L. Zhu et al.
Bioorganic Chemistry 111 (2021) 104828
1H), 4.35 (s, 1H), 3.85 (s, 1H), 3.74–3.55 (m, 1H), 3.16–2.89 (m, 5H),
2.73–2.43 (m, 5H), 1.17–1.01 (m, 6H). 13C NMR (101 MHz, CDCl3) δ
170.20, 149.26, 146.79, 129.57, 123.98, 53.70, 49.34, 34.76, 31.03,
15.99. Purity (HPLC): 95.18%. HRMS (ESI-TOF, m/z): calcd for
4.46 (brs, 2H), 4.36–3.95 (m, 4H), 3.03 (s, 1H), 2.53 (s, 1H), 1.44–1.05
(m, 12H). 13C NMR (101 MHz, CDCl3) δ 169.40, 133.93, 128.13, 128.01,
126.46, 63.13, 62.25, 49.91, 43.67, 15.33, 14.84. Purity (HPLC): 100%.
HRMS (ESI-TOF, m/z): calcd for C26H30N2NaO4 (M + Na)+ 457.2098,
found 457.2108.
C
24H28N4NaO6 (M + Na)+ 491.1901, found 491.1912.
4.3.13. ((2S,5S)-2,5-dimethylpiperazine-1,4-diyl) bis(((2S,3R)-3-(4-
nitrophenyl) oxiran-2-yl) methanone) (b-7)
4.3.19. ((2R,5R)-2,5-dimethylpiperazine-1,4-diyl) bis(((2R,3S)-2-methyl-
3-phenyloxiran-2-yl) methanone) (c-3)
25.2
Creamy white color solid, the yield of the compound: 80%. decom-
Colorless oil, the yield of the compound: 85%. [
α
]
D
–109.52 (c:
24.1
poseed ~ 235 ◦C. [
α]
+ 200.000 (c: 0.410, chloroform). 1H NMR
0.630, chloroform). 1H NMR (400 MHz, CDCl3) δ 7.42–7.27 (m, 10H),
4.46 (brs, 2H), 4.37–4.11 (m, 4H), 3.31–3.07 (m, 2H), 1.31 (s, 6H), 1.22
(d, J = 4.7 Hz, 6H). 13C NMR (101 MHz, CDCl3) δ 169.67, 133.92,
128.49, 128.39, 126.60, 63.16, 62.62, 49.72, 44.03, 16.04, 14.90. Pu-
rity (HPLC): 95.79%. HRMS (ESI-TOF, m/z): calcd for C26H30N2NaO4
(M + Na)+ 457.2098, found 457.2114.
D
(400 MHz, CDCl3) δ 8.28–8.11 (m, 4H), 7.57–7.42 (m, 4H), 4.72–4.60
(m, 1H), 4.58–4.45 (m, 1H), 4.39–4.27 (m, 1H), 4.27–4.15 (m, 2H),
4.11–3.94 (m, 1H), 3.59 (s, 2H), 3.29–2.99 (m, 1H), 2.85–2.64 (m, 1H),
1.19 (d, J = 6.0 Hz, 6H). 13C NMR (101 MHz, CDCl3) δ 165.38, 148.50,
142.83, 126.79, 124.30, 57.32, 50.07, 44.05, 41.15, 18.93, 15.86. Pu-
rity (HPLC): 95.78%. HRMS (ESI-TOF, m/z): calcd for C24H24N4NaO8
(M + Na)+ 519.1486, found 519.1481.
4.3.20. ((2S,5S)-2,5-dimethylpiperazine-1,4-diyl) bis(((2R,3S)-2-methyl-
3-phenyloxiran-2-yl) methanone) (c-4)
25.0
4.3.14. ((2R,5R)-2,5-dimethylpiperazine-1,4-diyl) bis(((2S,3R)-3-(4-
nitrophenyl) oxiran-2-yl) methanone) (b-8)
Colorless oil, the yield of the compound: 86%. [
α]
+ 61.053 (c:
D
2.850, chloroform). 1H NMR (400 MHz, CDCl3) δ 7.40–7.27 (m, 10H),
4.45 (brs, 2H), 4.34–3.93 (m, 4H), 3.05 (s, 1H), 2.53 (s, 1H), 1.48–1.06
(m, 12H). 13C NMR (101 MHz, CDCl3) δ 169.61, 134.21, 128.42, 128.30,
126.74, 63.40, 62.50, 50.28, 43.90, 15.55, 15.12. Purity (HPLC): 100%.
