SCOPUS 정보 검색 플랫폼

Journal of Organic Chemistry

Volumn 71, Issue 26, 2006, Pages 9658-9671

2,3-Anhydrosugars in glycoside bond synthesis. Application to α-D-galactofuranosides

(2) Bai, Yu a Lowary, Todd L a

a UNIVERSITY OF ALBERTA (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSYL SULFOXIDES; GULOFURANOSYL THIOGLYCOSIDES; OLIGOSACCHARIDES; REGIOSELECTIVITY;

BACTERIOLOGY; CHEMICAL BONDS; ETHERS; POLYSACCHARIDES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

SUGARS;

ACETAL DERIVATIVE; ALPHA DEXTRO GALACTOFURANOSIDE DERIVATIVE; BENZILIC ACID; BENZOIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; EPOXIDE; ESTER DERIVATIVE; ETHER DERIVATIVE; GALACTOSE; GLYCOSIDE; LITHIUM DERIVATIVE; OLIGOSACCHARIDE; SPARTEINE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; BENZYLATION; CARBOHYDRATE SYNTHESIS; CHEMICAL BOND; CONJUGATE; GLYCOSYLATION; QUANTUM YIELD; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY;

CARBOHYDRATE CONFORMATION; GALACTOSIDES; GLYCOSIDES; STEREOISOMERISM;

EID: 33845943260 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo061713o Document Type: Article

Times cited : (66)

References (62)

1
- 0035932033
- Gadikota, R. R.; Callam, C. S.; Lowary, T. L. Org. Lett. 2001, 3, 607-610.
- (2001) Org. Lett , vol.3 , pp. 607-610
- Gadikota, R.R.¹ Callam, C.S.² Lowary, T.L.³

2
- 0037427286
- Gadikota, R. R.; Callam, C. S.; Wagner, T.; Del Fraino, B.; Lowary, T. L. J. Am. Chem. Soc. 2003, 125, 4155-4165.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 4155-4165
- Gadikota, R.R.¹ Callam, C.S.² Wagner, T.³ Del Fraino, B.⁴ Lowary, T.L.⁵

3
- 0742306836
- Cociorva, O. M.; Lowary, T. L. Tetrahedron 2004, 60, 1481-1489.
- (2004) Tetrahedron , vol.60 , pp. 1481-1489
- Cociorva, O.M.¹ Lowary, T.L.²

4
- 0038780848
- Callam, C. S.; Gadikota, R. R.; Lowary, T. L. Synlett 2003, 1271-1274.
- (2003) Synlett , pp. 1271-1274
- Callam, C.S.¹ Gadikota, R.R.² Lowary, T.L.³

5
- 0142245577
- Callam, C. S.; Gadikota, R. R.; Krein, D. M.; Lowary, T. L. J. Am. Chem. Soc. 2003, 125, 13112-13119.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 13112-13119
- Callam, C.S.¹ Gadikota, R.R.² Krein, D.M.³ Lowary, T.L.⁴

6
- 7244245511
- Crich, D.; Chandrasekera, N. S. Angew. Chem., Int. Ed. 2004, 43, 5386-5389.
- (2004) Angew. Chem., Int. Ed , vol.43 , pp. 5386-5389
- Crich, D.¹ Chandrasekera, N.S.²

7
- 77956842701
- Williams, N. R. Adv. Carbohydr. Chem. Biochem. 1970, 25, 109-179.
- (1970) Adv. Carbohydr. Chem. Biochem , vol.25 , pp. 109-179
- Williams, N.R.¹

8
- 0028789599
- (a) de Lederkremer, R. M.; Colli, W. Glycobiology 1995, 5, 547-552.
- (1995) Glycobiology , vol.5 , pp. 547-552
- de Lederkremer, R.M.¹ Colli, W.²

9
- 0035628608
- (b) Houseknecht, J. B.; Lowary, T. L. Curr. Opin. Chem. Biol. 2001, 5, 677-682.
- (2001) Curr. Opin. Chem. Biol , vol.5 , pp. 677-682
- Houseknecht, J.B.¹ Lowary, T.L.²

10
- 0018987662
- Representative examples of α-galactofuranosyl-containing polysaccharides: (a) Hoffman, J.; Lindberg, B.; Glowacka, M.; Derylo, M.; Lorkiewicz, Z. Eur. J. Biochem. 1980, 105, 103-107.
- Representative examples of α-galactofuranosyl-containing polysaccharides: (a) Hoffman, J.; Lindberg, B.; Glowacka, M.; Derylo, M.; Lorkiewicz, Z. Eur. J. Biochem. 1980, 105, 103-107.

