8497
Table 1
1H, 13C NMR and mass data of synthesized compounds
3a
3b
1H NMR (CDCl3, Me4Si) l 3.64–3.61 (t, J=6 Hz, 2H, CH2
2H, CH2CO2H), 1.63–1.51 (m, 4H, CH2CH2R), 1.29–1.24 (br s, 20H, CH2
(CD3COCD3, Me4Si) l 174.1, 61.9, 33.6, 33.2, 29.9, 29.8, 29.7, 29.6, 29.5, 29.3, 29.1, 28.9,
6
OH), 2.35–2.31 (t, J=8 Hz,
); 13C NMR
6
6
6
28.7, 26.2, 25.1
1H NMR (CDCl3, Me4Si) l 3.64–3.61 (t, J=6 Hz, 2H, CH2
6 OH), 2.35–2.31 (t, J=8 Hz,
2H, CH6 2CO2H), 1.63–1.51 (m, 4H, CH6 2CH2R), 1.29–1.26 (br s, 14H, CH6 2) [Ref. 10];
13C NMR (CD3COCD3, Me4Si) l 174.3, 62.0, 33.8, 33.3, 29.8, 29.6, 29.4, 29.2, 29.0,
28.8, 26.2, 25.2
3c
4a
1H NMR (CDCl3, Me4Si) l 3.64–3.61 (t, J=6 Hz, 2H, CH2
6
OH), 2.35–2.31 (t, J=8 Hz,
CH2R), 1.28–1.26 (br s, 10H, CH2
) [Ref. 10]; 13C
NMR (CD3COCD3, Me4Si) l 174.1, 62.0, 33.3, 33.2, 29.5, 29.4, 29.2, 28.9, 26.3, 25.1
1H NMR (CDCl3, Me4Si) l 7.26–7.20 (m, 1H, CH
ꢀCHCO2), 6.20–6.08 (m, 2H,
CH3CHꢀCHꢁ), 5.77–5.73 (d, J=15.2 Hz, 1H, CꢀCHCO2), 4.12–4.09 (t, J=6 Hz, 2H,
CO2CH2), 2.35–2.31 (t, J=8 Hz, 2H, CH2CO2H), 1.84–1.82 (d, J=5.6 Hz, 3H,
CꢀCHCH3), 1.65–1.59 (m, 4H, CH2CH2R), 1.28–1.24 (br s, 20H, CH2
); 13C NMR
2H, CH2
6
CO2H), 1.63–1.52 (m, 4H, CH2
6
6
6
6
6
6
6
6
6
6
6
(CDCl3, Me4Si) l 179.9, 167.5, 144.9, 139.1, 129.8, 119.0, 64.4, 34.4, 34.0, 29.6, 29.5, 29.4,
29.2, 29.2, 29.1, 29.0, 28.7, 28.6, 25.9, 24.6, 14.0
4b
4c
1a
1H NMR (CDCl3, Me4Si) l 7.25–7.19 (m, 1H, CH
6
ꢀCHCO2), 6.16–6.12 (m, 2H,
CH3CH
CO2CH2
1.64–1.57 (m, 4H, CH2
6
ꢀCH
), 2.34–2.30 (t, J=8 Hz, 2H, CH2
CH2R), 1.28–1.23 (br s, 14H, CH2
6
ꢁ), 5.77–5.73 (d, J=16 Hz, 1H, CꢀCH
6
CO2), 4.12–4.09 (t, J=6 Hz, 2H,
6
6
CO2H), 1.84–1.82 (d, J=6 Hz, 3H, CꢀCHCH3
6 ),
6
6
); 13C NMR (CDCl3, Me4Si) l
179.9, 167.5, 144.9, 139.2, 119.0, 64.4, 34.4, 33.9, 29.5, 29.4, 29.2, 29.0, 28.7, 28.6, 25.9,
24.7, 18.6
1H NMR (CDCl3, Me4Si) l 7.25–7.19 (m, 1H, CH
6
ꢀCHCO2), 6.20–6.08 (m, 2H,
ꢁ), 5.77–5.73 (d, J=15.6 Hz, 1H, CꢀCHCO2), 4.12–4.08 (t, J=6.8 Hz, 2H,
), 2.34–2.30 (t, J=7.4 Hz, 2H, CH2CO2H), 1.83–1.82 (d, J=6 Hz, 3H,
), 1.66–1.57 (m, 4H, CH2CH2R), 1.33–1.23 (br s, 10H, CH2
) [Ref. 5]; 13C NMR
CH3CH
CO2CH2
CꢀCHCH3
6
ꢀCH
6
6
6
6
6
6
6
