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Angewandte Chemie - International Edition

Volumn 49, Issue 46, 2010, Pages 8724-8728

Fluorine-directed glycosylation

(2) Bucher, Christoph a Gilmour, Ryan a

a ETH ZURICH (Switzerland)

Author keywords

bioisosteres; conformational analysis; fluoroglycosides; organofluorine chemistry; oxonium ions

Indexed keywords

BIOISOSTERES; CONFORMATIONAL ANALYSIS; FLUOROGLYCOSIDES; ORGANOFLUORINE; OXONIUM ION;

FLUORINE; IONS;

CONFORMATIONS;

FLUORINE; ION;

ARTICLE; CHEMISTRY; GLYCOSYLATION; STATIC ELECTRICITY; STEREOISOMERISM;

FLUORINE; GLYCOSYLATION; IONS; STATIC ELECTRICITY; STEREOISOMERISM;

EID: 78149417694 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201004467 Document Type: Article

Times cited : (107)

References (72)

1
- 78149422476
- Nature Insight: Glycochemistry and Glycobiology 2007, 446, 9991051
- (2007) Nature Insight: Glycochemistry and Glycobiology , vol.446 , pp. 9991051

2
- 0035818475
- N. S. Sampson, M. Mrksich, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2001, 98, 12870 12871
- (2001) Proc. Natl. Acad. Sci. USA , vol.98 , pp. 12870-12871
- Sampson, N.S.¹ Mrksich, M.² Bertozzi, C.R.³

3
- 0035937499
- C. R. Bertozzi, L. L. Kiessling, Science 2001, 291, 2357 2364
- (2001) Science , vol.291 , pp. 2357-2364
- Bertozzi, C.R.¹ Kiessling, L.L.²

4
- 65949123149
- P. H. Seeberger, Nat. Chem. Biol. 2009, 5, 368 372.
- (2009) Nat. Chem. Biol. , vol.5 , pp. 368-372
- Seeberger, P.H.¹

5
- 0012630964
- K. C. Nicolaou, H. J. Mitchell, Angew. Chem. 2001, 113, 1624 1672
- (2001) Angew. Chem. , vol.113 , pp. 1624-1672
- Nicolaou, K.C.¹ Mitchell, H.J.²

6
- 0035805264
- Angew. Chem. Int. Ed. 2001, 40, 1576 1624
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1576-1624

7
- 84890989536
- (Ed.: A.V. Demchenko), Wiley-VCH, Weinheim
- Handbook of Chemical Glycosylation (Ed.:, A.V. Demchenko,), Wiley-VCH, Weinheim, 2008
- (2008) Handbook of Chemical Glycosylation

8
- 5244279498
- K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503 1531.
- (1993) Chem. Rev. , vol.93 , pp. 1503-1531
- Toshima, K.¹ Tatsuta, K.²

9
- 34748851889
- H. H. Jensen, C. M. Pedersen, M. Bols, Chem. Eur. J. 2007, 13, 7576 7582
- (2007) Chem. Eur. J. , vol.13 , pp. 7576-7582
- Jensen, H.H.¹ Pedersen, C.M.² Bols, M.³

10
- 75149138701
- L. K. Mydock, A. V. Demchenko, Org. Biomol. Chem. 2010, 8, 497 510
- (2010) Org. Biomol. Chem. , vol.8 , pp. 497-510
- Mydock, L.K.¹ Demchenko, A.V.²

11
- 77955700674
- D. Crich, Acc. Chem. Res. 2010, 43, 1144 1153.
- (2010) Acc. Chem. Res. , vol.43 , pp. 1144-1153
- Crich, D.¹

12
- 0037123262
- T. Nukada, A. Börces, D. M. Whitfield, Carbohydr. Res. 2002, 337, 765 774
- (2002) Carbohydr. Res. , vol.337 , pp. 765-774
- Nukada, T.¹ Börces, A.² Whitfield, D.M.³

