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15N HMBC spectra were used to assign the connectivity of the imidazole nitrogens with respect to H-(C1′). Diastereoisomers were differentiated by a combination of crystallography and 2D NOESY spectroscopy.
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Equilibration resulting in a 1:4 mixture of 28: 32 is observed over 3 d at 60°C.
-
Equilibration resulting in a 1:4 mixture of 28: 32 is observed over 3 d at 60°C.
-
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39
-
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78649952670
-
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13C HMBC analysis of the products of the reaction of glyceraldehyde, 2, and 5 (see Supporting Information, Figure S28).
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13C HMBC analysis of the products of the reaction of glyceraldehyde, 2, and 5 (see Supporting Information, Figure S28).
-
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40
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C2′ stereochemical inversions have been observed in related molecules under both thermal and photochemical condition; see refs 1, 11b, and 22.
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Proposed six-member imidazole cyclization to furnish 49
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Alternatively, the pH-dependent profiles of the multicomponent reaction described provide a route to 36 - 39 in the presence of 2 and 3. Therefore, subsequent incorporation of the purine fragment with 36, 38, or 39 (or derivatives thereof) still remains a plausible route to purine molecules under prebiotic constraints for their concurrent synthesis with pyrimidine nucleotides accessed via 37.
-
Alternatively, the pH-dependent profiles of the multicomponent reaction described provide a route to 36 - 39 in the presence of 2 and 3. Therefore, subsequent incorporation of the purine fragment with 36, 38, or 39 (or derivatives thereof) still remains a plausible route to purine molecules under prebiotic constraints for their concurrent synthesis with pyrimidine nucleotides accessed via 37.
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