SCOPUS 정보 검색 플랫폼

Chemistry - A European Journal

Volumn 7, Issue 11, 2001, Pages 2382-2389

A highly efficient synthetic strategy for polymeric support synthesis of Lex, Ley, and H-type 2 oligosaccharides

(2) Zhu, Tong a Boons, Geert Jan a

a UNIVERSITY OF GEORGIA (United States)

Author keywords

Glycosylation; Oligosaccharides; Polymeric support; Synthetic methods; Tumor antigens

Indexed keywords

ANTIGENS; ESTERS; PHENOLS; PROTEINS; TUMORS;

POLYMERIC SYNTHESIS;

SYNTHESIS (CHEMICAL);

BENZYL DERIVATIVE; CARBONYL DERIVATIVE; MACROGOL; OLIGOSACCHARIDE; PHENOL DERIVATIVE; POLYMER; TUMOR ANTIGEN;

ARTICLE; BLOOD GROUP LEWIS SYSTEM; CHEMICAL STRUCTURE; CONJUGATION; GLYCOSYLATION; SYNTHESIS;

ABO BLOOD-GROUP SYSTEM; ANTIGENS, CD15; ANTIGENS, TUMOR-ASSOCIATED, CARBOHYDRATE; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CATALYSIS; GLYCOSYLATION; LEWIS BLOOD-GROUP SYSTEM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; POLYETHYLENE GLYCOLS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035354657 PISSN: 09476539 EISSN: None Source Type: Journal
DOI: 10.1002/1521-3765(20010601)7:11<2382::AID-CHEM23820>3.0.CO;2-2 Document Type: Article

Times cited : (45)

References (64)

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

2
- 0030058793
- b) G. J. Boons, Tetrahedron 1996, 52, 1095-1121;
- (1996) Tetrahedron , vol.52 , pp. 1095-1121
- Boons, G.J.¹

3
- 0002767403
- c) G. J. Boons, Contemp. Org. Chem. 1996, 173-200;
- (1996) Contemp. Org. Chem. , pp. 173-200
- Boons, G.J.¹

4
- 0034698451
- d) B. G. Davis, J. Chem. Soc. Perkin Trans. 1 2000, 2137-2160.
- (2000) J. Chem. Soc. Perkin Trans. 1 , pp. 2137-2160
- Davis, B.G.¹

5
- 0001314021
- a) P. Arya, R. N. Ben, Angew. Chem. 1997, 109, 1335-1337;
- (1997) Angew. Chem. , vol.109 , pp. 1335-1337
- Arya, P.¹ Ben, R.N.²

6
- 0030790815
- Angew. Chem. Int. Ed. Engl. 1997, 36, 1280-1282;
- (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1280-1282

7
- 0033152001
- b) F. Schweizer, O. Hindsgaul, Curr. Opin. Chem. Biol. 1999, 2, 291-298;
- (1999) Curr. Opin. Chem. Biol. , vol.2 , pp. 291-298
- Schweizer, F.¹ Hindsgaul, O.²

8
- 0000015941
- c) P. M. St. Hilaire, M. Meldal, Angew. Chem. 2000, 112, 1210-1228;
- (2000) Angew. Chem. , vol.112 , pp. 1210-1228
- St. Hilaire, P.M.¹ Meldal, M.²

9
- 0034599659
- Angew. Chem. Int. Ed. 2000, 39, 1162-1179;
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1162-1179

10
- 0034038967
- d) W. H. Haase, P. H. Seeberger, Curr. Org. Chem. 2000, 4, 481-511.
- (2000) Curr. Org. Chem. , vol.4 , pp. 481-511
- Haase, W.H.¹ Seeberger, P.H.²

11
- 0032558124
- C. H. Wong, X. Ye, Z. Zhang, J. Am. Chem. Soc. 1998, 120, 7137-7138.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 7137-7138
- Wong, C.H.¹ Ye, X.² Zhang, Z.³

12
- 0033998234
- T. Zhu, G. J. Boons, Tetrahedron: Asymmetry 2000, 11, 199-205.
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 199-205
- Zhu, T.¹ Boons, G.J.²

13
- 0034684254
- T. Zhu, G. J. Boons, J. Am. Chem. Soc. 2000, 122, 10222-10223.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 10222-10223
- Zhu, T.¹ Boons, G.J.²

14
- 0033548205
- For a review, see H. M. I. Osborn, T. H. Khan, Tetrahedron 1999, 55, 1807-1850.
- (1999) Tetrahedron , vol.55 , pp. 1807-1850
- Osborn, H.M.I.¹ Khan, T.H.²

