532
M. Martinková et al./Chemical Papers 65 (4) 527–535 (2011)
Table 2. Spectral data of the newly prepared compounds
Compound
Spectral data
1H NMR (400 MHz, CDCl3), δ: 1.58–1.68 (m, 1H, H2ꢀ ), 1.79 (dtd, 1H, J2 ,1
ꢀ = 2.4 Hz, J3ꢀ,2ꢀ = 7.3 Hz, J3ꢀ,2ꢀ =
III
ꢀ
7.4 Hz, J2 ,2ꢀ = 9.6 Hz, H2ꢀ ), 2.09 (s, 3H, CH3), 2.48–2.64 (m, 2H, 2 × H3ꢀ ), 3.26 (s, 3H, OCH3), 4.27 (d, 1H, JH,H
= 16.1 Hz, NCH2), 4.45 (d, 1H, J5,5 = 9.2 Hz, H5), 4.70 (d, 1H, JH,H = 16.1 Hz, NCH2), 4.72 (d, 1H, J5,5 = 9.1
Hz, H5), 5.59 (dd, 1H, J2 ,1ꢀ = 2.4 Hz, J2 ,1ꢀ = 10.4 Hz, H1ꢀ ), 7.22–7.25 (m, 3H, Ph), 7.28–7.32 (m, 2H, Ph), 9.72
(t, 1H, J3 ,CHO = 0.7 Hz, CHO)
ꢀ
ꢀ
ꢀ
ꢀ
13C NMR (100 MHz, CDCl3), δ: 20.7 (CH3), 21.6 (CH2), 39.9 (CH2), 45.8 (NCH2), 52.8 (OCH3), 65.3 (CH2), 68.4
(C), 69.8 (CH), 127.6 (3 × CH), 128.4 (2 × CH), 136.3 (C), 157.8 (CO), 168.1 (COOCH3), 170.1 (COCH3), 199.9
(CHO)
V
1H NMR (400 MHz, CDCl3), δ: 0.08 (s, 6H, 2 × CH3), 0.90 (s, 9H, 3 × CH3), 1.33 (s, 3H, CH3), 1.52 (s, 3H, CH3),
3.80 (dd, 1H, J5,4 = 8.5 Hz, J5,5 = 10.3 Hz, H5), 3.94 (dd, 1H, J5,4 = 4.4 Hz, J5,5 = 10.3 Hz, H5), 4.03 (dd, 1H,
J5,4 = 4.4 Hz, J5,4 = 8.5 Hz, H4), 4.45 (d, 1H, J6,6 = 9.3 Hz, H6), 4.48 (d, 1H, J2,1 = 3.7 Hz, H2), 4.65 (d, 1H,
J6,6 = 9.3 Hz, H6), 5.85 (d, 1H, J2,1 = 3.7 Hz, H1), 6.37 (br s, 1H, NH)
13C NMR (100 MHz, CDCl3), δ: –5.8 (CH3), –5.7 (CH3), 18.1 (C), 25.8 (3 × CH3), 26.2 (CH3), 26.6 (CH3), 60.4
(CH2), 66.7 (CH2), 67.4 (C), 78.9 (CH), 85.6 (CH), 103.7 (CH), 112.8 (OCO), 159.5 (CO)
VI
1H NMR (400 MHz, CD3OD), δ: 1.32 (s, 3H, CH3), 1.46 (s, 3H, CH3), 3.70–3.77 (m, 2H, 2 × H5), 4.01 (t, 1H, J5,4
= 6.0 Hz, J5,4 = 6.0 Hz, H4), 4.34 (d, 1H, J6,6 = 9.5 Hz, H6), 4.51 (d, 1H, J2,1 = 3.7 Hz, H2), 4.61 (d, 1H, J6,6
9.5 Hz, H6), 5.84 (d, 1H, J2,1 = 3.7 Hz, H1)
=
13C NMR (100 MHz, CD3OD), δ: 26.5 (CH3), 26.9 (CH3), 60.7 (CH2), 67.4 (CH2), 68.6 (C), 81.6 (CH), 87.0 (CH),
105.5 (CH), 113.9 (OCO), 161.3 (CO)
VII
1H NMR (400 MHz, CDCl3), δ: 1.36 (s, 3H, CH3), 1.50 (s, 3H, CH3), 4.29 (br s, 1H, H4), 4.52 (d, 1H, J5,5 = 9.8
Hz, H5), 4.59 (d, 1H, J2,1 = 3.4 Hz, H2), 4.72 (d, 1H, J5,5 = 9.8 Hz, H5), 6.11 (d, 1H, J2,1 = 3.4 Hz, H1), 6.62 (br
