-
3
-
-
0025572709
-
-
(a) Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130.
-
(1990)
Science
, vol.250
, pp. 1130
-
-
Phillips, M.L.1
Nudelman, E.2
Gaeta, F.C.A.3
Perez, M.4
Singhal, A.K.5
Hakomori, S.6
Paulson, J.C.7
-
4
-
-
0026445723
-
-
(b) Lasky, L. A. Science 1992, 258, 964.
-
(1992)
Science
, vol.258
, pp. 964
-
-
Lasky, L.A.1
-
7
-
-
0028082177
-
-
(e) Yuen, C.-T.; Bezouska, K.; O'brien, J.; Stoll, M.; Lemoine, R.; Lubineau, A.; Kiso, M.; Hasegava, A.; Bockovich, N. J.; Nicolaou, K. C.; Feizi, T. J. Biol. Chem. 1994, 269, 1595.
-
(1994)
J. Biol. Chem.
, vol.269
, pp. 1595
-
-
Yuen, C.-T.1
Bezouska, K.2
O'Brien, J.3
Stoll, M.4
Lemoine, R.5
Lubineau, A.6
Kiso, M.7
Hasegava, A.8
Bockovich, N.J.9
Nicolaou, K.C.10
Feizi, T.11
-
9
-
-
0008897689
-
-
Garegg, P. J., Lindberg, A. A., Eds.; ACS Symposium Series 519; American Chemical Society; Washington, DC
-
(b) Meldal, M.; Mouritsen, S.; Bock, K. In Carbohydrate Antigens; Garegg, P. J., Lindberg, A. A., Eds.; ACS Symposium Series 519; American Chemical Society; Washington, DC, 1993; p 19.
-
(1993)
Carbohydrate Antigens
, pp. 19
-
-
Meldal, M.1
Mouritsen, S.2
Bock, K.3
-
11
-
-
0025102915
-
-
For recent review articles on oligosaccharide synthesis, see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823-839. (b) Banoub, J. Chem. Rev. 1992, 92, 1167-1195. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
-
(1990)
Angew. Chem., Int. Ed. Engl.
, vol.29
, pp. 823-839
-
-
Paulsen, H.1
-
12
-
-
0000198772
-
-
For recent review articles on oligosaccharide synthesis, see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823-839. (b) Banoub, J. Chem. Rev. 1992, 92, 1167-1195. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
-
(1992)
Chem. Rev.
, vol.92
, pp. 1167-1195
-
-
Banoub, J.1
-
13
-
-
5244279498
-
-
For recent review articles on oligosaccharide synthesis, see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823-839. (b) Banoub, J. Chem. Rev. 1992, 92, 1167-1195. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
-
(1993)
Chem. Rev.
, vol.93
, pp. 1503
-
-
Toshima, K.1
Tatsuta, K.2
-
14
-
-
0028186224
-
-
For recent review articles on oligosaccharide synthesis, see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823-839. (b) Banoub, J. Chem. Rev. 1992, 92, 1167-1195. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
-
(1994)
Adv. Carbohydr. Chem. Biochem.
, vol.50
, pp. 21
-
-
Schmidt, R.R.1
Kinzy, W.2
-
15
-
-
0029739240
-
-
For recent review articles on oligosaccharide synthesis, see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823-839. (b) Banoub, J. Chem. Rev. 1992, 92, 1167-1195. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
-
(1996)
Angew. Chem., Int. Ed. Engl.
, vol.35
, pp. 1380
-
-
Danishefsky, S.J.1
Bilodeau, M.T.2
-
16
-
-
85022498621
-
-
(a) Fraser-Reid, B.; Udodong, U. E.; Wu, Z.; Ottosson, H.; Merritt, J. R.; Rao, C. S.; Roberts, C. Synlett 1992, 927.
-
(1992)
Synlett
, pp. 927
-
-
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
-
18
-
-
0028243331
-
-
(c) Yamada, H.; Harada, T.; Miyazaki, H.; Takahashi, T. Tetrahedron Lett. 1994, 35, 3979.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 3979
-
-
Yamada, H.1
Harada, T.2
Miyazaki, H.3
Takahashi, T.4
-
19
-
-
0001632624
-
-
(d) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7919.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 7919
-
-
Yamada, H.1
Harada, T.2
Takahashi, T.3
-
21
-
-
33748597918
-
-
(f) Ley, S. V.; Priepke, H. W. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2292.
-
(1994)
Angew. Chem., Int. Ed. Engl.
, vol.33
, pp. 2292
-
-
Ley, S.V.1
Priepke, H.W.M.2
-
22
-
-
33751375591
-
-
(g) Grice, P.; Ley, S. V.; Pietruszka, J.; Priepke, H. W. M.; Walther, E. P. E. Synlett 1995, 781.