13
- 0004117284
- Verlag Chemie, Weinheim
- P. Hartwig, Oxonium Ions in Organic Chemistry, Verlag Chemie, Weinheim, 1971.
- (1971) Oxonium Ions in Organic Chemistry
- Hartwig, P.¹

14
- 0000562875
- Special Problems in Glycosidation Reactions: 2-Deoxy Sugars: in (Eds.: B. Ernst, G.W. Hart, P. Sinaý), Wiley-VCH, Weinheim, pp. 405
- Special Problems in Glycosidation Reactions: 2-Deoxy Sugars:, A. Veyrières, in Carbohydrates in Chemistry and Biology, Vol.I (Eds.:, B. Ernst, G.W. Hart, P. Sinaý,), Wiley-VCH, Weinheim, 2000, pp. 367 405
- (2000) Carbohydrates in Chemistry and Biology, Vol.I , pp. 367
- Veyrières, A.¹

15
- 0034639452
- J. Antoinette, C. Romero, S. A. Tabacco, K. A. Woerpel, J. Am. Chem. Soc. 2000, 122, 168 169
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 168-169
- Antoinette, J.¹ Romero, C.² Tabacco, S.A.³ Woerpel, K.A.⁴

16
- 0346850020
- L. Ayala, C. G. Lucero, J. Antionette, C. Romero, S. A. Tabacco, K. A. Woerpel, J. Am. Chem. Soc. 2003, 125, 15521 15528
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 15521-15528
- Ayala, L.¹ Lucero, C.G.² Antionette, J.³ Romero, C.⁴ Tabacco, S.A.⁵ Woerpel, K.A.⁶

17
- 23744510729
- C. H. Larsen, B. H. Ridgeway, J. T. Shaw, D. M. Smith, K. A. Woerpel, J. Am. Chem. Soc. 2005, 127, 10879 10884
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 10879-10884
- Larsen, C.H.¹ Ridgeway, B.H.² Shaw, J.T.³ Smith, D.M.⁴ Woerpel, K.A.⁵

18
- 33750024980
- G. Baghdasarian, K. A. Woerpel, J. Org. Chem. 2006, 71, 6851 6858
- (2006) J. Org. Chem. , vol.71 , pp. 6851-6858
- Baghdasarian, G.¹ Woerpel, K.A.²

19
- 60849138810
- M. T. Yang, K. A. Woerpel, J. Org. Chem. 2009, 74, 545 553
- (2009) J. Org. Chem. , vol.74 , pp. 545-553
- Yang, M.T.¹ Woerpel, K.A.²

20
- 70350714361
- J. R. Krumper, W. A. Salamant, K. A. Woerpel, J. Org. Chem. 2009, 74, 8039 8050
- (2009) J. Org. Chem. , vol.74 , pp. 8039-8050
- Krumper, J.R.¹ Salamant, W.A.² Woerpel, K.A.³

21
- 0033541144
- R. Roush, R. A. Hartz, D. J. Gustin, J. Am. Chem. Soc. 1999, 121, 1990 1991
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 1990-1991
- Roush, R.¹ Hartz, R.A.² Gustin, D.J.³

22
- 0030843605
- W. R. Roush, D. P. Sebesta, C. E. Bennett, Tetrahedron 1997, 53, 8837 8852
- (1997) Tetrahedron , vol.53 , pp. 8837-8852
- Roush, W.R.¹ Sebesta, D.P.² Bennett, C.E.³

23
- 0029791485
- W. R. Roush, K. Briner, B. S. Kesler, M. Murphy, D. J. Gustin, J. Org. Chem. 1996, 61, 6098 6099
- (1996) J. Org. Chem. , vol.61 , pp. 6098-6099
- Roush, W.R.¹ Briner, K.² Kesler, B.S.³ Murphy, M.⁴ Gustin, D.J.⁵