15
- 0000462978
- For the recent advances in solid-support oligosaccharide synthesis, see: a) G. H. Veeneman, S. Notemans, R. M. J. Liskamp, G. A. van der Marel, J. H. van Boom, Tetrahedron Lett. 1987, 28, 6695-6698;
- (1987) Tetrahedron Lett. , vol.28 , pp. 6695-6698
- Veeneman, G.H.¹ Notemans, S.² Liskamp, R.M.J.³ Van Der Marel, G.A.⁴ Van Boom, J.H.⁵

16
- 0027591808
- b) S. J. Danishefsky, K. F. McClure, J. T. Randolph, R. B. Ruggeri, Science 1993, 260, 1307-1309;
- (1993) Science , vol.260 , pp. 1307-1309
- Danishefsky, S.J.¹ McClure, K.F.² Randolph, J.T.³ Ruggeri, R.B.⁴

17
- 0002833266
- c) J. T. Randolph, S. J. Danishefsky, Angew. Chem. 1994, 106, 1538-1541;
- (1994) Angew. Chem. , vol.106 , pp. 1538-1541
- Randolph, J.T.¹ Danishefsky, S.J.²

18
- 0002738642
- Angew. Chem. Int. Ed. Engl. 1994, 1470-1473;
- (1994) Angew. Chem. Int. Ed. Engl. , pp. 1470-1473

19
- 0027951227
- d) M. Schulster, P. Wang, J. C. Paulson, C. H. Wong, J. Am. Chem. Soc. 1994, 116, 1135-1136;
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 1135-1136
- Schulster, M.¹ Wang, P.² Paulson, J.C.³ Wong, C.H.⁴

20
- 0000508254
- e) L. Yan, C. M. Taylor, R. Goodnow, Jr., D. Kahne, J. Am. Chem. Soc. 1994, 116, 6593-6594;
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 6593-6594
- Yan, L.¹ Taylor, C.M.² Goodnow Jr., R.³ Kahne, D.⁴

21
- 0029007777
- f) J. T. Randolph, K. F. McClure, S. J. Danishefsky, J. Am. Chem. Soc. 1995, 117, 5712-5719;
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 5712-5719
- Randolph, J.T.¹ McClure, K.F.² Danishefsky, S.J.³

22
- 10544229790
- g) R. Liang, L. Yan, J. Loibach, M. Ge, Y. Uozumi, K. Sekanina, N. Horan, J. Gildersleeve, C. Thompson, A. Smith, K. Biswas, W. C. Still, D. Kahne, Science 1996, 274, 1520-1522;
- (1996) Science , vol.274 , pp. 1520-1522
- Liang, R.¹ Yan, L.² Loibach, J.³ Ge, M.⁴ Uozumi, Y.⁵ Sekanina, K.⁶ Horan, N.⁷ Gildersleeve, J.⁸ Thompson, C.⁹ Smith, A.¹⁰ Biswas, K.¹¹ Still, W.C.¹² Kahne, D.¹³

23
- 0029996782
- h) J. Rademann, R. R. Schmidt, Tetrahedron Lett. 1996, 37, 3989-3990;
- (1996) Tetrahedron Lett. , vol.37 , pp. 3989-3990
- Rademann, J.¹ Schmidt, R.R.²

24
- 0029958313
- i) J. A. Hunt, W. R. Roush, J. Am. Chem. Soc. 1996, 118, 9998-9999;
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 9998-9999
- Hunt, J.A.¹ Roush, W.R.²

25
- 0031048191
- j) K. C. Nicolaou, N. Winssinger, J. Pastor, F. DeRoose, J. Am. Chem. Soc. 1997, 119, 449-450;
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 449-450
- Nicolaou, K.C.¹ Winssinger, N.² Pastor, J.³ DeRoose, F.⁴

26
- 0030684665
- k) R. Rodebaugh, B. Fraser-Reid, H. M. Geysen, Tetrahedron Lett. 1997, 38, 7653-7656;
- (1997) Tetrahedron Lett. , vol.38 , pp. 7653-7656
- Rodebaugh, R.¹ Fraser-Reid, B.² Geysen, H.M.³

27
- 0000932220
- l) J. Rademann, R. R. Schmidt, J. Org. Chem. 1997, 62, 3650-3653;
- (1997) J. Org. Chem. , vol.62 , pp. 3650-3653
- Rademann, J.¹ Schmidt, R.R.²

28
- 0002295513
- m) A. Heckel, E. Mross, K. Jung, J. Rademann, R. R. Schmidt, Synlett 1998, 171-173;
- (1998) Synlett , pp. 171-173
- Heckel, A.¹ Mross, E.² Jung, K.³ Rademann, J.⁴ Schmidt, R.R.⁵

