Tetrahedron letters

Synthesis of (2S, 3R, 4E, 8E)-9-methyl-4, 8-sphingadienine via a novel SN 2′ type reaction mediated by a thioether carbanion

XZ Wang, YL Wu, S Jiang, G Singh

Index: Wang, Xiang-Zhu; Wu, Yu-Lin; Jiang, Shende; Singh, Gurdial Tetrahedron Letters, 1999 , vol. 40, # 50 p. 8911 - 8914

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Citation Number: 8

Abstract

Properties of compound 18: mp 62–63°C. [α] D =−13.8 (c 1.13, CHCl 3 ). IR(KBr)ν max : 3290, 2922, 2852, 1736, 1656, 1553, 1375, 1270 cm −1 . 1 H NMR (300 MHz, CDCl 3 ): δ=5.80 (dt, J=15.2, 6.4 Hz, 1H, H 5 ), 5.65 (d, J=9.1 Hz, 1H, NHAc), 5.42 (dd, J=15.2, 7.4 Hz, 1H, H 4 ), 5.30 (dd, J=7.0, 5.8 Hz, 1H, H 3 ), 5.08 (br, 1H, H 8 ), 4.45 (m, 1H, H 2 ), 4.30 (dd, J=11.6, 6.2 Hz, 1H, H 1 ), 4.05 (dd, J=11.6, 4.1 Hz, 1H, H 1 ), 2.10 (s, 2×3H, OCOCH 3 ), 2.0 ...