24
- 0033553134
- W. R. Roush, C. E. Bennett, J. Am. Chem. Soc. 1999, 121, 3541 3542
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 3541-3542
- Roush, W.R.¹ Bennett, C.E.²

25
- 0037069724
- W. R. Roush, P. Chong, Org. Lett. 2002, 4, 4523 4526
- (2002) Org. Lett. , vol.4 , pp. 4523-4526
- Roush, W.R.¹ Chong, P.²

26
- 0033598252
- W. R. Roush, B. W. Gung, C. E. Bennett, Org. Lett. 1999, 1, 891 893
- (1999) Org. Lett. , vol.1 , pp. 891-893
- Roush, W.R.¹ Gung, B.W.² Bennett, C.E.³

27
- 0038476047
- N. Blanchard, W. R. Roush, Org. Lett. 2003, 5, 81 84.
- (2003) Org. Lett. , vol.5 , pp. 81-84
- Blanchard, N.¹ Roush, W.R.²

28
- 84987590199
- For selected examples of stereoelectronic and electrostatic effects see:, 1817
- For selected examples of stereoelectronic and electrostatic effects see:, J. J. Irwin, T.-K. Ha, J. D. Dunitz, Helv. Chim. Acta 1990, 73, 1805 1817
- (1990) Helv. Chim. Acta , vol.73 , pp. 1805
- Irwin, J.J.¹ Ha, T.-K.² Dunitz, J.D.³

29
- 0034175168
- D. OHagan, C. Bilton, J. A. K. Howard, L. Knight, D. J. Tozer, J. Chem. Soc. Perkin Trans. 2 2000, 605 607
- (2000) J. Chem. Soc. Perkin Trans. 2 , pp. 605-607
- Ohagan, D.¹ Bilton, C.² Howard, J.A.K.³ Knight, L.⁴ Tozer, D.J.⁵

30
- 0037207628
- C. R. S. Briggs, D. OHagan, J. A. K. Howard, D. S. Yufit, J. Fluorine Chem. 2003, 119, 9 13
- (2003) J. Fluorine Chem. , vol.119 , pp. 9-13
- Briggs, C.R.S.¹ Ohagan, D.² Howard, J.A.K.³ Yufit, D.S.⁴

31
- 1642345348
- C. R. S. Briggs, M. J. Allen, D. OHagan, D. J. Tozer, A. M. Z. Slawin, A. E. Goeta, J. A. K. Howard, Org. Biomol. Chem. 2004, 2, 732 740
- (2004) Org. Biomol. Chem. , vol.2 , pp. 732-740
- Briggs, C.R.S.¹ Allen, M.J.² Ohagan, D.³ Tozer, D.J.⁴ Slawin, A.M.Z.⁵ Goeta, A.E.⁶ Howard, J.A.K.⁷

32
- 67749084264
- C. Sparr, W. B. Schweizer, H. M. Senn, R. Gilmour, Angew. Chem. 2009, 121, 3111 3114
- (2009) Angew. Chem. , vol.121 , pp. 3111-3114
- Sparr, C.¹ Schweizer, W.B.² Senn, H.M.³ Gilmour, R.⁴

33
- 70349783652
- Angew. Chem. Int. Ed. 2009, 48, 3065 3068
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 3065-3068

34
- 67949094197
- C. Bucher, C. Sparr, W. B. Schweizer, R. Gilmour, Chem. Eur. J. 2009, 15, 7637 7647.
- (2009) Chem. Eur. J. , vol.15 , pp. 7637-7647
- Bucher, C.¹ Sparr, C.² Schweizer, W.B.³ Gilmour, R.⁴

35
- 0001267759
- D. C. Lankin, N. S. Chandrakumar, S. N. Rao, D. P. Spangler, J. P. Snyder, J. Am. Chem. Soc. 1993, 115, 3356 3357
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 3356-3357
- Lankin, D.C.¹ Chandrakumar, N.S.² Rao, S.N.³ Spangler, D.P.⁴ Snyder, J.P.⁵

