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Volumn 10, Issue 12, 2004, Pages 2960-2971

Triisobutylaluminium and dusobutylaluminium hydride as molecular scalpels: The regioselective stripping of perbenzylated sugars and cyclodextrins

(5) Lecourt, Thomas a Herault, Alexandre a Pearce, Alan J a Sollogoub, Matthieu a Sinaÿ, Pierre a

a ECOLE NORMALE SUPÉRIEURE (France)

Author keywords

Carbohydrates; Cyclodextrins; Diisobutylaluminium hydride; Regioselective de O alkylation; Triisobutylaluminium

Indexed keywords

ALKYLATION; ALUMINUM COMPOUNDS; COMPLEXATION; OXYGEN; REACTION KINETICS; SUGARS;

CYCLODEXTRINS; KINETIC FORMATION; MOLECULAR SCALPELS;

HYDRIDES;

ALUMINUM DERIVATIVE; BENZYL DERIVATIVE; CARBOHYDRATE DERIVATIVE; CYCLODEXTRIN; DIISOBUTYLALUMINUM; OXYGEN; REAGENT; TRIISOBUTYLALUMINUM; UNCLASSIFIED DRUG; ALUMINUM; ETHER DERIVATIVE; ORGANOMETALLIC COMPOUND;

ADDITION REACTION; ALKYLATION; ARTICLE; ATOM; BENZYLATION; CHELATION; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL SCALPEL; CHEMICAL STRUCTURE; DE O ALKYLATION; KINETICS; REACTION ANALYSIS; REGIOSELECTIVITY; CHEMISTRY; CONFORMATION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALUMINUM; BENZYL COMPOUNDS; CARBOHYDRATE CONFORMATION; CYCLODEXTRINS; ETHERS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 3042825070 PISSN: 09476539 EISSN: None Source Type: Journal
DOI: 10.1002/chem.200305683 Document Type: Article

Times cited : (154)

References (67)

1
- 0003463148
- Wiley, New York, Chapter 2
- T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed, Wiley, New York, 1999, Chapter 2.
- (1999) Protective Groups in Organic Synthesis, 3rd Ed.
- Greene, T.W.¹ Wuts, P.G.M.²

2
- 0000362728
- D. Beaupère, I. Boutbaiba, A. Wadouachi, C. Frechou, G. Demailly, R. Uzan, New J. Chem. 1992, 16, 405-411.
- (1992) New J. Chem. , vol.16 , pp. 405-411
- Beaupère, D.¹ Boutbaiba, I.² Wadouachi, A.³ Frechou, C.⁴ Demailly, G.⁵ Uzan, R.⁶

3
- 0343427857
- M. C. Cruzado, M. Martin-Lomas, Tetrahedron Lett. 1986, 27, 2497-2500.
- (1986) Tetrahedron Lett. , vol.27 , pp. 2497-2500
- Cruzado, M.C.¹ Martin-Lomas, M.²

4
- 0000373619
- a) R. Allerton, H. G. Fletcher Jr. J. Am. Chem. Soc. 1954, 76, 1757-1760;
- (1954) J. Am. Chem. Soc. , vol.76 , pp. 1757-1760
- Allerton, R.¹ Fletcher Jr., H.G.²

5
- 0001132410
- b) R. Eby, S. J. Sondheimer, C. Schuerch, Carbohydr. Res. 1979, 73, 273-276;
- (1979) Carbohydr. Res. , vol.73 , pp. 273-276
- Eby, R.¹ Sondheimer, S.J.² Schuerch, C.³

6
- 0001920823
- c) J.-I. Sakai, T. Takeda, Y. Ogihara, Carbohydr. Res. 1981, 95, 125-131;
- (1981) Carbohydr. Res. , vol.95 , pp. 125-131
- Sakai, J.-I.¹ Takeda, T.² Ogihara, Y.³

7
- 0025826188
- d) P. Angibeaud, J.-P. Utille, Synthesis 1991, 737-738;
- (1991) Synthesis , pp. 737-738
- Angibeaud, P.¹ Utille, J.-P.²

8
- 0030750991
- e) G. Yang, X. Ding, F. Kong, Tetrahedron Lett. 1997, 38, 6725-6728.
- (1997) Tetrahedron Lett. , vol.38 , pp. 6725-6728
- Yang, G.¹ Ding, X.² Kong, F.³

9
- 0034599360
- J. Madsen, C. Viuf, M. Bols, Chem. Eur. J. 2000, 6, 1140-1146.
- (2000) Chem. Eur. J. , vol.6 , pp. 1140-1146
- Madsen, J.¹ Viuf, C.² Bols, M.³