s, 1H, NH), 9.75 (br s, 1H, CHO)
VIIIa
1H NMR (400 MHz, CDCl3), δ: 1.31 (t, 3H, J = 7.1 Hz, CH3), 1.35 (s, 3H, CH3), 1.50 (s, 3H, CH3), 4.18–4.23 (m,
2H, CH2), 4.24 (d, 1H, J7,7 = 9.7 Hz, H7), 4.55 (dd, 1H, J6,4 = 1.6 Hz, J5,4 = 4.8 Hz, H4), 4.59 (d, 1H, J2,1 = 3.7
Hz, H2), 4.70 (d, 1H, J7,7 = 9.8 Hz, H7), 5.96 (d, 1H, J2,1 = 3.7 Hz, H1), 6.20 (dd, 1H, J6,4 = 1.7 Hz, J6,5 = 15.7
Hz, H6), 6.71 (br s, 1H, NH), 6.92 (dd, 1H, J5,4 = 4.8 Hz, J6,5 = 15.7 Hz, H5)
13C NMR (100 MHz, CDCl3), δ: 14.0 (CH3), 26.2 (CH3), 26.5 (CH3), 60.9 (CH2), 65.1 (CH2), 68.6 (C), 79.0 (CH),
84.8 (CH), 103.8 (CH), 113.1 (OCO), 125.3 (CH), 138.7 (CH), 158.2 (CO), 165.8 (COOEt)
IX
X
1H NMR (400 MHz, CDCl3), δ: 1.26 (t, 3H, J = 7.1 Hz, CH3), 1.32 (s, 3H, CH3), 1.47 (s, 3H, CH3), 1.78–1.95 (m,
2H, 2 × H5), 2.46–2.62 (m, 2H, 2 × H6), 3.94 (dd, 1H, J5,4 = 2.7 Hz, J5,4 = 9.8 Hz, H4), 4.09–4.15 (m, 2H, CH2),
4.15 (d, 1H, J7,7 = 9.9 Hz, H7), 4.50 (d, 1H, J2,1 = 3.8 Hz, H2), 4.66 (d, 1H, J7,7 = 9.8 Hz, H7), 5.87 (d, 1H, J2,1
= 3.8 Hz, H1), 6.71 (br s, 1H, NH)
13C NMR (100 MHz, CDCl3), δ: 14.2 (CH3), 23.0 (CH2), 26.2 (CH3), 26.4 (CH3), 30.6 (CH2), 60.6 (CH2), 65.6
(CH2), 67.8 (C), 79.0 (CH), 85.1 (CH), 103.6 (CH), 112.6 (OCO), 159.0 (C=O), 172.9 (COOEt)
1H NMR (400 MHz, CDCl3), δ: 1.32 (s, 3H, CH3), 1.48 (s, 3H, CH3), 1.63–1.80 (m, 4H, 2 × H5, 2 × H6), 3.49 (m,
1H, OH), 3.62–3.70 (m, 2H, 2 × H7), 3.90 (dd, 1H, J5,4 = 2.7 Hz, J5,4 = 8.5 Hz, H4), 4.10 (d, 1H, J8,8 = 9.8 Hz,
H8), 4.51 (d, 1H, J2,1 = 3.8 Hz, H2), 4.63 (d, 1H, J8,8 = 9.8 Hz, H8), 5.88 (d, 1H, J2,1 = 3.8 Hz, H1), 7.39 (br s,
1H, NH)
13C NMR (100 MHz, CDCl3), δ: 24.2 (CH2), 26.2 (CH3), 26.4 (CH3), 29.3 (CH2), 61.9 (CH2), 65.8 (CH2), 67.9
(C), 80.6 (CH), 85.1 (CH), 103.6 (CH), 112.4 (OCO), 159.3 (CO)
XI
1H NMR (400 MHz, CDCl3), δ: 1.09 (s, 3H, CH3), 1.38 (s, 3H, CH3), 1.61–1.81 (m, 3H, 2 × H5, H6), 1.86–1.96
(m, 1H, H6), 3.48 (ddd, 1H, J7,6 = 5.5 Hz, J7,6 = 6.6 Hz, J7,7 = 9.4 Hz, H7), 3.54 (ddd, 1H, J7,6 = 5.3 Hz, J7,6
=