11
- 0002015215
- (b) Jansson, P.-E.; Lindberg, B. Carbohydr. Res. 1980, 82, 97-102.
- (1980) Carbohydr. Res , vol.82 , pp. 97-102
- Jansson, P.-E.¹ Lindberg, B.²

12
- 0024383608
- (c) Richards, J. C.; Perry, M. B.; Kniskern, P. J. Can. J. Chem. 1989, 67, 1038-1050.
- (1989) Can. J. Chem , vol.67 , pp. 1038-1050
- Richards, J.C.¹ Perry, M.B.² Kniskern, P.J.³

13
- 0026531909
- (d) Gerwig, G. J.; Kamerling, J. P.; Vliegenthart, J. F. G.; Morag, E.; Lamed, R.; Bayer, E. A. Eur. J. Biochem. 1992, 205, 799-808.
- (1992) Eur. J. Biochem , vol.205 , pp. 799-808
- Gerwig, G.J.¹ Kamerling, J.P.² Vliegenthart, J.F.G.³ Morag, E.⁴ Lamed, R.⁵ Bayer, E.A.⁶

14
- 0027772063
- (e) Gerwig, G. J.; Kamerling, J. P.; Vliegenthart, J. F. G.; Morag, E.; Lamed, R.; Bayer, E. A. J. Biol. Chem. 1993, 268, 26956-26960.
- (1993) J. Biol. Chem , vol.268 , pp. 26956-26960
- Gerwig, G.J.¹ Kamerling, J.P.² Vliegenthart, J.F.G.³ Morag, E.⁴ Lamed, R.⁵ Bayer, E.A.⁶

15
- 0028393188
- (f) Takayanagi, T.; Kimura, A.; Chiba, S.; Ajisaka, K. Carbohydr. Res. 1994, 256, 149-158.
- (1994) Carbohydr. Res , vol.256 , pp. 149-158
- Takayanagi, T.¹ Kimura, A.² Chiba, S.³ Ajisaka, K.⁴

16
- 0028762214
- (g) Parra, E.; Jiménez-Barbero, J.; Bernabé, M.; Leal, J. A.; Prieto, A.; Gómez-Miranda, B. Carbohydr. Res. 1994, 251, 315-325.
- (1994) Carbohydr. Res , vol.251 , pp. 315-325
- Parra, E.¹ Jiménez-Barbero, J.² Bernabé, M.³ Leal, J.A.⁴ Prieto, A.⁵ Gómez-Miranda, B.⁶

17
- 0030983528
- (h) Linnerborg, M.; Wollin, R.; Wildmalm, G. Eur. J. Biochem. 1997, 246, 565-573.
- (1997) Eur. J. Biochem , vol.246 , pp. 565-573
- Linnerborg, M.¹ Wollin, R.² Wildmalm, G.³

18
- 0037047792
- (i) Ahrazem, O.; Prieto, A.; Leal, J. A.; Jiménez-Barbero, J.; Bernabé, M. Carbohydr. Res. 2002, 337, 1503-1506.
- (2002) Carbohydr. Res , vol.337 , pp. 1503-1506
- Ahrazem, O.¹ Prieto, A.² Leal, J.A.³ Jiménez-Barbero, J.⁴ Bernabé, M.⁵

19
- 0242609170
- (j) Ahrazem, O.; Prieto, A.; San-Blas, G.; Leal, J. A.; Jiménez-Barbero, J.; Bernabé, M. Glycobiology 2003, 13, 743-747.
- (2003) Glycobiology , vol.13 , pp. 743-747
- Ahrazem, O.¹ Prieto, A.² San-Blas, G.³ Leal, J.A.⁴ Jiménez-Barbero, J.⁵ Bernabé, M.⁶

20
- 15944422527
- (k) San-Blas, G.; Prieto, A.; Bernabé, M.; Ahrazem, O.; Moreno, B.; Leal, J. A. Med. Mycol. 2005, 43, 153-159.
- (2005) Med. Mycol , vol.43 , pp. 153-159
- San-Blas, G.¹ Prieto, A.² Bernabé, M.³ Ahrazem, O.⁴ Moreno, B.⁵ Leal, J.A.⁶

21
- 0017541699
- Representative examples of α-D-fucofuranosyl-containing polysaccharides: (a) Hoffman, J.; Lindberg, B.; Hofstad, T.; Lygre, H. Carbohydr. Res. 1977, 58, 439-442.
- Representative examples of α-D-fucofuranosyl-containing polysaccharides: (a) Hoffman, J.; Lindberg, B.; Hofstad, T.; Lygre, H. Carbohydr. Res. 1977, 58, 439-442.

