Int. J. Mol. Sci. 2021, 22, 5626
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2
.73 (1H, d, J = 4.9 Hz), 3.87 (1H, d, J = 2.1 Hz), 4.39 (1H, d, J = 11.8 Hz), 4.62 (1H, d,
13
J = 11.8 Hz), 7.25–7.33 (5H, m). C NMR (125 MHz, CDCl3):
7.7, 47.2, 53.6, 58.5, 70.3, 74.9, 127.4, 127.5, 128.4, 139.4. Found: C, 78.47; H 9.33. Anal.
Calcd for C H O : C, 78.42; H, 9.29.
δ = 20.8, 22.1, 22.4, 26.4, 34.6,
3
17
24
2
(S)-2-((1R,2S,4R)-2-(Benzyloxy)-4-methylcyclohexyl)-2-methyloxirane (4b)
2
0
Prepared with
c 0.385, MeOH). H NMR (500 MHz, CDCl ):
3
eluted by n-hexane:EtOAc = 9:1. Yield: 47%, colorless oil. [α] = +88.7
D
1
(
δ
= 0.87 (3H, d, J = 6.4 Hz), 0.84–0.95 (2H, m),
3
1
.19–1.24 (1H, m), 1.33 (3H, s), 1.62–1.66 (1H, m), 1.77–1.82 (3H, m), 2.02–2.07 (1H, m), 2.49
(
1H, d, J = 4.9 Hz), 2.68 (1H, d, J = 4.9 Hz), 2.72 (1H, d, J = 2.2 Hz), 4.35 (1H, d, J = 11.7 Hz),
4
2
9
.60 (1H, d, J = 11.7 Hz), 7.25–7.34 (5H, m). 13C NMR (125 MHz, CDCl3):
6.3, 34.8, 37.6, 53.4, 59.4, 70.1, 75.6, 76.9, 77.1, 127.4, 127.6, 128.4, 139.2. Found: C, 78.40; H
.25. Anal. Calcd for C H O : C, 78.42; H, 9.29.
δ = 20.5, 22.4, 23.2,
17
24
2
(S)-2-((1R,2S,4R)-2-(Benzyloxy)-4-methylcyclohexyl)-2-((benzyloxy)methyl)oxirane (19a)
2
0
Prepared with 18a eluted by n-hexane:EtOAc = 9:1. Yield: 36%, colorless oil. [α] = +47.0
D
1
(
c 0.25, MeOH). H NMR (500 MHz, CDCl ):
δ
= 0.87 (3H, d, J = 6.4 Hz), 0.86–0.97 (2H,
3
m), 1.40–1.50 (2H, m), 1.69–1.75 (2H, m), 1.89–1.93 (1H, m), 2.04–2.09 (1H, m), 2.64 (1H, d,
J = 4.7 Hz), 2.80 (1H, d, J = 4.8 Hz), 2.87 (1H, d, J = 11.6 Hz), 3.73 (1H, d, J = 11.6 Hz), 3.83 (1H,
d, J = 5.4 Hz), 4.25 (1H, d, J = 11.8 Hz), 4.40 (1H, d, J = 12.1 Hz), 4.51 (1H, d, J = 12.0 Hz), 4.57
(
3
1H, d, J = 11.9 Hz), 7.24–7.34 (10H, m). 13C NMR (125 MHz, CDCl3):
δ
= 21.1, 22.4, 26.4, 34.5,
7.3, 42.4, 48.3, 60.1, 70.1, 71.6, 73.2, 74.3, 127.4, 127.5, 127.7, 127.8, 128.4, 128.5. Found: C, 78.67;
H 8.23. Anal. Calcd for C H O : C, 78.65; H, 8.25.