10
- 0030482135
- a) L. Cipolla, L. Lay, F. Nicotra, Carbohydr. Lett. 1996, 2, 131-135;
- (1996) Carbohydr. Lett. , vol.2 , pp. 131-135
- Cipolla, L.¹ Lay, L.² Nicotra, F.³

11
- 3042847861
- b) L. Cipolla, L. Lay, F. Nicotra, J. Org. Chem. 1996, 61, 6678-6681.
- (1996) J. Org. Chem. , vol.61 , pp. 6678-6681
- Cipolla, L.¹ Lay, L.² Nicotra, F.³

12
- 0000753770
- a) H. Hori, Y. Nishida, H. Ohrui, H. Meguro, J. Org. Chem. 1989, 54, 1346-1353;
- (1989) J. Org. Chem. , vol.54 , pp. 1346-1353
- Hori, H.¹ Nishida, Y.² Ohrui, H.³ Meguro, H.⁴

13
- 0000337399
- b) O. R. Martin, K. G. Kurz, S. P. Rao, J. Org. Chem. 1987, 52, 2922-2925.
- (1987) J. Org. Chem. , vol.52 , pp. 2922-2925
- Martin, O.R.¹ Kurz, K.G.² Rao, S.P.³

14
- 0037017004
- J. R. Falck, D. K. Barma, S. K. Venkataraman, R. Baati, C. Mioskowski, Tetrahedron Lett. 2002, 43, 963-966.
- (2002) Tetrahedron Lett. , vol.43 , pp. 963-966
- Falck, J.R.¹ Barma, D.K.² Venkataraman, S.K.³ Baati, R.⁴ Mioskowski, C.⁵

15
- 0032827825
- A. J. Pearce, M. Sollogoub, J.-M. Mallet, P. Sinaÿ, Eur. J. Org. Chem. 1999, 2103-2117.
- (1999) Eur. J. Org. Chem. , pp. 2103-2117
- Pearce, A.J.¹ Sollogoub, M.² Mallet, J.-M.³ Sinaÿ, P.⁴

16
- 0005609905
- S. K. Das, J.-M. Mallet, P. Sinaÿ, Angew. Chem. 1997, 109, 513-515; Angew. Chem. Int. Ed. Engl. 1997, 36, 493-495.
- (1997) Angew. Chem. , vol.109 , pp. 513-515
- Das, S.K.¹ Mallet, J.-M.² Sinaÿ, P.³

17
- 0030903538
- S. K. Das, J.-M. Mallet, P. Sinaÿ, Angew. Chem. 1997, 109, 513-515; Angew. Chem. Int. Ed. Engl. 1997, 36, 493-495.
- (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 493-495

18
- 0033163821
- M. Sollogoub, S. K. Das, J.-M. Mallet, P. Sinaÿ, C. R. Acad. Sci. Paris, t.2, Série IIc 1999, 441-448.
- (1999) C. R. Acad. Sci. Paris, t.2, Série IIc , pp. 441-448
- Sollogoub, M.¹ Das, S.K.² Mallet, J.-M.³ Sinaÿ, P.⁴

19
- 0037131950
- B. Chevalier-du Roizel, E. Cabianca, P. Rollin, P. Sinaÿ, Tetrahedron 2002, 58, 9579-9583.
- (2002) Tetrahedron , vol.58 , pp. 9579-9583
- Chevalier-Du Roizel, B.¹ Cabianca, E.² Rollin, P.³ Sinaÿ, P.⁴

20
- 0345186660
- A. J. Pearce, P. Sinaÿ, Angew. Chem. 2000, 112, 3756-3758; Angew. Chem. Int. Ed. 2000, 39, 3610-3612.
- (2000) Angew. Chem. , vol.112 , pp. 3756-3758
- Pearce, A.J.¹ Sinaÿ, P.²

21
- 0034675637
- A. J. Pearce, P. Sinaÿ, Angew. Chem. 2000, 112, 3756-3758; Angew. Chem. Int. Ed. 2000, 39, 3610-3612.
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3610-3612

22
- 0037025763
- T. Lecourt, J.-M. Mallet, P. Sinaÿ, Tetrahedron Lett. 2002, 43, 5533-5536.
- (2002) Tetrahedron Lett. , vol.43 , pp. 5533-5536
- Lecourt, T.¹ Mallet, J.-M.² Sinaÿ, P.³