22
- 0032871061
- (b) Hanniffy, O. M.; Shashkov, A. S.; Moran, A. P.; Prendergast, M. M.; Senchenkova, S. N.; Knirel, Y. A.; Savage, A. V. Carbohydr. Res. 1999, 319, 124-132.
- (1999) Carbohydr. Res , vol.319 , pp. 124-132
- Hanniffy, O.M.¹ Shashkov, A.S.² Moran, A.P.³ Prendergast, M.M.⁴ Senchenkova, S.N.⁵ Knirel, Y.A.⁶ Savage, A.V.⁷

23
- 0035961427
- (c) Zdorovenko, E. L.; Ovod, V. V.; Zatonsky, G. V.; Shaskov, A. S.; Kocharova, N. A.; Knirel, Y. A. Carbohydr. Res. 2001, 330, 505-510.
- (2001) Carbohydr. Res , vol.330 , pp. 505-510
- Zdorovenko, E.L.¹ Ovod, V.V.² Zatonsky, G.V.³ Shaskov, A.S.⁴ Kocharova, N.A.⁵ Knirel, Y.A.⁶

24
- 0010686805
- (a) Osumi, K.; Enomoto, M.; Sugimura, H. Carbohydr. Lett. 1996, 2, 35-38.
- (1996) Carbohydr. Lett , vol.2 , pp. 35-38
- Osumi, K.¹ Enomoto, M.² Sugimura, H.³

25
- 0031442107
- (b) Gelin, M.; Ferrières, V.; Plusquellec, D. Carbohydr. Lett. 1996, 2, 381-388.
- (1996) Carbohydr. Lett , vol.2 , pp. 381-388
- Gelin, M.¹ Ferrières, V.² Plusquellec, D.³

26
- 0343776948
- (c) Gelin, M.; Ferrières, V.; Plusquellec, D. Eur. J. Org. Chem. 2000, 1423-1431.
- (2000) Eur. J. Org. Chem , pp. 1423-1431
- Gelin, M.¹ Ferrières, V.² Plusquellec, D.³

27
- 30344486997
- Gola, G.; Libenson, P.; Gandolfi-Donadío, L.; Gallo-Rodriguez, C. ARKIVOC 2005, XII, 234-242.
- (2005) ARKIVOC , vol.12 , pp. 234-242
- Gola, G.¹ Libenson, P.² Gandolfi-Donadío, L.³ Gallo-Rodriguez, C.⁴

28
- 33748890866
- Gandolfi-Donadío, L.; Gola, G.; de Lederkremer, R. M.; Gallo-Rodriguez, C. Carbohydr. Res. 2006, 341, 2487-2497.
- (2006) Carbohydr. Res , vol.341 , pp. 2487-2497
- Gandolfi-Donadío, L.¹ Gola, G.² de Lederkremer, R.M.³ Gallo-Rodriguez, C.⁴

29
- 33748947321
- Lee, Y. J.; Lee, B.-Y.; Jeon, H. B.; Kim, K. S. Org. Lett. 2006, 8, 3971-3974.
- (2006) Org. Lett , vol.8 , pp. 3971-3974
- Lee, Y.J.¹ Lee, B.-Y.² Jeon, H.B.³ Kim, K.S.⁴

30
- 0037393350
- Gelin, M.; Ferriéres, V.; Lefeuvre, M.; Plusquellec, D. Eur. J. Org. Chem. 2003, 1285-1293.
- (2003) Eur. J. Org. Chem , pp. 1285-1293
- Gelin, M.¹ Ferriéres, V.² Lefeuvre, M.³ Plusquellec, D.⁴

31
- 26844498306
- Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1765-1767.
- (1994) Angew. Chem., Int. Ed. Engl , vol.33 , pp. 1765-1767
- Ito, Y.¹ Ogawa, T.²

32
- 0027611186
- Sato, N.; Nakazawa, F.; Sato, M.; Hoshino, E.; Ito, T. Carbohydr. Res. 1993, 245, 105-111.
- (1993) Carbohydr. Res , vol.245 , pp. 105-111
- Sato, N.¹ Nakazawa, F.² Sato, M.³ Hoshino, E.⁴ Ito, T.⁵

33
- 33845947732
- Unpublished results
- Callam, C. S.; Lowary, T. L. Unpublished results.
- Callam, C.S.¹ Lowary, T.L.²

34
- 0028810189
- Arasappan, A.; Fraser-Reid, B. Tetrahedron Lett. 1995, 36, 7967-7070.
- (1995) Tetrahedron Lett , vol.36 , pp. 7967-7070
- Arasappan, A.¹ Fraser-Reid, B.²