HRMS (ESI-TOF, m/z): calcd for C26H30N2NaO4 (M + Na)+ 457.2098,
found 457.2117.
Creamy white color solid, the yield of the compound d: 79%.
decomposeed ~ 236 ◦C. [
α
]
24.2 –3.125 (c: 0.320, chloroform). 1H NMR
(400 MHz, CDCl3) δ 8.21 (d,DJ = 8.0 Hz, 4H), 7.50 (s, 4H), 4.69–4.38 (m,
2H), 4.37–3.97 (m, 4H), 3.66–3.43 (m, 2H), 3.13 (s, 1H), 2.67 (s, 1H),
1.43–1.10 (m, 6H). 13C NMR (101 MHz, CDCl3) δ 164.87, 148.23,
142.94, 126.81, 124.05, 56.94, 50.56, 49.62, 43.85, 41.27, 17.83,
15.64. Purity (HPLC): 98.19%. HRMS (ESI-TOF, m/z): calcd for
4.3.21. ((2S,5S)-2,5-dimethylpiperazine-1,4-diyl) bis(((2S,3R)-2-methyl-
3-(2-nitrophenyl) oxiran-2-yl) methanone) (c-5)
C
24H24N4NaO8 (M + Na)+ 519.1486, found 519.1479.
Creamy white color solid, the yield of the compound: 73%. m.p.:
4.3.15. ((2R,5R)-2,5-dimethylpiperazine-1,4-diyl) bis(((2R,3S)-3-(4-
nitrophenyl) oxiran-2-yl) methanone) (b-9)
70 ◦C–71 ◦C. [
α
] D24.8 + 132.961 (c: 0.895, chloroform). 1H NMR (400
MHz, CDCl3) δ 8.23–8.16 (m, 2H), 7.73–7.66 (m, 2H), 7.65–7.58 (m,
2H), 7.57–7.50 (m, 2H), 4.69 (s, 2H), 4.62–4.43 (m, 2H), 4.41–4.22 (m,
2H), 3.30–3.04 (m, 2H), 1.29–1.20 (m, 12H). 13C NMR (101 MHz,
CDCl3) δ 168.28, 147.76, 133.71, 130.77, 129.49, 129.19, 124.91,
63.62, 61.31, 49.90, 43.99, 15.91, 15.46. Purity (HPLC): 96.26%. HRMS
(ESI-TOF, m/z): calcd for C26H28N4NaO8 (M + Na)+ 547.1799, found
547.1814.
Creamy white color solid, the yield of the compound: 70%. decom-
poseed ~ 237 ◦C. [
α
]
D
24.3 + 196.67 (c: 0.300, chloroform). 1H NMR (400
MHz, CDCl3) δ 8.25–8.14 (m, 4H), 7.55–7.44 (m, 4H), 4.72–4.57 (m,
1H), 4.55–4.45 (m, 1H), 4.40–4.14 (m, 3H), 4.12–3.98 (m, 1H),
3.68–3.55 (m, 2H), 3.28–3.07 (m, 1H), 2.86–2.67 (m, 1H), 1.18 (d, J =
6.2 Hz, 6H). 13C NMR (101 MHz, CDCl3) δ 165.36, 148.44, 142.85,
126.79, 124.26, 57.30, 50.02, 44.03, 41.12, 18.91, 15.82. Purity
(HPLC): 99.12%. HRMS (ESI-TOF, m/z): calcd for C24H24N4NaO8 (M +
Na)+ 519.1486, found 519.1481.
