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Carbohydrate Research

Volumn 340, Issue 2, 2005, Pages 235-244

Synthesis of C-5-thioglycopyranosides and their sulfonium derivatives from 1-C-(2′-oxoalkyl)-5-S-acetylglycofuranosides

(3) Yi, Tian a Wu, Shih Hsiung b Zou, Wei a

a NATIONAL RESEARCH COUNCIL CANADA (Canada)

b INSTITUTE OF BIOLOGICAL CHEMISTRY (Taiwan)

Author keywords

C Glycoside; Inhibitor; NMR spectroscopy; Sulfonium; Synthesis; Thiosugar

Indexed keywords

CONJUGATED ALDEHYDES; CYCLOADDITION; STEREOSELECTIVITY;

ALDEHYDES; ESTERS; KETONES; SALTS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; XYLOSE;

CARBOHYDRATES;

ALDEHYDE; ARABINOSE; BASE; ESTER; FURAN DERIVATIVE; GLYCOPYRANOSIDE; KETONE; METHYL IODIDE; RIBOSE; SODIUM CHLORIDE; SULFATE; SULFONIUM DERIVATIVE; THIOL GROUP; XYLOSE;

ARTICLE; CONJUGATION; CYCLOADDITION; ELIMINATION REACTION; ISOMER; MICHAEL ADDITION; MOLECULE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

FURANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PYRANS; SULFONIUM COMPOUNDS; THIOGLYCOSIDES;

EID: 12144255580 PISSN: 00086215 EISSN: None Source Type: Journal
DOI: 10.1016/j.carres.2004.11.014 Document Type: Article

Times cited : (13)

References (55)

1
- 0035700506
- J.G. Fernandez-Bolanos, N.A. Al-Masoudi, and I. Maya Adv. Carbohydr. Chem. Biochem. 57 2001 21 98
- (2001) Adv. Carbohydr. Chem. Biochem. , vol.57 , pp. 21-98
- Fernandez-Bolanos, J.G.¹ Al-Masoudi, N.A.² Maya, I.³

2
- 0001367771
- B. Ganem Acc. Chem. Res. 29 1996 340 347
- (1996) Acc. Chem. Res. , vol.29 , pp. 340-347
- Ganem, B.¹

3
- 4243206142
- R. Garg, S.P. Gupta, H. Gao, M.S. Babu, A.K. Debnath, and C. Hansch Chem. Rev. 99 1999 3535 3601
- (1999) Chem. Rev. , vol.99 , pp. 3535-3601
- Garg, R.¹ Gupta, S.P.² Gao, H.³ Babu, M.S.⁴ Debnath, A.K.⁵ Hansch, C.⁶

4
- 0034006999
- L.J. Scott, and C.M. Spencer Drugs 59 2000 521 549
- (2000) Drugs , vol.59 , pp. 521-549
- Scott, L.J.¹ Spencer, C.M.²

5
- 0000258096
- J. Alper Science 291 2001 2338 2343
- (2001) Science , vol.291 , pp. 2338-2343
- Alper, J.¹

6
- 0032981076
- Z.J. Witczak Curr. Med. Chem. 6 1999 165 178
- (1999) Curr. Med. Chem. , vol.6 , pp. 165-178
- Witczak, Z.J.¹

7
- 0842320086
- I. Robina, P. Vogel, and Z.J. Witczak Curr. Org. Chem. 5 2001 1137 1214
- (2001) Curr. Org. Chem. , vol.5 , pp. 1137-1214
- Robina, I.¹ Vogel, P.² Witczak, Z.J.³

8
- 0036255696
- I. Robina, and P. Vogel Curr. Org. Chem. 6 2002 471 491
- (2002) Curr. Org. Chem. , vol.6 , pp. 471-491
- Robina, I.¹ Vogel, P.²

9
- 0030992604
- Z.J. Witczak, R. Chhabra, H. Chen, and X.-Q. Xie Carbohydr. Res. 301 1997 167 175
- (1997) Carbohydr. Res. , vol.301 , pp. 167-175
- Witczak, Z.J.¹ Chhabra, R.² Chen, H.³ Xie, X.-Q.⁴