36
- 0034716326
- J. P. Snyder, N. S. Chandrakumar, H. Sato, D. C. Lankin, J. Am. Chem. Soc. 2000, 122, 544 545
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 544-545
- Snyder, J.P.¹ Chandrakumar, N.S.² Sato, H.³ Lankin, D.C.⁴

37
- 0037126202
- D. C. Lankin, G. L. Grunewald, F. A. Romero, I. Y. Oren, J. P. Snyder, Org. Lett. 2002, 4, 3557 3560
- (2002) Org. Lett. , vol.4 , pp. 3557-3560
- Lankin, D.C.¹ Grunewald, G.L.² Romero, F.A.³ Oren, I.Y.⁴ Snyder, J.P.⁵

38
- 84962377223
- A. Sun, D. C. Lankin, K. Hardcastle, J. P. Snyder, Chem. Eur. J. 2005, 11, 1579 1591.
- (2005) Chem. Eur. J. , vol.11 , pp. 1579-1591
- Sun, A.¹ Lankin, D.C.² Hardcastle, K.³ Snyder, J.P.⁴

39
- 33746410059
- N. E. Gooseman, D. OHagan, A. M. Z. Slawin, A. M. Teatle, D. J. Tozer, R. J. Young, Chem. Commun. 2006, 3190 3192
- (2006) Chem. Commun. , pp. 3190-3192
- Gooseman, N.E.¹ Ohagan, D.² Slawin, A.M.Z.³ Teatle, A.M.⁴ Tozer, D.J.⁵ Young, R.J.⁶

40
- 54349104931
- N. E. Gooseman, D. OHagan, M. J. G. Peach, A. M. Z. Slawin, D. J. Tozer, R. J. Young, Angew. Chem. 2007, 119, 6008 6012
- (2007) Angew. Chem. , vol.119 , pp. 6008-6012
- Gooseman, N.E.¹ Ohagan, D.² Peach, M.J.G.³ Slawin, A.M.Z.⁴ Tozer, D.J.⁵ Young, R.J.⁶

41
- 34547781803
- Angew. Chem. Int. Ed. 2007, 46, 5904 5908.
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5904-5908

42
- 0000023645
- For a report of through-space electrostatic stabilization of oxonium ions by axially oriented electronegative substituent see:, 7604
- For a report of through-space electrostatic stabilization of oxonium ions by axially oriented electronegative substituent see:, M. Miljković, D. Yeagley, P. Deslongchamps, Y. L. Dory, J. Org. Chem. 1997, 62, 7597 7604.
- (1997) J. Org. Chem. , vol.62 , pp. 7597
- Miljković, M.¹ Yeagley, D.² Deslongchamps, P.³ Dory, Y.L.⁴

43
- 0034693085
- C. H. Marzabadi, R. W. Franck, Tetrahedron 2000, 56, 8385 8417
- (2000) Tetrahedron , vol.56 , pp. 8385-8417
- Marzabadi, C.H.¹ Franck, R.W.²

44
- 70349191385
- D. Hou, T. L. Lowary, Carbohydr. Res. 2009, 344, 1911 1940.
- (2009) Carbohydr. Res. , vol.344 , pp. 1911-1940
- Hou, D.¹ Lowary, T.L.²

45
- 4544278491
- J. D. Dunitz, ChemBioChem 2004, 5, 614 621
- (2004) ChemBioChem , vol.5 , pp. 614-621
- Dunitz, J.D.¹

46
- 38149016915
- D. OHagan, Chem. Soc. Rev. 2008, 37, 308 319
- (2008) Chem. Soc. Rev. , vol.37 , pp. 308-319
- Ohagan, D.¹