4.3.22. ((2S,5S)-2,5-dimethylpiperazine-1,4-diyl) bis(((2S,3R)-2-methyl-
3-(3-nitrophenyl) oxiran-2-yl) methanone) (c-7)
Creamy white color solid, the yield of the compound: 78%. m.p.:
4.3.16. ((2S,5S)-2,5-dimethylpiperazine-1,4-diyl) bis(((2R,3S)-3-(4-
nitrophenyl) oxiran-2-yl) methanone) (b-10)
80 ◦C–81 ◦C. [
α
] D25.1 + 115.951 (c: 1.630, chloroform). 1H NMR (400
MHz, CDCl3) δ 8.25–8.16 (m, 4H), 7.74–7.68 (m, 2H), 7.63–7.57 (m,
2H), 4.46 (brs, 2H), 4.37–4.20 (m, 4H), 3.38–3.13 (m, 2H), 1.33 (s, 6H),
1.30–1.20 (m, 6H). 13C NMR (101 MHz, CDCl3) δ 168.75, 148.33,
136.26, 132.61, 129.53, 123.31, 121.54, 63.57, 61.69, 49.85, 43.87,
15.90, 14.92. Purity (HPLC): 96.39%. HRMS (ESI-TOF, m/z): calcd for
Creamy white color solid, the yield of the compound: 80%. decom-
24.3
poseed ~ 242 ◦C. [
α
]
–6.061 (c: 0.330, chloroform). 1H NMR (400
D
MHz, CDCl3) δ 8.28–8.10 (m, 4H), 7.56–7.40 (m, 4H), 4.70–4.37 (m,
2H), 4.36–3.95 (m, 4H), 3.67–3.41 (m, 2H), 3.12 (s, 1H), 2.67 (s, 1H),
1.44–1.07 (m, 6H). 13C NMR (101 MHz, CDCl3) δ 164.90, 148.41,
142.98, 126.85, 124.20, 56.95, 49.66, 43.86, 41.38, 17.54, 15.73. Pu-
rity (HPLC): 98.25%. HRMS (ESI-TOF, m/z): calcd for C24H24N4NaO8
(M + Na)+ 519.1486, found 519.1482.
C
26H28N4NaO8 (M + Na)+ 547.1799, found 547.1801.
4.3.23. ((2S,5S)-2,5-dimethylpiperazine-1,4-diyl) bis(((2R,3S)-2-methyl-
3-(3-nitrophenyl) oxiran-2-yl) methanone) (c-8)
Creamy white color solid, the yield of the compound: 76%. m.p.:
24.9
4.3.17. ((2S,5S)-2,5-dimethylpiperazine-1,4-diyl) bis(((2S,3R)-2-methyl-
3-phenyloxiran-2-yl) methanone) (c-1)
78 ◦C–79 ◦C. [
α
]
D
+ 121.481 (c: 1.350, chloroform). 1H NMR (400
MHz, CDCl3) δ 8.24–8.14 (m, 4H), 7.70 (d, J = 7.7 Hz, 2H), 7.56 (t, J =
7.9 Hz, 2H), 4.46 (brs, 2H), 4.37–4.04 (m, 4H), 3.07 (s, 1H), 2.55 (s, 1H),
1.44–1.10 (m, 12H). 13C NMR (101 MHz, CDCl3) δ 168.83, 148.53,
136.66, 132.98, 129.70, 123.48, 121.81, 63.91, 61.68, 50.55, 43.96,
15.58, 15.24. Purity (HPLC): 97.13%. HRMS (ESI-TOF, m/z): calcd for
Colorless oil, the yield of the compound: 84%. [
α
] D25.1 + 39.216 (c:
2.550, chloroform). 1H NMR (400 MHz, CDCl3) δ 7.42–7.27 (m, 10H),
4.46 (brs, 2H), 4.34–4.09 (m, 4H), 3.29–3.08 (m, 2H), 1.30 (s, 6H),
1.27–1.12 (m, 6H). 13C NMR (101 MHz, CDCl3) δ 169.73, 133.99,
128.55, 128.44, 126.66, 63.25, 62.71, 49.78, 44.09, 16.11, 14.97. Pu-
rity (HPLC): 100%. HRMS (ESI-TOF, m/z): calcd for C26H30N2NaO4 (M
+ Na)+ 457.2098, found 457.2106.
C
26H28N4NaO8 (M + Na)+ 547.1799, found 547.1802.
4.3.24. ((2S,5S)-2,5-dimethylpiperazine-1,4-diyl) bis(((2S,3R)-3-(4-
bromophenyl)-2-methyloxiran-2-yl) methanone) (c-9)
4.3.18. ((2R,5R)-2,5-dimethylpiperazine-1,4-diyl) bis(((2S,3R)-2-methyl-
Creamy white color solid, the yield of the compound: 90%. m.p.:
+ 122.120 (c: 0.312, chloroform). 1H NMR
24.8
3-phenyloxiran-2-yl) methanone) (c-2)
129.3 ◦C–131.5 ◦C. [
α]
D
25.3
Colorless oil, the yield of the compound: 85%. [
α]
–163.49 (c:
(400 MHz, CDCl3) δ 7.50 (d, J = 8.2 Hz, 4H), 7.19 (d, J = 8.2 Hz, 4H),
4.42 (s, 2H), 4.26–4.16 (m, 2H), 4.14 (s, 2H), 3.25–3.10 (m, 2H), 1.28 (s,
D
0.630, chloroform). 1H NMR (400 MHz, CDCl3) δ 7.42–7.27 (m, 10H),
14