-
(1995)
Synlett
, pp. 781
-
-
Grice, P.1
Ley, S.V.2
Pietruszka, J.3
Priepke, H.W.M.4
Walther, E.P.E.5
-
23
-
-
0000469759
-
-
(h) Geurtsen, R.; Holmes, D. S.; Boons, G.-J. J. Org. Chem. 1997, 62, 8145.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 8145
-
-
Geurtsen, R.1
Holmes, D.S.2
Boons, G.-J.3
-
24
-
-
0030892662
-
-
(i) Grice, P.; Ley, S. V.; Pietruszka, J.; Osborn, M. I.; Henning, W. M.; Priepke, H. W. M.; Warriner, S. L. Chem. Eur. J. 1997, 431.
-
(1997)
Chem. Eur. J.
, pp. 431
-
-
Grice, P.1
Ley, S.V.2
Pietruszka, J.3
Osborn, M.I.4
Henning, W.M.5
Priepke, H.W.M.6
Warriner, S.L.7
-
25
-
-
26844574035
-
-
Green, L.; Hinzen, B.; Ince, S. J.; Langer, P.; Lev, S. V.; Warriner, S. L. Synlett 1998, 4, 440.
-
(1998)
Synlett
, vol.4
, pp. 440
-
-
Green, L.1
Hinzen, B.2
Ince, S.J.3
Langer, P.4
Lev, S.V.5
Warriner, S.L.6
-
26
-
-
33748601612
-
-
For quantitative analysis of the glycosylation reactivity of several glycosyl donors using NMR, see the leading work: Douglas, N. L.; Ley S. V.; Lucking, U.; Warriner, S. L. J. Chem. Soc., Perkin Trans. 1 1998, 51.
-
(1998)
J. Chem. Soc., Perkin Trans. 1
, pp. 51
-
-
Douglas, N.L.1
Ley, S.V.2
Lucking, U.3
Warriner, S.L.4
-
27
-
-
37849189010
-
-
For a recent review on the synthesis and application of thioglycosides, see: Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179.
-
(1997)
Adv. Carbohydr. Chem. Biochem.
, vol.52
, pp. 179
-
-
Garegg, P.J.1
-
28
-
-
0025309559
-
-
(a) Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 4313
-
-
Konradsson, P.1
Udodong, U.E.2
Fraser-Reid, B.3
-
29
-
-
0025125757
-
-
(b) Veeneman, G. H.; van Leuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 1331
-
-
Veeneman, G.H.1
Van Leuwen, S.H.2
Van Boom, J.H.3
-
34
-
-
0031465387
-
-
(g) Burkart, M. D.; Zhang, Z.; Hung, S.-C.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11743.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 11743
-
-
Burkart, M.D.1
Zhang, Z.2
Hung, S.-C.3
Wong, C.-H.4
-
35
-
-
0001501743
-
-
Pinkernell, U.; Karst, U.; Cammann, K. Anal. Chem. 1994, 66, 2599.
-
(1994)
Anal. Chem.
, vol.66
, pp. 2599
-
-
Pinkernell, U.1
Karst, U.2
Cammann, K.3
-
36
-
-
0027538622
-
-
Kahne, D.; Walker, S.; Cheng, Y.; Van Engen, D. J. Am. Chem. Soc. 1993, 115, 1580.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 1580
-
-
Kahne, D.1
Walker, S.2
Cheng, Y.3
Van Engen, D.4
-
38
-
-
0021135638
-
-
(b) Nicolaou, K. C.; Dolle, R. D.; Papahatjis, D. P.; Randall, J. L. J. Am. Chem. Soc. 1984, 106, 4189.
-
(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 4189
-
-
Nicolaou, K.C.1
Dolle, R.D.2
Papahatjis, D.P.3
Randall, J.L.4
-
39
-
-
0003130722
-
-
(a) Sato, S.; Mori, M.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1986, 155, C6.
-
(1986)
Carbohydr. Res.
, vol.155
-
-
Sato, S.1
Mori, M.2
Ito, Y.3
Ogawa, T.4
-
40
-
-
0001102301
-
-
(b) Anderson, F. O.; Fugedi, P.; Garegg, P. J.; Nashed, M. Tetrahedron Lett. 1986, 27, 3919.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 3919
-
-
Anderson, F.O.1
Fugedi, P.2
Garegg, P.J.3
Nashed, M.4
-
43
-
-
12444311462
-
-
Fraser-Reid, B.; Wu, Z.; Udodong, U. E.; Ottosson, H. J. Org. Chem. 1990, 55, 6068.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 6068
-
-
Fraser-Reid, B.1
Wu, Z.2
Udodong, U.E.3
Ottosson, H.4
-
44
-
-
13044310031
-
-
note
-
A precise measurement with DMTST is difficult as its efficiency for the activation is lower than that of NIS: normally 4 equiv of DMTST is used for the glycosylation and the reaction is much slower than that of NIS. We observed that 2 equiv could be enough to complete a reaction with 1 equiv of thioglycoside within a certain time. For the competition reactions, the conditions were exactly the same as those with NIS-TfOH (see general procedure in Experimental Section), except that DMTST was taken as 2 mole equiv relative to the donors (each I mole equiv) and the reaction was continued for 3 h. This measurement can only be performed between donors with small reactivity differences.