23
- 0345600801
- T. Lecourt, J.-M. Mallet, P. Sinaÿ, Eur. J. Org. Chem. 2003, 4553-4560.
- (2003) Eur. J. Org. Chem. , pp. 4553-4560
- Lecourt, T.¹ Mallet, J.-M.² Sinaÿ, P.³

24
- 0038583942
- T. Lecourt, J.-M. Mallet, P. Sinaÿ, C. R. Chimie 2003, 6, 87-90.
- (2003) C.R. Chimie , vol.6 , pp. 87-90
- Lecourt, T.¹ Mallet, J.-M.² Sinaÿ, P.³

25
- 3042844581
- Nachr. Chem. 2001, 49, 6.
- (2001) Nachr. Chem. , vol.49 , pp. 6

26
- 84981754783
- O. T. Schmidt, T. Auer, H. Schmadel, Chem. Ber. 1960, 93, 556-557.
- (1960) Chem. Ber. , vol.93 , pp. 556-557
- Schmidt, O.T.¹ Auer, T.² Schmadel, H.³

27
- 84985286299
- J. M. Küster, I. Dyong, Liebigs Ann. Chem. 1975, 12, 2179-2189.
- (1975) Liebigs Ann. Chem. , vol.12 , pp. 2179-2189
- Küster, J.M.¹ Dyong, I.²

28
- 84982335996
- F. Weygand, H. Ziemann, Liebigs Ann. Chem. 1962, 657, 179-198.
- (1962) Liebigs Ann. Chem. , vol.657 , pp. 179-198
- Weygand, F.¹ Ziemann, H.²

29
- 37049077300
- K. Naemura, S. Takeuchi, K. Hirose, Y. Tobe, T. Kaneda, Y. Sakata, J. Chem. Soc. Perkin Trans. 1 1995, 213-219.
- (1995) J. Chem. Soc. Perkin Trans. 1 , pp. 213-219
- Naemura, K.¹ Takeuchi, S.² Hirose, K.³ Tobe, Y.⁴ Kaneda, T.⁵ Sakata, Y.⁶

30
- 0028032620
- F. Calvani, P. Crotti, C. Gardelli, M. Pineschi, Tetrahedron 1994, 50, 12999-13022.
- (1994) Tetrahedron , vol.50 , pp. 12999-13022
- Calvani, F.¹ Crotti, P.² Gardelli, C.³ Pineschi, M.⁴

31
- 0001174535
- S. Koto, N. Morishima, R. Kawahara, K. Ishikawa, S. Zen, Bull. Chem. Soc. Jpn. 1982, 55, 1092-1096.
- (1982) Bull. Chem. Soc. Jpn. , vol.55 , pp. 1092-1096
- Koto, S.¹ Morishima, N.² Kawahara, R.³ Ishikawa, K.⁴ Zen, S.⁵

32
- 0009039237
- a) B. C. McKusick, J. Am. Chem. Soc. 1948, 70, 1976-1977;
- (1948) J. Am. Chem. Soc. , vol.70 , pp. 1976-1977
- McKusick, B.C.¹

33
- 0028021978
- b) D. Basavaiah, P. R. Krishna, Tetrahedron 1994, 50, 10521-10530.
- (1994) Tetrahedron , vol.50 , pp. 10521-10530
- Basavaiah, D.¹ Krishna, P.R.²

34
- 0009086037
- a) J.-B. Senderens, J. Aboulenc, C. R. Hebd. Acad. Sci. 1926, 183, 830-832;
- (1926) C. R. Hebd. Acad. Sci. , vol.183 , pp. 830-832
- Senderens, J.-B.¹ Aboulenc, J.²

35
- 0002698479
- b) J. Barluenga, L. Alonso-Cires, P. J. Campos, G. Asensio, Synthesis 1983, 53-55.
- (1983) Synthesis , pp. 53-55
- Barluenga, J.¹ Alonso-Cires, L.² Campos, P.J.³ Asensio, G.⁴

36
- 0011888435
- Y. Rabinsohn, H. G. Fletcher, Jr., J. Org. Chem 1967, 32, 3452-3457.
- (1967) J. Org. Chem. , vol.32 , pp. 3452-3457
- Rabinsohn, Y.¹ Fletcher Jr., H.G.²

37
- 0002917844
- R. Eby, C. Schuerch, Carbohydr. Res. 1974, 34, 79-90.
- (1974) Carbohydr. Res. , vol.34 , pp. 79-90
- Eby, R.¹ Schuerch, C.²

