(3AR,5R)-5-((benzyloxy)methyl)-3a,4,5,7-tetrahydro-3H-pyrano[3,4-c]isoxazole → HCID 131736522, compound

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Reaction Steps

Methyl (2E)-5-cyclopropyl-5-(2,2-diethoxyethoxyl)pent-2-enoate (C34) was converted to the product using the method described for synthesis of 2-{[(2R)-1-(benzyloxy)pent-4-en-2-yl]oxy}-N-hydroxyethanimine (C3) in the section “Alternate conversion of C2 to C4.” The product was obtained as an oil: 1H NMR analysis indicated a roughly 1:1 mixture of geometric isomers around the oxime. Yield: 3.50 g, 15.4 mmol, 73%. 1H NMR (400 MHz, CDCl3) δ 7.73 and 7.47 (2 br s, total 1H), [7.49 (dd, J=5.8, 5.6 Hz) and 6.90 (dd, J=3.7, 3.6 Hz), total 1H], 6.99-7.09 (m, 1H), 5.87-5.93 (m, 1H), [4.54 (dd, half of ABX pattern, J=16.1, 3.6 Hz), 4.37 (dd, half of ABX pattern, J=16.0, 3.7 Hz), 4.28 (dd, half of ABX pattern, J=12.8, 5.5 Hz) and 4.14 (dd, half of ABX pattern, J=12.7, 5.8 Hz), total 2H], 3.74 and 3.74 (2 s, total 3H), 2.71-2.81 (m, 1H), 2.51-2.57 (m, 2H), 0.80-0.90 (m, 1H), 0.63-0.72 (m, 1H), 0.48-0.57 (m, 1H), 0.38-0.47 (m, 1H), 0.06-0.13 (m, 1H).

Provenance & Evidence