10
- 0030778517
- Y.L. Merrer, M. Fuzier, I. Dosbaa, M.-J. Foglietti, and J.-C. Depezay Tetrahedron 53 1997 16731 16746
- (1997) Tetrahedron , vol.53 , pp. 16731-16746
- Merrer, Y.L.¹ Fuzier, M.² Dosbaa, I.³ Foglietti, M.-J.⁴ Depezay, J.-C.⁵

11
- 0003532642
- Wiley-VCH New York
- A.E. Stutz Iminosugars as Glycosidase Inhibitors Nojirimycin and Beyond 1999 Wiley-VCH New York
- (1999) Iminosugars as Glycosidase Inhibitors Nojirimycin and Beyond
- Stutz, A.E.¹

12
- 0036462605
- V.H. Lillelund, H.H. Jensen, X. Liang, and M. Bols Chem. Rev. 102 2002 515 553
- (2002) Chem. Rev. , vol.102 , pp. 515-553
- Lillelund, V.H.¹ Jensen, H.H.² Liang, X.³ Bols, M.⁴

13
- 0030670829
- M. Yoshikawa, T. Murakami, H. Shimada, H. Matsuda, J. Yamahara, G. Tanabe, and O. Muraoka Tetrahedron Lett. 38 1997 8367 8370
- (1997) Tetrahedron Lett. , vol.38 , pp. 8367-8370
- Yoshikawa, M.¹ Murakami, T.² Shimada, H.³ Matsuda, H.⁴ Yamahara, J.⁵ Tanabe, G.⁶ Muraoka, O.⁷

14
- 0031722553
- M. Yoshikawa, T. Murakami, K. Yashiro, and H. Matsuda Chem. Pharm. Bull. 46 1998 1339 1340
- (1998) Chem. Pharm. Bull. , vol.46 , pp. 1339-1340
- Yoshikawa, M.¹ Murakami, T.² Yashiro, K.³ Matsuda, H.⁴

15
- 0003914371
- National Science Council of Sri Lanka Colombo
- D.M.A. Jayaweera Medicinal Plants used in Ceylon. Part 1 1981 National Science Council of Sri Lanka Colombo p 77
- (1981) Medicinal Plants Used in Ceylon. Part 1
- Jayaweera, D.M.A.¹

16
- 0025151378
- S. Serasinghe, P. Seresinghe, H. Yamazaki, K. Nishiguchi, F. Hombhanje, S. Nakanishi, K. Sawa, M. Hattori, and T. Namba Phytother. Res. 4 1990 205 206
- (1990) Phytother. Res. , vol.4 , pp. 205-206
- Serasinghe, S.¹ Seresinghe, P.² Yamazaki, H.³ Nishiguchi, K.⁴ Hombhanje, F.⁵ Nakanishi, S.⁶ Sawa, K.⁷ Hattori, M.⁸ Namba, T.⁹

17
- 0037125513
- B.D. Johnston, A. Ghavami, M.T. Jensen, L. Svansson, and B.M. Pinto J. Am. Chem. Soc. 124 2002 8245 8250
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 8245-8250
- Johnston, B.D.¹ Ghavami, A.² Jensen, M.T.³ Svansson, L.⁴ Pinto, B.M.⁵

18
- 0038103855
- A. Ghavami, K.S. Sadalapure, B.D. Johnston, M. Lobera, B.B. Snider, and B.M. Pinto Synlett 2003 1259 1262
- (2003) Synlett , pp. 1259-1262
- Ghavami, A.¹ Sadalapure, K.S.² Johnston, B.D.³ Lobera, M.⁴ Snider, B.B.⁵ Pinto, B.M.⁶

19
- 0348047409
- A. Ghavami, J.J.-w. Chen, and B.M. Pinto Carbohydr. Res. 339 2004 401 407
- (2004) Carbohydr. Res. , vol.339 , pp. 401-407
- Ghavami, A.¹ Chen, J.J.-W.² Pinto, B.M.³

20
- 0035815146
- A. Ghavami, B.D. Johnston, and B.M. Pinto J. Org. Chem. 66 2001 2312 2317
- (2001) J. Org. Chem. , vol.66 , pp. 2312-2317
- Ghavami, A.¹ Johnston, B.D.² Pinto, B.M.³