35
- 0000718023
- D'Accorso, N. B.; Thiel, I. M. E.; Schüller, M. Carbohydr. Res. 1983, 124, 177-184.
- (1983) Carbohydr. Res , vol.124 , pp. 177-184
- D'Accorso, N.B.¹ Thiel, I.M.E.² Schüller, M.³

36
- 33947482643
- Kohn, P.; Samaritano, R. H.; Lerner, L. M. J. Am. Chetn. Soc. 1965, 87, 5475-5480.
- (1965) J. Am. Chetn. Soc , vol.87 , pp. 5475-5480
- Kohn, P.¹ Samaritano, R.H.² Lerner, L.M.³

37
- 28244454733
- Green, J. W.; Pacsu, E. J. Am. Chem. Soc. 1938, 60, 2056-2057.
- (1938) J. Am. Chem. Soc , vol.60 , pp. 2056-2057
- Green, J.W.¹ Pacsu, E.²

38
- 0043174103
- McAuliffe, J. C.; Hindsgaul, O. J. Org. Chem. 1997, 62, 1234-1239.
- (1997) J. Org. Chem , vol.62 , pp. 1234-1239
- McAuliffe, J.C.¹ Hindsgaul, O.²

39
- 0000774393
- Szarek, W. A.; Zamojski, A.; Tiwari, K. N.; Ison, E. R. Tetrahedron Lett. 1986, 27, 3827-3830.
- (1986) Tetrahedron Lett , vol.27 , pp. 3827-3830
- Szarek, W.A.¹ Zamojski, A.² Tiwari, K.N.³ Ison, E.R.⁴

40
- 13244275168
- Madhusudan, S. K.; Misra, A. K. Carbohydr. Res. 2005, 340, 497-502.
- (2005) Carbohydr. Res , vol.340 , pp. 497-502
- Madhusudan, S.K.¹ Misra, A.K.²

41
- 0004288915
- Hanessian, S, Ed, Marcel Dekker: New York
- Norris, P.; Horton, D. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1997; pp 35-52.
- (1997) Preparative Carbohydrate Chemistry , pp. 35-52
- Norris, P.¹ Horton, D.²

42
- 0000203598
- Ferrier, R. J.; Furneaux, R. H. Methods Carbohydr. Chem. 1980, 8, 251-253.
- (1980) Methods Carbohydr. Chem , vol.8 , pp. 251-253
- Ferrier, R.J.¹ Furneaux, R.H.²

43
- 33845185428
- Kahne, D.; Walker, S.; Cheng, Y.; Van Engen, D. J. Am. Chem. Soc. 1989, 111, 6881-6882.
- (1989) J. Am. Chem. Soc , vol.111 , pp. 6881-6882
- Kahne, D.¹ Walker, S.² Cheng, Y.³ Van Engen, D.⁴

44
- 0000794556
- Martin, M. G.; Ganem, B.; Rasmussen, J. R. Carbohydr. Res. 1983, 123, 332-334.
- (1983) Carbohydr. Res , vol.123 , pp. 332-334
- Martin, M.G.¹ Ganem, B.² Rasmussen, J.R.³

45
- 18544381082
- Bai, Y.; Lowary, T. L. Acta Crystallogr., Sect. E 2004, 60, o2201-o2203.
- (2004) Acta Crystallogr., Sect. E , vol.60
- Bai, Y.¹ Lowary, T.L.²

46
- 34547130099
- The ratio of cyclic forms was calculated by the integration of anomeric proton signals in the 1H NMR spectrum, with the peak assignments being made by 1H-1H COSY and HMQC experiments. Assignment of anomeric carbon signals in the 13C NMR spectrum was done by comparison with published data for D-idose (Bock, K, Pedersen, C. Adv. Carbohydr. Chem. Biochem. 1983, 41, 27-66, Anomeric proton resonances: 5.51 ppm (3J1,2, 4.8 Hz, correlated to 13C signal at 97.7 ppm; β-furanose, 5.25 ppm, 3J1,2, 2.6 Hz, correlation to 13C signal at 94.1 ppm; α-pyranose, 5.17 ppm 3J1,2, 2.1 Hz, correlated to 13C signal at 103.5 ppm; a-furanose, 5.08 ppm, 3J1,2, 4.1 Hz, correlation to 13C signal at 95.3 ppm; β-pyranose
- 13C signal at 95.3 ppm; β-pyranose).

