✍ Scribed by Russell R. King; Larry A. Calhoun
No coin nor oath required. For personal study only.
N‐acetyl‐4‐nitrotryptophan methyl ester (2), N‐acetyl‐5‐nitrotryptophan methyl ester (3), N‐acetyl‐6‐nitrotryptophan methyl ester (4) and N‐acetyl‐7‐nitrotryptophan methyl ester (5) were synthesized through a modified malonic ester reaction of the appropriate nitrogramine analogs followed by methylation with BF~3~‐methanol. Assignments of the ^1^H and ^13^C NMR chemical shifts were made using a combination of ^1^H–^1^H COSY, ^1^H–^13^C HETCOR and ^1^H–^13^C selective INEPT experiments. Copyright © 2008 Crown in the right of Canada. Published by John Wiley & Sons, Ltd
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Construction of the ether-linked methyl 5aЈ-carba-β-lactoside (3) and N-acetyl-5aЈ-carba-β-lactosaminide (4) were carried out starting from the coupling products 15 and 16, readily obtained by coupling between 1,2-anhydro-4,6-Obenzylidene-5a-carba-D-mannopyranose ( 7) and the oxide anions generated