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For its use in carbohydrate synthesis, see: ref 12 and the following
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0035859338
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Recently, Herscovici reported the use of this approach to structures related to 2 by a six-step route from triacetyl-D-glucal, see: Herscovici, J.; Egron, M. J.; Quenot, A.; Leclercq, F.; Leforestier, N.; Mignet, N.; Wetzer, B.; Scherman, D. Org. Lett. 2001, 3, 1893-1896.
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This is an improved procedure and yield from our previously published results, see: Bushey, M. L.; Haukaas, M. H.; O'Doherty, G. A J. Org. Chem. 1999, 64, 2984-2985.
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33
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0042910608
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The absolute stereochemistry and the level of enantioexcesses of 3 and 6 were determined by the method of Mosher, see ref 20a
-
The absolute stereochemistry and the level of enantioexcesses of 3 and 6 were determined by the method of Mosher, see ref 20a.
-
-
-
-
34
-
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0041406615
-
-
note
-
Our optimized variation from the typical Sharpless procedure was to the use the sodium salt of N-chlorobenzylcarbamate as the limiting reagent, providing a good yield of a mixture of regioisomers (74%). Thus, the volatile and inexpensively produced vinylfuran in 30% excess allowed for more efficient use of the more costly catalyst and chiral ligand. This procedure routinely provided a ∼40% yield of the furfuryl alcohol 3 and a 21% yield of the TBS-protected regioisomer, see ref 19.
-
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-
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36
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0030577484
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0032541271
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(b) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
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40
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0041407374
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-
In our hands, the TON (turn over numbers) for the catalytic (10%) use of the oxazaborolidine was too low for practical use
-
In our hands, the TON (turn over numbers) for the catalytic (10%) use of the oxazaborolidine was too low for practical use.
-
-
-
-
41
-
-
0029879373
-
-
For catalyst preparation, see
-
(a) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522. For catalyst preparation, see:
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Fujii, A.1
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Noyori, R.5
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42
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0030984352
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(b) Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285-288.
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43
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0035939537
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2H at elevated temperatures (50 °C) with no reduction in enantiopurity and yield, see: Cossy, J.; Eustache, F.; Dalko, P. I. Tetrahedron Lett. 2001, 42, 5005-5007.
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Cossy, J.1
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Dalko, P.I.3
-
44
-
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0042910606
-
-
The preceding reaction sequences have been preformed on both (+)-3 and (-)-3; for simplicity reasons we are only drawing the results for (+)-3
-
The preceding reaction sequences have been preformed on both (+)-3 and (-)-3; for simplicity reasons we are only drawing the results for (+)-3.
-
-
-
-
45
-
-
0041908509
-
-
note
-
By performing the reaction at higher temperatures (0 °C), the minor isomer pivaloate 14β could also be obtained in higher yields as part of a 3:2 ratio, still favoring of the α-anomer 14α. At this point the anomers were separated by medium-pressure liquid chromatography (MPLC, 20% EtOAc/hexanes, UV detection) which produced baseline separation.
-
-
-
-
46
-
-
0042910607
-
-
note
-
A simpler purification procedure resulted by carrying the ∼8% impurity of the minor diastereoisomer through to the reduction step. The β-anomer 14β presumably hydrolyzed when subjected to the Luche conditions; thus when samples of 14α were reduced with small amounts of the β-anomer present, only diastereomerically pure samples of 2 were detected after silica gel chromatography.
-
-
-
-
50
-
-
0042409715
-
-
The relative stereochemistry of the p-nitrobenzoate ester was confirmed by single-crystal X-ray analysis, see Supporting Information
-
The relative stereochemistry of the p-nitrobenzoate ester was confirmed by single-crystal X-ray analysis, see Supporting Information.
-
-
-
-
51
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0030842941
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Donohoe, T. J.; Moore, P. R.; Waring, M. J.; Newcombe, N. J. Tetrahedron Lett. 1997, 38, 5027-5030.
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Moore, P.R.2
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Newcombe, N.J.4
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