(R)-2,5,5-Trimethyl-2-(oxiran-2-ylmethyl)-1,3-dioxane
Rf 0.24 (PE: Et2O 5:1);
[α]D25 +8.5 (c 0.43, CHCl3);
IR (neat, cm-1): 3052, 2955, 2984, 2869, 1474, 1412, 1377, 1363, 1349, 1309, 1244, 1211, 1191, 1168, 1121, 1041, 1023, 951, 908, 837, 798, 759, 679;
1H NMR (400 MHz, CDCl3):
δ = 3.28 (2H, d, J = 11.9; H6a, 7a),
3.14 (2H, d, J = 11.9; H6b,7b),
2.78 (1H, dddd, J = 6.3, 5.1, 4.3, 2.7; H2),
2.43 (1H, dd, J = 5.2, 4.3; H1a),
2.15 (1H, dd, J = 5.2, 2.7; H1b),
1.62 (1H, dd, J = 14.3, 5.1; H3a),
1.57 (1H, dd, J = 14.3, 6.3; H3b),
1.15 (3H, s; H5), 0.74 (3H, s; H9),
0.60 (3H, s; H10);
13C NMR (100 MHz, CDCl3):
δ = 97.4 (C4), 69.5 (C6), 69.5 (C7), 47.5 (C2), 45.5 (C1),
40.8 (C3), 29.2 (C8), 22.1 (C9), 21.7 (C10), 19.8 (C5);
HRMS (ESI) calc. for C10H19O3+ [M+H]+ 187.1329, found 187.1321.
