Synthesis of Two d‐Glucosamine Derived 3,4‐Epoxides as Potential Scaffolds for Combinatorial Chemistry

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Acknowledgments

We thank Mrs. Lene Kastrup for preparation of some intermediates and Dr. Klaus Gundertofte for valuable discussions. A Bøje Benzon Fellowship from the Alfred Benzon Foundation to KJJ is gratefully acknowledged.

Notes

^aSelected ¹H chemical shifts, δ, in ppm (coupling constants in Hz to the following ¹H) for 7: H‐1, 4.58 (4.9); H‐2, 3.14 (2.2); H‐3, 3.31 (4.7); H‐4, 3.45 (0.6); H‐5, 3.92 (4.7); H‐6 3.88 (m).

^bSelected ¹H chemical shifts, δ, in ppm (coupling constants in Hz to the following ¹H) (δ, J) for 11: H‐1 4.47 (4.3 Hz); H‐2 2.97 (4.5); H‐3 and H‐4 3.29‐3.34; H‐5 3.94 (t, 7.1 Hz); H‐6a 3.74 (dd, 6.3 Hz, 10.5 Hz); H‐6b 3.65 (3.9 Hz, 9.9 Hz).

^cSelected ¹H chemical shifts, δ, in ppm (coupling constants in Hz to the following ¹H) (δ, J) for 12a: H‐1 4.76 (3.0 Hz); H‐2 2.84 (10.2 Hz); H‐3 4.13 (10.7); H‐4 3.00 (11.1 Hz); H‐5 3.70; H‐6a 3.97 (11.1 Hz, 1.7 Hz); J‐6b 3.86 (5.1Hz).

^dSelected ¹H chemical shifts, δ, in ppm (coupling constants in Hz to the following ¹H) (δ, J) for 12b: H‐1 4.73 (3.0 Hz); H‐2 2.75 (10.2 Hz); H‐3 4.10 (10.7); H‐4 2.57 (10.7 Hz); H‐5 3.64; H‐6a 3.96 (11.3 Hz, 1.7 Hz); J‐6b 3.81 (5.5 Hz).