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The analogous thiophenyl compound 29 was chosen for the large scale synthesis of bromide 33 as a result of the higher crystallinity of the intermediates and over 10 mmol of 29 was prepared under the same reaction conditions and in comparable yields.
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85
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0011173417
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Takeo, K.1
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b) M. Ek, P. J. Garegg, H. Hultberg, S. Oscarson, J. Carbohydr. Chem. 1983, 2, 305-311.
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Ek, M.1
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87
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0025125757
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a) G. H. Veeneman, S. H. van Leeuwen, J. H. van Boom, Tetrahedron Lett. 1990, 31, 1331-1334;
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Tetrahedron Lett.
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Veeneman, G.H.1
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b) P. Konradsson, U. E. Udodong, B. Fraser-Reid, Tetrahedron Lett. 1990, 31, 4313-4316.
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Konradsson, P.1
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-
89
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85007635990
-
-
note
-
9 and 46 were always freshly prepared because migration of the chloroacetate to the 3-hydroxyl was observed upon prolonged standing even at -20°C.
-
-
-
-
90
-
-
0033518559
-
-
Anomeric succinimides have been reported in the literature: Z. Y. Zhang, I. R. Ollmann, X. S. Ye, R. Wischnat, T. Baasov, C.-H. Wong, J. Am. Chem. Soc. 1999, 121, 734-753.
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Zhang, Z.Y.1
Ollmann, I.R.2
Ye, X.S.3
Wischnat, R.4
Baasov, T.5
Wong, C.-H.6
-
93
-
-
0026523041
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b) A. G. Kutateladze, J. L. Kice, T. G. Kutateladze, N. S. Zefirov, N. V. Zyk, Tetrahedron Lett. 1992, 33, 1949-1952.
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Tetrahedron Lett.
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-
-
Kutateladze, A.G.1
Kice, J.L.2
Kutateladze, T.G.3
Zefirov, N.S.4
Zyk, N.V.5
-
95
-
-
0030768522
-
-
b) methyl di-tert-butylpyridine can be added as acid scavenger in this type of coupling: S. J. Danishefsky, S. Hu, P. F. Cirillo, M. Eckhardt, P. H. Seeberger, Chem. Eur. J. 1997, 3, 1617-1628.
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(1997)
Chem. Eur. J.
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-
-
Danishefsky, S.J.1
Hu, S.2
Cirillo, P.F.3
Eckhardt, M.4
Seeberger, P.H.5
-
96
-
-
85007627950
-
-
note
-
The corresponding fluoride was also prepared and shown to be too unreactive for synthetic use.
-
-
-
-
97
-
-
85007636008
-
-
note
-
It should be noted that TPS deprotection of 47 with HF · pyridine was slow and low yielding while TBAF treatment led to removal of the chloroacetate groups.
-
-
-
-
101
-
-
85086751471
-
-
note
-
3 solutions should therefore never be evaporated to dryness!
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-
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