21
- 0037453695
- V. Cere, S. Pollicino, and A. Ricci J. Org. Chem. 68 2003 3311 3314
- (2003) J. Org. Chem. , vol.68 , pp. 3311-3314
- Cere, V.¹ Pollicino, S.² Ricci, A.³

22
- 0029038739
- F. Bellamy, V. Barberousse, N. Martin, P. Passon, J. Millet, S. Samreth, C. Sepulchre, J. Theveniaux, and D. Horton Eur. J. Med. Chem. 30 1995 101 115
- (1995) Eur. J. Med. Chem. , vol.30 , pp. 101-115
- Bellamy, F.¹ Barberousse, V.² Martin, N.³ Passon, P.⁴ Millet, J.⁵ Samreth, S.⁶ Sepulchre, C.⁷ Theveniaux, J.⁸ Horton, D.⁹

23
- 0038697625
- L. Mignon, C. Goichot, P. Ratel, G. Cagnin, M. Baudry, J.-P. Praly, B. Boubia, and V. Barberousse Carbohydr. Res. 338 2003 1271 1282
- (2003) Carbohydr. Res. , vol.338 , pp. 1271-1282
- Mignon, L.¹ Goichot, C.² Ratel, P.³ Cagnin, G.⁴ Baudry, M.⁵ Praly, J.-P.⁶ Boubia, B.⁷ Barberousse, V.⁸

24
- 0032508934
- R. Ravishankar, A. Surolia, M. Vijayan, S. Lim, and Y. Kishi J. Am. Chem. Soc. 120 1998 11297 11303
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 11297-11303
- Ravishankar, R.¹ Surolia, A.² Vijayan, M.³ Lim, S.⁴ Kishi, Y.⁵

25
- 0029087780
- A. Wei, K.M. Boy, and Y. Kishi J. Am. Chem. Soc. 117 1995 9432 9436
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 9432-9436
- Wei, A.¹ Boy, K.M.² Kishi, Y.³

26
- 0033799298
- Different conformations between C- and O-glycosides, see: J. Jimenez-Barbero, J. Espinosa, J. Asensio, F. Canada, and A. Poveda Adv. Carbohydr. Chem. Biochem. 56 2000 235 284
- (2000) Adv. Carbohydr. Chem. Biochem. , vol.56 , pp. 235-284
- Jimenez-Barbero, J.¹ Espinosa, J.² Asensio, J.³ Canada, F.⁴ Poveda, A.⁵

27
- 0028360180
- K.A. Watson, E.P. Mitchell, L.N. Johnson, J.C. Son, C.J.F. Bichard, M.G. Orchard, G.W.J. Fleet, N.G. Oikonomakos, D.D. Leonidas, M. Kontou, and Papageorgioui Biochemistry 33 1994 5745 5758
- (1994) Biochemistry , vol.33 , pp. 5745-5758
- Watson, K.A.¹ Mitchell, E.P.² Johnson, L.N.³ Son, J.C.⁴ Bichard, C.J.F.⁵ Orchard, M.G.⁶ Fleet, G.W.J.⁷ Oikonomakos, N.G.⁸ Leonidas, D.D.⁹ Kontou, M.¹⁰ Papageorgioui¹¹

28
- 0026040398
- R.R. Schmidt, and H. Dietrich Angew. Chem., Int. Ed. Engl. 30 1991 1328 1329
- (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 1328-1329
- Schmidt, R.R.¹ Dietrich, H.²

29
- 0027751708
- W. Lai, and O.R. Martin Carbohydr. Res. 250 1993 185 193
- (1993) Carbohydr. Res. , vol.250 , pp. 185-193
- Lai, W.¹ Martin, O.R.²

30
- 0030952760
- B.A. Johns, Y.T. Pan, A.D. Elbein, and C.R. Johnson J. Am. Chem. Soc. 119 1997 4856 4865
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 4856-4865
- Johns, B.A.¹ Pan, Y.T.² Elbein, A.D.³ Johnson, C.R.⁴