47
- 0040284736
- Angyal, S. J. Adv. Carbohydr. Chem. Biochem. 1984, 42, 15-68.
- (1984) Adv. Carbohydr. Chem. Biochem , vol.42 , pp. 15-68
- Angyal, S.J.¹

48
- 33845921871
- H2,H3 = 6.2 Hz, suggesting that other ring conformers are present. Nevertheless, we feel the ratio of cyclic forms can be rationalized by these simple steric arguments.
- H2,H3 = 6.2 Hz, suggesting that other ring conformers are present. Nevertheless, we feel the ratio of cyclic forms can be rationalized by these simple steric arguments.

49
- 0035967761
- Callam, C. S.; Gadikota, R. R.; Lowary, T. L. J. Org. Chem. 2001, 66, 4549-4558.
- (2001) J. Org. Chem , vol.66 , pp. 4549-4558
- Callam, C.S.¹ Gadikota, R.R.² Lowary, T.L.³

50
- 0023575883
- Alcohols 38-40 are commercially available. All others were prepared by reported methods. 41: ref 34. 42: ref 2. 43: Pozsgay, V.; Brisson, J. R.; Jennings, H. J. Can. J. Chem. 1987, 65, 2764-2769.
- Alcohols 38-40 are commercially available. All others were prepared by reported methods. 41: ref 34. 42: ref 2. 43: Pozsgay, V.; Brisson, J. R.; Jennings, H. J. Can. J. Chem. 1987, 65, 2764-2769.

51
- 4644225386
- 44
- 44: Beignet, J.; Tiernan, J.; Woo, C. H.; Kariuki, B. M.; Cox, L. R. J. Org. Chem. 2004, 69, 6341-6356.
- (2004) J. Org. Chem , vol.69 , pp. 6341-6356
- Beignet, J.¹ Tiernan, J.² Woo, C.H.³ Kariuki, B.M.⁴ Cox, L.R.⁵

52
- 0002086064
- 45
- 45: Garegg, P. J.; Hultberg, H.; Wallin, S. Carbohydr. Res. 1982, 108, 97-101.
- (1982) Carbohydr. Res , vol.108 , pp. 97-101
- Garegg, P.J.¹ Hultberg, H.² Wallin, S.³

53
- 0025309559
- Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. 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

54
- 0035913760
- Crich, D.; Smith, M. J. Am. Chem. Soc. 2001, 123, 9015-9020.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 9015-9020
- Crich, D.¹ Smith, M.²

55
- 0029904583
- (a) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239-9248.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 9239-9248
- Yan, L.¹ Kahne, D.²

56
- 0031749791
- (b) Gildersleeve, J.; Pascal, R. A., Jr.; Kahne, D. J. Am. Chem. Soc. 1998, 120, 5961-5969.
- (1998) J. Am. Chem. Soc , vol.120 , pp. 5961-5969
- Gildersleeve, J.¹ Pascal Jr., R.A.² Kahne, D.³

57
- 0033532859
- (c) Gildersleeve, J.; Smith, A.; Sakurai, K.; Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1999, 121, 6176-6182.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 6176-6182
- Gildersleeve, J.¹ Smith, A.² Sakurai, K.³ Raghavan, S.⁴ Kahne, D.⁵

58
- 0030894278
- (a) Crich, D.; Sun, S. J. Org. Chem. 1997, 62, 1198-1199.
- (1997) J. Org. Chem , vol.62 , pp. 1198-1199
- Crich, D.¹ Sun, S.²

59
- 0000734076
- (b) Crich, D.; Sun, S. J. Org. Chem. 1996, 61, 4506-4507.
- (1996) J. Org. Chem , vol.61 , pp. 4506-4507
- Crich, D.¹ Sun, S.²

60
- 0000331250
- Cyr, N.; Perlin, A. S. Can. J. Chem. 1979, 57, 2504-2511.
- (1979) Can. J. Chem , vol.57 , pp. 2504-2511
- Cyr, N.¹ Perlin, A.S.²

61
- 30544437361
- (a) Hodgson, D. M.; Bray, C. D.; Humphreys, P. G. Synlett 2006, 1-22.
- (2006) Synlett , pp. 1-22
- Hodgson, D.M.¹ Bray, C.D.² Humphreys, P.G.³

62
- 33748739693
- (b) Hodgson, D. M.; Lee, G. P.; Marriott, R. E.; Thompson, A. J.; Wisedale, R.; Witherington, J. J. Chem. Soc., Perkin Trans. I 1998, 2151-2161.
- (1998) J. Chem. Soc., Perkin Trans. I , pp. 2151-2161
- Hodgson, D.M.¹ Lee, G.P.² Marriott, R.E.³ Thompson, A.J.⁴ Wisedale, R.⁵ Witherington, J.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.