47
- 78149460626
- DOI:; see the special edition Fluorine in the Life Sciences
- L. Hunter, Beilstein J. Org. Chem. 2010, DOI:; see the special edition Fluorine in the Life Sciences
- (2010) Beilstein J. Org. Chem.
- Hunter, L.¹

48
- 78149418362
- ChemBioChem 2004, 5, 557726.
- (2004) ChemBioChem , vol.5 , pp. 557726

49
- 0022996027
- For selected examples see:, I. P. Street, C. R. Armstrong, S. G. Withers, Biochemistry 1986, 25, 6021 6027
- (1986) Biochemistry , vol.25 , pp. 6021-6027
- Street, I.P.¹ Armstrong, C.R.² Withers, S.G.³

50
- 0032860126
- M. Albert, B. J. Paul, K. Dax, Synlett 1999, 1483 1485
- (1999) Synlett , pp. 1483-1485
- Albert, M.¹ Paul, B.J.² Dax, K.³

51
- 0034926661
- B. Smart, J. Fluorine Chem. 2001, 109, 3 11
- (2001) J. Fluorine Chem. , vol.109 , pp. 3-11
- Smart, B.¹

52
- 27644511254
- N. Khan, N. Oriuchi, T. Higuchi, K. Endo, Cancer Res. 2005, 12, 254 260
- (2005) Cancer Res. , vol.12 , pp. 254-260
- Khan, N.¹ Oriuchi, N.² Higuchi, T.³ Endo, K.⁴

53
- 49849087072
- L. Cai, S. Lu, V. W. Pike, Eur. J. Org. Chem. 2008, 2853 2873
- (2008) Eur. J. Org. Chem. , pp. 2853-2873
- Cai, L.¹ Lu, S.² Pike, V.W.³

54
- 67650572144
- B. R. Rempel, S. G. Withers, Aust. J. Chem. 2009, 62, 590 599
- (2009) Aust. J. Chem. , vol.62 , pp. 590-599
- Rempel, B.R.¹ Withers, S.G.²

55
- 70350553833
- S. A. Allman, H. H. Jensen, B. Vijayakrishnan, J. A. Garnet, E. Leon, Y. Liu, D. C. Anthony, N. R. Sibson, T. Feizi, S. Matthews, B. G. Davis, ChemBioChem 2009, 10, 2522 2529
- (2009) ChemBioChem , vol.10 , pp. 2522-2529
- Allman, S.A.¹ Jensen, H.H.² Vijayakrishnan, B.³ Garnet, J.A.⁴ Leon, E.⁵ Liu, Y.⁶ Anthony, D.C.⁷ Sibson, N.R.⁸ Feizi, T.⁹ Matthews, S.¹⁰ Davis, B.G.¹¹

56
- 70349208720
- P. Stallforth, B. Lepenies, A. Adibekian, P. H. Seeberger, J. Med. Chem. 2009, 52, 5561 5577
- (2009) J. Med. Chem. , vol.52 , pp. 5561-5577
- Stallforth, P.¹ Lepenies, B.² Adibekian, A.³ Seeberger, P.H.⁴

57
- 77954783960
- S. Bresciani, T. Lebl, A. M. Z. Slawin, D. OHagan, Chem. Commun. 2010, 46, 5434 5436
- (2010) Chem. Commun. , vol.46 , pp. 5434-5436
- Bresciani, S.¹ Lebl, T.² Slawin, A.M.Z.³ Ohagan, D.⁴

58
- 78149426122
- DOI:. Also see the special edition Fluoro Sugars
- O. Boutureira, F. DHooge, M. Fernández-González, G.J.L. Bernardes, M. Sánchez-Navarro, J.R. Koeppe, B.G. Davis, Chem. Commun. 2010, DOI:. Also see the special edition Fluoro Sugars
- (2010) Chem. Commun.
- O. Boutureira¹

59
- 78149455096
- Carbohydr. Res. 2000, 327, 1218.
- (2000) Carbohydr. Res. , vol.327 , pp. 1218