38
- 0030861699
- T. Ooi, N. Kagoshima, K. Maruoka, J. Am. Chem. Soc. 1997, 119, 5754-5755.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 5754-5755
- Ooi, T.¹ Kagoshima, N.² Maruoka, K.³

39
- 0033553140
- T. Ooi, N. Kagoshima, H. Ichikawa, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 3328-3333.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 3328-3333
- Ooi, T.¹ Kagoshima, N.² Ichikawa, H.³ Maruoka, K.⁴

40
- 0032479011
- T. Ooi, D. Uraguchi, N. Kagoshima, K. Maruoka, J. Am. Chem. Soc. 1998, 120, 5327-5328.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 5327-5328
- Ooi, T.¹ Uraguchi, D.² Kagoshima, N.³ Maruoka, K.⁴

41
- 0033537816
- T. Ooi, J. Morikawa, D. Uraguchi, K. Maruoka, Tetrahedron Lett. 1999, 40, 2993-2996.
- (1999) Tetrahedron Lett. , vol.40 , pp. 2993-2996
- Ooi, T.¹ Morikawa, J.² Uraguchi, D.³ Maruoka, K.⁴

42
- 0033038203
- K. Maruoka, T. Ooi, Chem. Eur. J. 1999, 5, 829-833.
- (1999) Chem. Eur. J. , vol.5 , pp. 829-833
- Maruoka, K.¹ Ooi, T.²

43
- 0002487780
- S. Takano, M. Akiyama, S. Sato, K. Ogasawara, Chem. Lett. 1983, 1593-1596.
- (1983) Chem. Lett. , pp. 1593-1596
- Takano, S.¹ Akiyama, M.² Sato, S.³ Ogasawara, K.⁴

44
- 0002669394
- A. Pfaltz, A. Mattenberger, Angew. Chem. 1982, 94, 79; Angew. Chem. Int. Ed. Engl. 1982, 21, 71-72.
- (1982) Angew. Chem. , vol.94 , pp. 79
- Pfaltz, A.¹ Mattenberger, A.²

45
- 0002669394
- A. Pfaltz, A. Mattenberger, Angew. Chem. 1982, 94, 79; Angew. Chem. Int. Ed. Engl. 1982, 21, 71-72.
- (1982) Angew. Chem. Int. Ed. Engl. , vol.21 , pp. 71-72

46
- 33751553123
- M. M. Midland, R. W. Koops, J. Org. Chem. 1990, 55, 5058-5065.
- (1990) J. Org. Chem. , vol.55 , pp. 5058-5065
- Midland, M.M.¹ Koops, R.W.²

47
- 0001726621
- M. Miyashita, M. Hoshino, A. Yoshikoshi, J. Org. Chem. 1991, 56, 6483-6485.
- (1991) J. Org. Chem. , vol.56 , pp. 6483-6485
- Miyashita, M.¹ Hoshino, M.² Yoshikoshi, A.³

48
- 0026730481
- R. Polt, M. A. Peterson, L. DeYoung, J. Org. Chem. 1992, 57, 5469-5480.
- (1992) J. Org. Chem. , vol.57 , pp. 5469-5480
- Polt, R.¹ Peterson, M.A.² DeYoung, L.³

49
- 0027414101
- S. Castellino, D. E. Volk, Tetrahedron Lett. 1993, 34, 967-970.
- (1993) Tetrahedron Lett. , vol.34 , pp. 967-970
- Castellino, S.¹ Volk, D.E.²

50
- 0030841822
- A. Bouzide, G. Sauvé, Tetrahedron Lett. 1997, 30, 5945-5948.
- (1997) Tetrahedron Lett. , vol.30 , pp. 5945-5948
- Bouzide, A.¹ Sauvé, G.²

51
- 0001620721
- S. M. Ludeman, D. L. Bartlett, G. Zon, J. Org. Chem. 1979, 44, 1163-1166.
- (1979) J. Org. Chem. , vol.44 , pp. 1163-1166
- Ludeman, S.M.¹ Bartlett, D.L.² Zon, G.³

52
- 0036159803
- T. Ooi, T. Miura, Y. Itagaki, H. Ichikawa, K. Maruoka, Synthesis 2002, 279-291.
- (2002) Synthesis , pp. 279-291
- Ooi, T.¹ Miura, T.² Itagaki, Y.³ Ichikawa, H.⁴ Maruoka, K.⁵

53
- 0141754483
- V. Sharma, M. Simard, J. D. Wuest, Inorg. Chem. 1991, 30, 579-581.
- (1991) Inorg. Chem. , vol.30 , pp. 579-581
- Sharma, V.¹ Simard, M.² Wuest, J.D.³

