反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
PROCEDURE
实验过程
Compound 78 (1.68 g, 1.5 mmol), octadecanethiol (0.81 g, 2.8 mmol), cesium carbonate (0.50 g, 1.53 mmol) and N,N-dimethylformamide (11 ml) were stirred at room temperature for 7.5 h and worked up as above for 79. The resulting residue was chromatographed (SiO2 -column, 5×18 cm; ethyl acetate:isooctane 2:1 followed by 4:1 and finally ethyl acetate) to give 80 (1.80 g, 91%). Crystallization from methanol gave an analytical sample with mp 150°-152°, [α]D21 +47° (c 0.6, chloroform). 1H-NMR (CDCl3, Me4Si) δ 7.93-7.72 (4H), 5.75 (m, 1H, H3), 5.58 (bd, 1H, J~3 Hz, H4"), 5.42 (d, 1H, J=8 Hz, H1), 5.38 (dd, 1H, J=11 and 3.5 Hz, H2"), 5.16 (dd, 1H, J=11 and 3.5 Hz, H3"), 5.13 (dd, 1H, J=11 and 8 Hz, H2'), 4.98 (d, 1H, J=3.5 Hz, H1"), 4.74 (dd, 1H, J=11 and 2.5 Hz, H3'), 4.63-4.34 (4H, inter alia H1'), 4.58 (d, 1H, J=8 Hz, H1'), 4.29-3.57 (11H), 2.55 (t, 2H, J=7 Hz, CH2S), 2.31 (t, 2H, J=7 Hz, CH2S), 2.15, 2.12, 2.07 (6H), 2.064, 2.058, 2.04, 1.96, 1.95, 1.40-1.15 (bs), 0.88 (t, 3H, J=6.5 Hz, CH3). 13C (CDCl3, Me4Si) δ 170.7, 170.5 (3C), 170.4 170.0, 169.7, 169.5, 168.9, 168.2 (broad, 2C), 134.2 (2C), 134.0 (2C), 123.5 (2C), 101.0 (d, J=160 Hz, Cl' or Cl), 99.6 (d, J=173 Hz, Cl"), 98.1 (d, J=160 Hz, Cl or Cl'), 77.8, 72.7, 72.6, 71.62, 71.56, 69.7 (OCH2CH2), 69.0, 68.8, 67.9, 67.1 (2C), 62.4 (CH2), 61.1 (CH2), 60.2 (CH2), 54.2 (C2), 32.4-22.7 (CH2), 21.0, 20.9, 20.74, 20.68 (2C), 20.64, 20.57, 20.51, 20.45, 14.14.
WORKUP
后处理
- customThe resulting residue was chromatographed (SiO2 -column, 5×18 cm