(CDCl3, Me4Si) l 179.6, 167.5, 144.9, 139.2, 129.8, 119.0, 64.4, 34.1, 34.0, 29.2, 29.1, 29.0,
28.7, 25.9, 24.6, 18.6
1H NMR (CDCl3, Me4Si) l 7.25–7.18 (m, 2H, CH
6
ꢀCHCO2), 6.16–6.08 (m, 4H,
ꢁ), 5.77–5.73 (d, J=15.6 Hz, 2H, CꢀCHCO2), 5.20–5.19 (br s, 1H,
), 4.37–4.32 (br m, 4H, POCH2CH and CHCH2O2C), 4.14–4.10 (t, J=7.4 Hz,
4H, ꢀCHCO2CH2), 3.96–3.94 (br s, 2H, NCH2CH2), 3.79 (br s, 2H, NCH2CH2), 3.46 (s,
9H, NCH3), 2.29–2.23 (m, 4H, CH2CO2), 1.84–1.82 (d, J=5.6 Hz, 6H, ꢀCHCH3),
1.65–1.55 (m, 8H, CH2CH2R), 1.23 (br s, 40H, CH2
); 13C NMR (CDCl3, Me4Si) l 173.5,
CH3CH
POCH2CH
6
ꢀCH
6
6
6
6
6
6
6
6
6
6
6
6
6
173.2, 167.4, 144.8, 139.1, 129.8, 118.9, 70.2, 64.3, 62.7, 59.4, 54.6, 50.8, 34.3, 34.2, 29.7,
29.6, 29.5, 29.3, 29.2, 29.1, 28.7, 26.0, 24.9, 18.6; m/z 925 (M+H)+ (calcd: 925.6044)
1b
1c
1H NMR (CDCl3, Me4Si) l 7.22–7.18 (m, 2H, CH
6
ꢀCHCO2), 6.19–6.06 (m, 4H,
ꢁ), 5.76–5.72 (d, J=15.2 Hz, 2H, CꢀCHCO2), 5.16 (br s, 1H, POCH2CH
4.37–4.30 (m, 4H, POCH2CH and CHCH2O2C), 4.11–4.08 (t, J=6 Hz, 4H, ꢀCHCO2CH2
3.91 (br s, 2H, NCH2CH2), 3.77 (br s, 2H, NCH2CH2), 3.45 (s, 9H, NCH3), 2.29–2.23 (m,
4H, CH2CO2), 1.83–1.82 (d, J=5.6 Hz, 6H, ꢀCHCH3), 1.64–1.56 (m, 8H, CH2CH2R),
1.24–1.19 (br s, 28H, CH
2); 13C NMR (CDCl3, Me4Si) l 174.0, 173.6, 167.4, 144.9, 139.2,
CH3CH
6
ꢀCH
6
6
6 ),
6
6
6 ),
6
6
6
6
6
6
6
129.8, 119.0, 70.3, 64.4, 62.8, 58.4, 54.6, 50.7, 34.4, 34.3, 29.6, 29.5, 29.4, 29.3, 28.7, 28.6,
26.0, 25.0, 18.6; m/z 841 (M+H)+ (calcd: 841.5105)
1H NMR (CDCl3, Me4Si) l 7.24–7.17 (m, 2H, CH
6
ꢀCHCO2), 6.19–6.07 (m, 4H,
ꢁ), 5.75–5.71 (d, J=15.6 Hz, 2H, CꢀCHCO2), 5.16 (br s, 1H, POCH2CH
4.34–4.32 (br m, 4H, POCH2CH and CHCH2O2C), 4.10–4.06 (t, J=6.8 Hz, 4H,
ꢀCHCO2CH2), 3.95–3.92 (br s, 2H, NCH2CH2), 3.72 (br s, 2H, NCH2CH2), 3.43 (s, 9H,
NCH3), 2.28–2.24 (m, 4H, CH2CO2), 1.82–1.81 (d, J=5.6 Hz, 6H, ꢀCHCH3), 1.63–1.54
(m, 8H, CH2CH2R), 1.25–1.21 (br s, 20H, CH2
). [Ref. 5]; 13C NMR (CDCl3, Me4Si) l
CH3CH
6
ꢀCH
6
6
6 ),
6
6
6
6
6
6
6
6
6
6
173.5, 173.2, 167.4, 144.9, 139.3, 129.7, 118.9, 70.1, 64.3, 62.7, 59.4, 54.5, 50.5, 34.2, 34.0,
29.6, 29.3, 29.0, 28.6, 25.9, 24.8, 18.6; m/z 785 (M+H)+ (calcd: 785.4479)