60
- 0028186224
- R. R. Schmidt, W. Kinzy, Adv. Carbohydr. Chem. Biochem. 1994, 50, 21 123
- (1994) Adv. Carbohydr. Chem. Biochem. , vol.50 , pp. 21-123
- Schmidt, R.R.¹ Kinzy, W.²

61
- 66749158101
- X. Zhu, R. R. Schmidt, Angew. Chem. 2009, 121, 1932 1967
- (2009) Angew. Chem. , vol.121 , pp. 1932-1967
- Zhu, X.¹ Schmidt, R.R.²

62
- 61849111654
- Angew. Chem. Int. Ed. 2009, 48, 1900 1934.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1900-1934

63
- 33847643205
- For a study of 4,6-O-benzylidene-directed mannopyranosylation and glucopyranosylation using 2-deoxy-2-fluoro donors see, 1690
- For a study of 4,6-O-benzylidene-directed mannopyranosylation and glucopyranosylation using 2-deoxy-2-fluoro donors see, D. Crich, L. Li, J. Org. Chem. 2007, 72, 1681 1690.
- (2007) J. Org. Chem. , vol.72 , pp. 1681
- Crich, D.¹ Li, L.²

64
- 21344498990
- N. M. Spijker, J.-W. Slief, C. A. A. VanBoeckel, Carbohydr. Res. 1993, 12, 1017 1041.
- (1993) Carbohydr. Res. , vol.12 , pp. 1017-1041
- Spijker, N.M.¹ Slief, J.-W.² Vanboeckel, C.A.A.³

65
- 85022498621
- B. Fraser-Reid, U. E. Udodong, Z. Wu, H. Ottosson, J. R. Merritt, C. S. Rao, C. Roberts, R. Madsen, Synlett 1992, 927 942.
- (1992) Synlett , pp. 927-942
- Fraser-Reid, B.¹ Udodong, U.E.² Wu, Z.³ Ottosson, H.⁴ Merritt, J.R.⁵ Rao, C.S.⁶ Roberts, C.⁷ Madsen, R.⁸

66
- 33645319496
- D. M. Smith, K. A. Woerpel, Org. Biomol. Chem. 2006, 4, 1195 1201.
- (2006) Org. Biomol. Chem. , vol.4 , pp. 1195-1201
- Smith, D.M.¹ Woerpel, K.A.²

67
- 0003701938
- R. J. Woods, C. W. Andrews, J. P. Bowen, J. Am. Chem. Soc. 1992, 114, 850 858
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 850-858
- Woods, R.J.¹ Andrews, C.W.² Bowen, J.P.³

68
- 0000607797
- R. J. Woods, C. W. Andrews, J. P. Bowen, J. Am. Chem. Soc. 1992, 114, 859 864.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 859-864
- Woods, R.J.¹ Andrews, C.W.² Bowen, J.P.³

69
- 78149442364
- See the Supporting Information for a discussion
- See the Supporting Information for a discussion.

70
- 0003104047
- and references therein. For a theoretical study see
- N. T. Ahn, O. Eisenstein, Nouv. J. Chim. 1977, 1, 61 70, and references therein. For a theoretical study see
- (1977) Nouv. J. Chim. , vol.1 , pp. 61-70
- Ahn, N.T.¹ Eisenstein, O.²

71
- 37049084955
- S. S. Wong, M. N. Paddon-Row, J. Chem. Soc. Chem. Commun. 1990, 456 458
- (1990) J. Chem. Soc. Chem. Commun. , pp. 456-458
- Wong, S.S.¹ Paddon-Row, M.N.²

72
- 37049069454
- S. S. Wong, M. N. Paddown-Row, J. Chem. Soc. Chem. Commun. 1991, 327 330.
- (1991) J. Chem. Soc. Chem. Commun. , pp. 327-330
- Wong, S.S.¹ Paddown-Row, M.N.²

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