31
- 0032803176
- M.A. Leeuwenburgh, S. Picasso, H.S. Overkleeft, G.A. van der Marel, P. Vogel, and J.H. van Boom Eur. J. Org. Chem. 5 1999 1185 1189
- (1999) Eur. J. Org. Chem. , vol.5 , pp. 1185-1189
- Leeuwenburgh, M.A.¹ Picasso, S.² Overkleeft, H.S.³ Van Der Marel, G.A.⁴ Vogel, P.⁵ Van Boom, J.H.⁶

32
- 0032565989
- M. Baudry, V. Barberousse, G. Descotes, R. Faure, J. Pires, and J.-P. Praly Tetrahedron 54 1998 7431 7446
- (1998) Tetrahedron , vol.54 , pp. 7431-7446
- Baudry, M.¹ Barberousse, V.² Descotes, G.³ Faure, R.⁴ Pires, J.⁵ Praly, J.-P.⁶

33
- 0033594237
- O. Tsuruta, H. Yuasa, S. Kurono, and H. Hashimoto Bioorg. Med. Chem. Lett. 9 1999 807 810
- (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 807-810
- Tsuruta, O.¹ Yuasa, H.² Kurono, S.³ Hashimoto, H.⁴

34
- 0027433739
- H. Yuasa, S. Kurono, and H. Hashimoto Tetrahedron 49 1993 8977 8998
- (1993) Tetrahedron , vol.49 , pp. 8977-8998
- Yuasa, H.¹ Kurono, S.² Hashimoto, H.³

35
- 0038066180
- W. Zou, E. Lacroix, Z. Wang, and S.-H. Wu Tetrahedron Lett. 44 2003 4431 4433
- (2003) Tetrahedron Lett. , vol.44 , pp. 4431-4433
- Zou, W.¹ Lacroix, E.² Wang, Z.³ Wu, S.-H.⁴

36
- 0000375543
- M.A. Thome, M.B. Giudicelli, D. Picq, and D. Anker J. Carbohydr. Chem. 10 1991 923 926
- (1991) J. Carbohydr. Chem. , vol.10 , pp. 923-926
- Thome, M.A.¹ Giudicelli, M.B.² Picq, D.³ Anker, D.⁴

37
- 4243620067
- B. Capon Chem. Rev. 69 1969 407 498
- (1969) Chem. Rev. , vol.69 , pp. 407-498
- Capon, B.¹

38
- 0035975152
- W. Zou, Z. Wang, E. Lacroix, S.-H. Wu, and H. Jennings Carbohydr. Res. 334 2001 223 231
- (2001) Carbohydr. Res. , vol.334 , pp. 223-231
- Zou, W.¹ Wang, Z.² Lacroix, E.³ Wu, S.-H.⁴ Jennings, H.⁵

39
- 0029059054
- T. Uchiyama, V.P. Vassilev, T. Kajimoto, W. Wong, H. Huang, C.-C. Lin, and C.-H. Wong J. Am. Chem. Soc. 117 1995 5395 5396
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 5395-5396
- Uchiyama, T.¹ Vassilev, V.P.² Kajimoto, T.³ Wong, W.⁴ Huang, H.⁵ Lin, C.-C.⁶ Wong, C.-H.⁷

40
- 0030796701
- T.G. Minehan, and Y. Kishi Tetrahedron Lett. 38 1997 6815 6818
- (1997) Tetrahedron Lett. , vol.38 , pp. 6815-6818
- Minehan, T.G.¹ Kishi, Y.²

41
- 0030710083
- J.-P. Praly, G.-R. Chen, J. Gola, G. Hetzer, and C. Raphoz Tetrahedron Lett. 38 1997 8185 8188
- (1997) Tetrahedron Lett. , vol.38 , pp. 8185-8188
- Praly, J.-P.¹ Chen, G.-R.² Gola, J.³ Hetzer, G.⁴ Raphoz, C.⁵

42
- 0029810354
- B.A. Roe, C.G. Boojamra, J.L. Griggs, and C.R. Bertozzi J. Org. Chem. 61 1996 6442 6445
- (1996) J. Org. Chem. , vol.61 , pp. 6442-6445
- Roe, B.A.¹ Boojamra, C.G.² Griggs, J.L.³ Bertozzi, C.R.⁴