29
- 0001511242
- n) K. C. Nicolaou, N. Watanabe, J. Li, J. Pastor, N. Winssinger, Angew. Chem. 1998, 110, 1636-1638;
- (1998) Angew. Chem. , vol.110 , pp. 1636-1638
- Nicolaou, K.C.¹ Watanabe, N.² Li, J.³ Pastor, J.⁴ Winssinger, N.⁵

30
- 0032547050
- Angew. Chem. Int. Ed. 1998, 37, 1559-1561;
- (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1559-1561

31
- 0000913685
- o) T. Kanemitsu, O. Kanie, C. H. Wong, Angew. Chem. 1998, 110, 3574-3577;
- (1998) Angew. Chem. , vol.110 , pp. 3574-3577
- Kanemitsu, T.¹ Kanie, O.² Wong, C.H.³

32
- 0000835920
- Angew. Chem. Int. Ed. 1998, 37, 3415-3418;
- (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 3415-3418

33
- 0032240244
- p) Y. Ito, S. Manabe, Curr. Opin. Chem. Bio. 1998, 2, 701-708;
- (1998) Curr. Opin. Chem. Bio. , vol.2 , pp. 701-708
- Ito, Y.¹ Manabe, S.²

34
- 0000193352
- q) T. Zhu, G. J. Boons, Angew. Chem. 1998, 110, 2000-2003;
- (1998) Angew. Chem. , vol.110 , pp. 2000-2003
- Zhu, T.¹ Boons, G.J.²

35
- 0032479729
- Angew. Chem. Int. Ed. 1998, 37, 1898-1900;
- (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1898-1900

36
- 0032706852
- r) L. Rnerr, R. R. Schmidt, Synlett 1999, 1802-1804;
- (1999) Synlett , pp. 1802-1804
- Rnerr, L.¹ Schmidt, R.R.²

37
- 0033518044
- s) R. B. Andrade, O. J. Plante, L. G. Melean, P. H. Seeberger, Org. Lett. 1999, 1, 1811-1814;
- (1999) Org. Lett. , vol.1 , pp. 1811-1814
- Andrade, R.B.¹ Plante, O.J.² Melean, L.G.³ Seeberger, P.H.⁴

38
- 0034621990
- t) L. G. Melean, W. Haase, P. H. Seeberger, Tetrahedron Lett. 2000, 41, 4329-4333;
- (2000) Tetrahedron Lett. , vol.41 , pp. 4329-4333
- Melean, L.G.¹ Haase, W.² Seeberger, P.H.³

39
- 0034596459
- u) G. Belogi, T. Zhu, G. J. Boons, Tetrahedron Lett. 2000, 41, 6965-6968;
- (2000) Tetrahedron Lett. , vol.41 , pp. 6965-6968
- Belogi, G.¹ Zhu, T.² Boons, G.J.³

40
- 0034596440
- v) G. Belogi, T. Zhu, G. J. Boons, Tetrahedron Lett. 2000, 41, 6969-6972.
- (2000) Tetrahedron Lett. , vol.41 , pp. 6969-6972
- Belogi, G.¹ Zhu, T.² Boons, G.J.³

41
- 0031098534
- D. J. Gravert, K. D. Janda, Chem. Rev. 1997, 97, 489-509.
- (1997) Chem. Rev. , vol.97 , pp. 489-509
- Gravert, D.J.¹ Janda, K.D.²

42
- 0001686537
- a) S. P. Douglas, D. M. Whitfield, J. T. Krepinsky, J. Am. Chem. Soc. 1991, 113, 5095-5097;
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 5095-5097
- Douglas, S.P.¹ Whitfield, D.M.² Krepinsky, J.T.³

43
- 0001357306
- b) R. Verduyn, P. A. M. van der Klein, G. A. van der Marel, J. H. van Boom, Recl. Trav. Chim. Pays-Bas 1993, 112, 464-465;
- (1993) Recl. Trav. Chim. Pays-Bas , vol.112 , pp. 464-465
- Verduyn, R.¹ Van Der Klein, P.A.M.² Van Der Marel, G.A.³ Van Boom, J.H.⁴

44
- 0028886622
- c) S. P. Douglas, D. M. Whitfield, J. T. Krepinsky, J. Am. Chem. Soc. 1995, 117, 2116-2117.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 2116-2117
- Douglas, S.P.¹ Whitfield, D.M.² Krepinsky, J.T.³

45
- 0032509249
- U. Ellervik, G. Magnusson, J. Org. Chem. 1998, 63, 9314-9322.
- (1998) J. Org. Chem. , vol.63 , pp. 9314-9322
- Ellervik, U.¹ Magnusson, G.²

46
- 0025309559
- a) P. Konradsson, U. E. Udodong, B. Fraser-Reid, Tetrahedron Lett. 1990, 31, 4313-4316;
- (1990) Tetrahedron Lett. , vol.31 , pp. 4313-4316
- Konradsson, P.¹ Udodong, U.E.² Fraser-Reid, B.³

