidase from bovine liver, N-acetyl-β-d-glucosaminidase from bovine kidney, and N-acetyl-β-d-glucosaminidase from jack bean Residual solvent signals set according to
- V. VanRheenen R. C. Kelly D. Y. Cha Tetrahedron Lett. 1976 17 1973
- (1976) Tetrahedron Lett. , vol.17 , pp. 1973
- Vanrheenen, V.¹ Kelly, R.C.² Cha, D.Y.³

42
- 77951864540
- G. R. Fulmer A. J. M. Miller N. H. Sherden H. E. Gottlieb A. Nudelman B. M. Stolz J. E. Bercaw K. I. Goldberg Organometallics 2010 29 2176
- (2010) Organometallics , vol.29 , pp. 2176
- Fulmer, G.R.¹ Miller, A.J.M.² Sherden, N.H.³ Gottlieb, H.E.⁴ Nudelman, A.⁵ Stolz, B.M.⁶ Bercaw, J.E.⁷ Goldberg, K.I.⁸

43
- 0030864539
- R (anti) = 8.43 min
- A. A. Watson R. J. Nash M. R. Wormald D. J. Harvey S. Dealler E. Lees N. Asano H. Kizu A. Kato R. C. Griffiths A. J. Cairns G. W. J. Fleet Phytochemistry 1997 46 255
- (1997) Phytochemistry , vol.46 , pp. 255
- Watson, A.A.¹ Nash, R.J.² Wormald, M.R.³ Harvey, D.J.⁴ Dealler, S.⁵ Lees, E.⁶ Asano, N.⁷ Kizu, H.⁸ Kato, A.⁹ Griffiths, R.C.¹⁰ Cairns, A.J.¹¹ Fleet, G.W.J.¹²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.