-
-
-
-
46
-
-
0000023645
-
-
Miljkovic, M.; Yeagley, D.; Deslongchamps, P.; Dory, Y. L. J. Org. Chem. 1997, 62, 7597.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 7597
-
-
Miljkovic, M.1
Yeagley, D.2
Deslongchamps, P.3
Dory, Y.L.4
-
47
-
-
13044284050
-
-
note
-
The elevated reactivity of N-Troc-protected glucosamines might be the result of the electron-donating property of the N-trichloroethoxycarbonyl group to stabilize the intermediate as shown in the following tentative mechanism. Research is underway to test the proposal.
-
-
-
-
52
-
-
0039579432
-
-
(e) Paulsen, H.; Richter, A.; Sinnwell, H.; Stenzel, W. Carbohydr. Res. 1974, 38, 312.
-
(1974)
Carbohydr. Res.
, vol.38
, pp. 312
-
-
Paulsen, H.1
Richter, A.2
Sinnwell, H.3
Stenzel, W.4
-
53
-
-
0032558124
-
-
Wong, C.-H.; Ye, X.-S.; Zhang, Z. J. Am. Chem. Soc. 1998, 120, 7137.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 7137
-
-
Wong, C.-H.1
Ye, X.-S.2
Zhang, Z.3
-
54
-
-
13044289928
-
-
note
-
For example, in the synthesis of the lactoside 9 (see scheme below), in addition to the target disaccharide 9 (65%), the succinimide product 58 (15%) was also isolated as a byproduct.
-
-
-
-
55
-
-
13044305171
-
-
note
-
48 (1776) 9 (6.9) 58 2.0 equiv 65% 15% The low reactivity of the 4-OH of glucoside 10 (RRV = 8.4), coupled with an increased reactivity of the transient intermediate cation derived from the initial reaction of galactoside 48 (RRV = 1776) with iodonium ion, could explain the formation of 57.
-
-
-
-
56
-
-
21844520164
-
-
(a) Balavoine, G., Berteina, S.; Gret, A.; Fischer, J.; Lubineau, A. J. Carbohydr. Chem. 1995, 14, 1217.
-
(1995)
J. Carbohydr. Chem.
, vol.14
, pp. 1217
-
-
Balavoine, G.1
Berteina, S.2
Gret, A.3
Fischer, J.4
Lubineau, A.5
-
58
-
-
0031465387
-
-
(c) Burkart, M. D.; Zhang, Z.; Huang, S.-C.; Wong, C.-H. J Am. Chem. Soc. 1997, 119, 11743.
-
(1997)
J Am. Chem. Soc.
, vol.119
, pp. 11743
-
-
Burkart, M.D.1
Zhang, Z.2
Huang, S.-C.3
Wong, C.-H.4
-
59
-
-
0028840018
-
-
(d) DeNinno, M. P.; Etienne, J. B.; Duplantier, K. C. Tetrahedron Lett. 1995, 36, 669.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 669
-
-
DeNinno, M.P.1
Etienne, J.B.2
Duplantier, K.C.3
-
60
-
-
0000212407
-
-
Nilsson, U.; Ray, R. K.; Magnusson, G. Carbohydr. Res. 1990, 208, 260.
-
(1990)
Carbohydr. Res.
, vol.208
, pp. 260
-
-
Nilsson, U.1
Ray, R.K.2
Magnusson, G.3
-
61
-
-
37049082264
-
-
Vargas-Berenauel, A.; Meldal, M.; Paulsen, H.; Jensen, K. J.; Bock, K. J. Chem. Soc., Perkin Trans 1 1994, 3287.
-
(1994)
J. Chem. Soc., Perkin Trans 1
, pp. 3287
-
-
Vargas-Berenauel, A.1
Meldal, M.2
Paulsen, H.3
Jensen, K.J.4
Bock, K.5
-
62
-
-
0024772634
-
-
Luening, B.; Norberg, T.; Tejbrant, J. Glycoconjugate J. 1989, 6, 5-19.
-
(1989)
Glycoconjugate J.
, vol.6
, pp. 5-19
-
-
Luening, B.1
Norberg, T.2
Tejbrant, J.3
-
63
-
-
0025708097
-
-
Boullanger, P.; Jouineau, M.; Bouammal, B.; Lafont, D.; Descotes, G. Carbohydr. Res. 1990, 202, 151.
-
(1990)
Carbohydr. Res.
, vol.202
, pp. 151
-
-
Boullanger, P.1
Jouineau, M.2
Bouammal, B.3
Lafont, D.4
Descotes, G.5
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