43
- 0001199293
- Y. Araki, N. Kobayashi, K. Watanabe, and Y. Ishido J. Carbohydr. Chem. 4 1985 565 585
- (1985) J. Carbohydr. Chem. , vol.4 , pp. 565-585
- Araki, Y.¹ Kobayashi, N.² Watanabe, K.³ Ishido, Y.⁴

44
- 0037070589
- H. Shao, Z. Wang, E. Laroix, S.-H. Wu, H. Jennings, and W. Zou J. Am. Chem. Soc. 124 2002 2130 2131
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 2130-2131
- Shao, H.¹ Wang, Z.² Laroix, E.³ Wu, S.-H.⁴ Jennings, H.⁵ Zou, W.⁶

45
- 0142090168
- Z. Wang, H. Shao, E. Laroix, S.-H. Wu, H. Jennings, and W. Zou J. Org. Chem. 68 2003 8097 8105
- (2003) J. Org. Chem. , vol.68 , pp. 8097-8105
- Wang, Z.¹ Shao, H.² Laroix, E.³ Wu, S.-H.⁴ Jennings, H.⁵ Zou, W.⁶

46
- 0029882333
- J.P. McDevitt, and P.T. Lansbury J. Am. Chem. Soc. 118 1996 3818 3828
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 3818-3828
- McDevitt, J.P.¹ Lansbury, P.T.²

47
- 0000768939
- R.D. Dawe, and B. Fraser-Reid J. Org. Chem. 49 1984 522 528
- (1984) J. Org. Chem. , vol.49 , pp. 522-528
- Dawe, R.D.¹ Fraser-Reid, B.²

48
- 0027113990
- L. Dheilly, C. Frechou, D. Beaupere, R. Uzan, and G. Demailly Carbohydr. Res. 224 1992 301 306
- (1992) Carbohydr. Res. , vol.224 , pp. 301-306
- Dheilly, L.¹ Frechou, C.² Beaupere, D.³ Uzan, R.⁴ Demailly, G.⁵

49
- 37049098669
- J.R. Pougny, M.A.M. Nassr, and P. Sinaÿ J. Chem. Soc., Chem. Commun. 1981 375 376
- (1981) J. Chem. Soc., Chem. Commun. , pp. 375-376
- Pougny, J.R.¹ Nassr, M.A.M.² Sinaÿ, P.³

50
- 0016844483
- H. Orhui, G.H. Jones, J.G. Moffat, M.L. Maddox, A.T. Christensen, and S.K. Byram J. Am. Chem. Soc. 97 1975 4602 4613
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 4602-4613
- Orhui, H.¹ Jones, G.H.² Moffat, J.G.³ Maddox, M.L.⁴ Christensen, A.T.⁵ Byram, S.K.⁶

51
- 0008719663
- S. Hanessian, T. Ogawa, and Y. Guindon Carbohydr. Res. 38 1974 C12 14
- (1974) Carbohydr. Res. , vol.38
- Hanessian, S.¹ Ogawa, T.² Guindon, Y.³

52
- 0035821342
- H. Yuasa, J. Takada, and H. Hashimoto Bioorg. Med. Chem. Lett. 11 2001 1137 1139
- (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 1137-1139
- Yuasa, H.¹ Takada, J.² Hashimoto, H.³

53
- 0028019656
- H. Yuasa, T. Kajimoto, and C.-H. Wong Tetrahedron Lett. 35 1994 8243 8246
- (1994) Tetrahedron Lett. , vol.35 , pp. 8243-8246
- Yuasa, H.¹ Kajimoto, T.² Wong, C.-H.³

54
- 12144270957
- London, Ontario, Canada, May 29-June 1 Abstr. 471
- Similar results were also obtained by Szezepina, M. G.; Pinto, B. M. 87th Canadian Chemical Conference and Exhibition, London, Ontario, Canada, May 29-June 1, 2004; Abstr. 471
- (2004) 87th Canadian Chemical Conference and Exhibition
- Szezepina, M.G.¹ Pinto, B.M.²

55
- 0034623528
- L. Svansson, B.D. Johnston, J.-H. Gu, B. Patrick, and B.M. Pinto J. Am. Chem. Soc. 122 2000 10769 10775
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 10769-10775
- Svansson, L.¹ Johnston, B.D.² Gu, J.-H.³ Patrick, B.⁴ Pinto, B.M.⁵

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