24
30
3
(R)-2-((1R,2S,4R)-2-(Benzyloxy)-4-methylcyclohexyl)-2-((benzyloxy)methyl)oxirane (19b)
2
0
Prepared with 18a eluted by n-hexane:EtOAc = 9:1. Yield: 36%, colorless oil. [α] = +54.0
D
1
(
c 0.25, MeOH). H NMR (500 MHz, CDCl ):
δ
= 0.86 (3H, d, J = 6.5 Hz), 0.85–0.95 (4H, m),
3
1.26–1.29 (2H, m), 1.50 (2H, m), 1.62–1.76 (5H, m), 2.01–2.04 (1H, m), 2.69 (1H, d, J = 5.3 Hz),
2
.84 (1H, d, J = 5.4 Hz), 3.58 (1H, d, J = 10.9 Hz), 3.70 (1H, d, J = 11.4 Hz), 3.76 (1H, s) 4.32 (1H,
13
d, J = 11.6 Hz), 4.48 (2H, s), 4.54 (1H, d, J = 11.6 Hz), 7.23–7.32 (10H, m). C NMR (125 MHz,
CDCl3): = 22.4, 23.1, 26.3, 34.9, 37.7, 43.9, 48.9, 60.8, 70.2, 71.3, 73.5, 74.8, 127.4, 127.7, 127.8,
28.4, 128.4, 128.5, 138.6, 139.3. Found: C, 78.62; H 8.23. Anal. Calcd for C H O : C, 78.65;
δ
1
24
30
3
H, 8.25.
(
1R,2R,5R)-2-((S)-2-((Benzyloxy)methyl)oxiran-2-yl)-5-methylcyclohexanol (24a)
2
0
Prepared with 18b eluted by n-hexane:EtOAc = 4:1. Yield: 42%, colorless oil. [α] = +37.0
D
1
(
c 0.275, MeOH). H NMR (500 MHz, CDCl ):
δ
= 0.86 (3H, d, J = 6.4 Hz), 0.88–0.96 (1H, m),
3
1
2
.00–1.06 (1H, m), 1.45–1.49 (1H, m), 1.55–1.59 (2H, m), 1.66–1.1.78 (2H, m), 1.82–1.87 (2H, m),
.67 (1H, d, J = 4.6 Hz), 2.80 (1H, d, J = 4.6 Hz), 3.22 (1H, d, J = 10.3 Hz), 3.37 (1H, s), 3.82 (1H,
d, J = 10.3 Hz), 4.18 (1H, s), 4.53 (1H, d, J = 11.6 Hz), 4.57 (1H, d, J = 11.8 Hz), 7.25–7.37 (5H,
13
m). C NMR (125 MHz, CDCl3):
δ = 22.2, 22.3, 25.6, 34.7, 41.7, 44.0, 50.2, 60.6, 67.8, 72.1, 73.7,
1
27.9, 128.0, 128.5, 137.1. Found: C, 78.90; H 8.77. Anal. Calcd for C H O : C, 73.88; H, 8.75.
17
24
3
(
1R,2R,5R)-2-((R)-2-((Benzyloxy)methyl)oxiran-2-yl)-5-methylcyclohexanol (24b)
2
0
Prepared with 18b eluted by n-hexane:EtOAc = 4:1. Yield: 15%, colorless oil. [α] = +24.0
D
1
(
c 0.295, MeOH). H NMR (500 MHz, CDCl ):
δ
= 0.86 (3H, d, J = 6.4 Hz), 0.88–0.95 (1H,
3
m), 1.02–1.07 (1H, m), 1.47–1.50 (1H, m), 1.57 (1H, s), 1.59–1.66 (2H, m), 1.74–1.77 (1H, m),
.82–1.88 (2H, m), 2.69 (1H, d, J = 4.6 Hz), 2.85 (1H, d, J = 4.6 Hz), 3.24 (1H, s), 3.43 (1H,
d, J = 10.8 Hz), 3.69 (1H, d, J = 10.9 Hz), 4.14 (1H, s), 4.53 (1H, d, J = 11.8 Hz), 4.61 (1H, d,
J = 11.9 Hz), 7.25–7.35 (5H, m). 13C NMR (125 MHz, CDCl3):
= 21.9, 22.3, 25.9, 34.9, 41.8,
4.3, 50.7, 66.7, 72.2, 73.8, 128.0, 128.1, 128.7, 137.4. Found: C, 78.85; H 8.74. Anal. Calcd for
C H O : C, 73.88; H, 8.75.
1
δ
4
17
24
3