54
- 0001675685
- F. Bélanger-Gariépy, K. Hoogsteen, V. Sharma, J. D. Wuest, Inorg. Chem. 1991, 30, 4140-4145.
- (1991) Inorg. Chem. , vol.30 , pp. 4140-4145
- Bélanger-Gariépy, F.¹ Hoogsteen, K.² Sharma, V.³ Wuest, J.D.⁴

55
- 0001989211
- T. Sato, H. Nakamura, Y. Ohno, T. Endo, Carbohydr. Res. 1990, 199, 31-35.
- (1990) Carbohydr. Res. , vol.199 , pp. 31-35
- Sato, T.¹ Nakamura, H.² Ohno, Y.³ Endo, T.⁴

56
- 0038709314
- L. Poorters, D. Armspach, D. Matt, Eur. J. Org. Chem. 2003, 1377-1381.
- (2003) Eur. J. Org. Chem. , pp. 1377-1381
- Poorters, L.¹ Armspach, D.² Matt, D.³

57
- 0017785167
- J.-R. Pougny, J.-C. Jacquinet, M. Nassr, D. Duchet, M.-L. Milat, P. Sinaÿ, J. Am. Chem. Soc. 1977, 99, 6762-6763.
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 6762-6763
- Pougny, J.-R.¹ Jacquinet, J.-C.² Nassr, M.³ Duchet, D.⁴ Milat, M.-L.⁵ Sinaÿ, P.⁶

58
- 0001839713
- W. A. Szarek, H. C. Jarrell, J. K. N. Jones, Carbohydr. Res. 1977, 57, C13-C16.
- (1977) Carbohydr. Res. , vol.57
- Szarek, W.A.¹ Jarrell, H.C.² Jones, J.K.N.³

59
- 0032844913
- S. C. Ennis, A. J. Fairbanks, R. J. Tennant-Eyles, H. S. Yeates, Synlett 1999, 9, 1387-1390.
- (1999) Synlett , vol.9 , pp. 1387-1390
- Ennis, S.C.¹ Fairbanks, A.J.² Tennant-Eyles, R.J.³ Yeates, H.S.⁴

60
- 85023547143
- M. Onaka, M. Kawai, Y. Izumi, Bull. Chem. Soc. Jpn. 1986, 59, 1761-1765.
- (1986) Bull. Chem. Soc. Jpn. , vol.59 , pp. 1761-1765
- Onaka, M.¹ Kawai, M.² Izumi, Y.³

61
- 0001174535
- S. Koto, N. Morishima, R. Kawahara, K. Ishikawa, S. Zen, Bull. Chem. Soc. Jpn. 1982, 55, 1092-1096.
- (1982) Bull. Chem. Soc. Jpn. , vol.55 , pp. 1092-1096
- Koto, S.¹ Morishima, N.² Kawahara, R.³ Ishikawa, K.⁴ Zen, S.⁵

62
- 3042725848
- CAS number 100-72-1
- CAS number 100-72-1.

63
- 0029945546
- Z.-W. Guo, Y.-Z. Hui, Synth. Commun. 1996, 26, 2067-2073.
- (1996) Synth. Commun. , vol.26 , pp. 2067-2073
- Guo, Z.-W.¹ Hui, Y.-Z.²

64
- 0035809374
- W. Wang, A. J. Pearce, Y. Zhang, P. Sinaÿ, Tetrahedron 2001, 12, 517-523.
- (2001) Tetrahedron , vol.12 , pp. 517-523
- Wang, W.¹ Pearce, A.J.² Zhang, Y.³ Sinaÿ, P.⁴

65
- 0031663072
- D. Armspach, D. Matt, Carbohydr. Res. 1998, 310, 129-133.
- (1998) Carbohydr. Res. , vol.310 , pp. 129-133
- Armspach, D.¹ Matt, D.²

66
- 0000835931
- H.-S. Schneider, F. Hacket, V. Rüdiger, Chem. Rev. 1998, 98, 1755-1785.
- (1998) Chem. Rev. , vol.98 , pp. 1755-1785
- Schneider, H.-S.¹ Hacket, F.² Rüdiger, V.³

67
- 3042722558
- L. Zervas, C. Zioudrou, J. Am. Chem. Soc. 1956, 78, 214-215.
- (1956) J. Am. Chem. Soc. , vol.78 , pp. 214-215
- Zervas, L.¹ Zioudrou, C.²

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