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During the course of the reaction, the excess alkynyl iodide 12 was reduced to alkyne 11 which could be recovered by flash chromatography.
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29344439891
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The inversed order of reactions, that is, Mitsunobu reaction at the stage of the propargyl alcohol 18 followed by semi-reduction, was much less effective because the Lindlar step did not proceed well likely due to the increased steric hindrance exerted by the adjacent phthalimide residue.
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4-catalyzed process, we confidently ascribe the same stereochemistry to the resulting osmate esters as that observed in 31α and pyranose 32 derived thereof.
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106
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0003089743
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note
-
H-1,H-2 = 7.3 Hz is somewhat ambiguous and could be compatible with either an α- or a β-configuration at the anomeric center; note, however, that the final thioglycoside 33 derived from 32 is α-configured, see Scheme 10.
-
-
-
-
116
-
-
0034641461
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-
J.-C. Thiéry, C. Fréchou, G. Demailly, Tetrahedron Lett. 2000, 41, 6337-6339.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 6337-6339
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-
Thiéry, J.-C.1
Fréchou, C.2
Demailly, G.3
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117
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0040855754
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B. Bernet, T. Mäder, A. Vasella, Helv. Chim. Acta 1997, 80, 1260-1279.
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(1997)
Helv. Chim. Acta
, vol.80
, pp. 1260-1279
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-
Bernet, B.1
Mäder, T.2
Vasella, A.3
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