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34248562794
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The anomers of 3,4-trans-3a could not be separated by flash chromatography and their stereochemistry was attributed on the basis of the coupling constants and through NOE experiments. The major anomer showed that the methyl group at 5-position was cis to the proton at C4. For NMR determination of similar structures, see: (a) Yong, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.; White, A. H. Tetrahedron 2007, 63, 5579.
-
The anomers of 3,4-trans-3a could not be separated by flash chromatography and their stereochemistry was attributed on the basis of the coupling constants and through NOE experiments. The major anomer showed that the methyl group at 5-position was cis to the proton at C4. For NMR determination of similar structures, see: (a) Yong, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.; White, A. H. Tetrahedron 2007, 63, 5579.
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Fiumana, A.1
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-
52
-
-
55449134853
-
-
3a: Major anomer: 1H NMR (600 MHz, C6D 6, δ, 0.82 (d, 3 H, J, 6.6 Hz, 0.93 (t, 3 H, J, 7.2 Hz, 0.97 (d, 3 H, J, 6.6 Hz, 1.51 (s, 3 H, 1.64 (m, 1 H, 2.83 (d, 1 H, J, 5.4 Hz, 3.58 (dd, 1 H, J, 5.4, 7.2 Hz, 3.93 (m, 1 H, 3.98 (m, 1 H, 13C NMR (75 MHz, CDCl3, 5= 14.1, 18.7, 19.4, 23.8, 32.6, 60.1, 61.3, 67.9, 106.5, 170.7. Minor anomer: 1H NMR (600 MHz, C6D6, δ, 0.86 (d, 3 H, J, 7.2 Hz, 0.88 (d, 3 H, J, 6.6 Hz, 0.91 (t, 3 H, J, 7.2 Hz, 1.45 (s, 3 H, 1.50 (m, 1 H, 3.03 (d, 1 H, J, 7.8 Hz, 3.88 (dd, 1 H, J, 7.2, 7.8 Hz, 3.92 (m, 2 H, 13C NMR 75 MHz, CDCl3, δ, 14.2, 19.6, 20.4, 22.2, 30.1, 61.1, 62.0, 71.9, 108.4, 171.5
-
3): δ = 14.2, 19.6, 20.4, 22.2, 30.1, 61.1, 62.0, 71.9, 108.4, 171.5.
-
-
-
-
53
-
-
55449125318
-
-
3): δ = 10.6, 14.1, 22.4, 29.4, 61.0, 131.3, 143.9, 154.4, 167.5.
-
3): δ = 10.6, 14.1, 22.4, 29.4, 61.0, 131.3, 143.9, 154.4, 167.5.
-
-
-
-
54
-
-
55449126233
-
-
3): δ = 14.0, 17.6, 18.7, 25.1, 33.3, 37.6, 61.0, 61.6, 65.1, 109.8, 167.5.
-
3): δ = 14.0, 17.6, 18.7, 25.1, 33.3, 37.6, 61.0, 61.6, 65.1, 109.8, 167.5.
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