6.4 Hz, J7,7 = 9.4 Hz, H7), 3.93 (dd, 1H, J5,4 = 3.3 Hz, J5,4 = 9.5 Hz, H4), 3.96 (d, 1H, J8,8 = 10.0 Hz, H8), 4.13
(d, 1H, J2,1 = 3.9 Hz, H2), 4.16 (d, 1H, JH,H = 15.8 Hz, NCH2), 4.48 (d, 1H, JH,H = 12.0 Hz, PhCH2O), 4.52 (d,
1H, JH,H = 12.0 Hz, PhCH2O), 4.52 (d, 1H, J8,8 = 9.9 Hz, H8), 4.93 (d, 1H, JH,H = 15.8 Hz, NCH2), 5.62 (d, 1H,
J2,1 = 3.9 Hz, H1), 7.27–7.37 (m, 10H, 2 × Ph)
13C NMR (100 MHz, CDCl3) δ: 24.0 (CH2), 25.8 (CH3), 26.2 (CH3), 26.7 (CH2), 46.7 (NCH2), 64.3 (CH2), 69.5
(CH2), 70.7 (C), 72.9 (PhCH2O), 82.5 (CH), 83.2 (CH), 103.8 (CH), 111.9 (OCO), 127.6 (3 × CH), 127.7 (2 ×
CH), 128.0 (CH), 128.4 (2 × CH), 128.7 (2 × CH), 137.4 (C), 138.3 (C), 158.6 (CO)
XIIIa
XIIIb
1H NMR (600 MHz, CDCl3), δ: 1.62–1.91 (m, 4H, 2 × H5, 2 × H6), 1.95 (s, 3H, CH3), 2.00 (s, 3H, CH3), 3.42–3.53
(m, 2H, 2 × H7), 4.03 (dd, 1H, J5,4 = 2.6 Hz, J5,4 = 9.5 Hz, H4), 4.09 (d, 1H, J8,8 = 9.7 Hz, H8), 4.23 (d, 1H,
JH,H = 16.0 Hz, NCH2), 4.46–4.51 (m, 3H, PhCH2O, H8), 4.94 (d, 1H, JH,H = 16.0 Hz, NCH2), 5.04 (d, 1H, J2,1
= 4.9 Hz, H2), 6.29 (d, 1H, J2,1 = 4.9 Hz, H1), 7.26–7.38 (m, 10H, 2 × Ph)
13C NMR (150 MHz, CDCl3), δ: 20.0 (CH3), 20.8 (CH3), 26.0 (CH2), 26.5 (CH2), 46.9 (NCH2), 66.8 (CH2), 68.9
(C), 69.4 (CH2), 73.0 (PhCH2O), 73.7 (CH), 85.0 (CH), 92.7 (CH), 127.4 (2 × CH), 127.7 (2 × CH), 127.8 (CH),
128.4 (3 × CH), 128.9 (2 × CH), 136.7 (C), 138.3 (C), 158.1 (CO), 168.6 (CO), 168.8 (CO)
1H NMR (600 MHz, CDCl3), δ: 1.62–1.91 (m, 4H, 2 × H5, 2 × H6), 2.00 (s, 3H, CH3), 2.06 (s, 3H, CH3), 3.42–3.53
(m, 2H, 2 × H7), 3.91 (dd, 1H, J5,4 = 3.2 Hz, J5,4 = 9.3 Hz, H4), 4.02 (d, 1H, J8,8 = 9.7 Hz, H8), 4.37 (d, 1H, J8,8
= 9.7 Hz, H8), 4.46–4.51 (m, 2H, PhCH2O), 4.55 (d, 1H, JH,H = 16.3 Hz, NCH2), 4.85 (d, 1H, JH,H = 16.3 Hz,
NCH2) 5.28 (d, 1H, J2,1 = 2.1 Hz, H2), 5.90 (d, 1H, J2,1 = 2.1 Hz, H1), 7.26–7.38 (m, 10H, 2 × Ph)
13C NMR (150 MHz, CDCl3), δ: 20.4 (CH3), 20.9 (CH3), 25.8 (CH2), 26.4 (CH2), 46.6 (NCH2), 66.0 (CH2), 68.7
(C), 69.3 (CH2), 73.0 (PhCH2O), 79.3 (CH), 85.8 (CH), 99.3 (CH), 127.0 (2 × CH), 127.6 (CH), 127.7 (3 × CH),
128.1 (2 × CH), 128.6 (2 × CH), 136.7 (C), 137.0 (C), 158.1 (CO), 168.9 (2 × CO)