47
- 0025125757
- b) G. H. Veeneman, S. H. van Leeuwen, J. H. van Boom, Tetrahedron Lett. 1990, 31, 1331-1334.
- (1990) Tetrahedron Lett. , vol.31 , pp. 1331-1334
- Veeneman, G.H.¹ Van Leeuwen, S.H.² Van Boom, J.H.³

48
- 0030792355
- X. Zhao, K. D. Janda, Tetrahedron Lett. 1997, 38, 5437-5440.
- (1997) Tetrahedron Lett. , vol.38 , pp. 5437-5440
- Zhao, X.¹ Janda, K.D.²

49
- 0031735591
- M. Benaglia, R. Annunziata, M. Cinquini, F. Cozzi, S. Ressel, J. Org. Chem. 1998, 63, 8628-8629.
- (1998) J. Org. Chem. , vol.63 , pp. 8628-8629
- Benaglia, M.¹ Annunziata, R.² Cinquini, M.³ Cozzi, F.⁴ Ressel, S.⁵

50
- 37049109229
- C. Gioeli, J. B. Chattopadhyaya, J. Chem. Soc. Chem. Commun. 1982, 672-674.
- (1982) J. Chem. Soc. Chem. Commun. , pp. 672-674
- Gioeli, C.¹ Chattopadhyaya, J.B.²

51
- 0016856713
- a) A. Hassner, G. Strand, M. Rubinstein, J. Am. Chem. Soc. 1975, 97, 1614-1615;
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 1614-1615
- Hassner, A.¹ Strand, G.² Rubinstein, M.³

52
- 49549133371
- b) J. H. van Boom, P. M. J. Burgers, Tetrahedron Lett. 1976, 4875-4878.
- (1976) Tetrahedron Lett. , pp. 4875-4878
- Van Boom, J.H.¹ Burgers, P.M.J.²

53
- 0000908358
- T. Zhu, G. J. Boons, Angew. Chem. 1999, 111, 3704-3707;
- (1999) Angew. Chem. , vol.111 , pp. 3704-3707
- Zhu, T.¹ Boons, G.J.²

54
- 0033521192
- Angew. Chem. Int. Ed. 1999, 38, 3495-3497.
- (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3495-3497

55
- 0000477769
- S. J. Danishefsky, J. R. Allen, Angew. Chem. 2000, 112, 882-912;
- (2000) Angew. Chem. , vol.112 , pp. 882-912
- Danishefsky, S.J.¹ Allen, J.R.²

56
- 0034599121
- Angew. Chem. Int. Ed. 2000, 39, 836-863.
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 836-863

57
- 0031723411
- a) S. Hakomori, Acta. Anat. 1998, 161, 79-90;
- (1998) Acta. Anat. , vol.161 , pp. 79-90
- Hakomori, S.¹

58
- 0034596359
- b) P. W. Glunz, S. Hintermann, L. J. Williams, J. B. Schwarz, S. D. Kuduk, V. Kudryashov, K. O. Lloyd, S. J. Danishefsky, J. Am. Chem. Soc. 2000, 122, 7273-7279.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 7273-7279
- Glunz, P.W.¹ Hintermann, S.² Williams, L.J.³ Schwarz, J.B.⁴ Kuduk, S.D.⁵ Kudryashov, V.⁶ Lloyd, K.O.⁷ Danishefsky, S.J.⁸

59
- 0033597612
- L. Jobron, O. Hindsgaul, J. Am. Chem. Soc. 1999, 121, 5835-5836.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 5835-5836
- Jobron, L.¹ Hindsgaul, O.²

60
- 0000815238
- a) R. R. Schmidt, Angew. Chem. 1986, 95, 213-236;
- (1986) Angew. Chem. , vol.95 , pp. 213-236
- Schmidt, R.R.¹

61
- 0022636075
- Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235;
- (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 212-235

62
- 0032391040
- b) L. Manzoni, L. Lay, R. R. Schmidt, J. Carbohydr. Chem. 1998, 739-758.
- (1998) J. Carbohydr. Chem. , pp. 739-758
- Manzoni, L.¹ Lay, L.² Schmidt, R.R.³

63
- 33847576027
- in press
- A. V. Demchenko, G. J. Boons, J. Org. Chem. 2001, 66, in press.
- (2001) J. Org. Chem. , vol.66
- Demchenko, A.V.¹ Boons, G.J.²

64
- 0000462283
- T. B. Windholz, D. B. R. Johnston, M. Sharp, Tetrahedron Lett. 1967, 2555-2557.
- (1967) Tetrahedron Lett. , pp. 2555-2557
- Windholz, T.B.¹ Johnston, D.B.R.² Sharp, M.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.