F. de Souza Fernandes et al. / European Journal of Medicinal Chemistry 108 (2016) 203e210
205
0
0
0
,SR-,SS); 13C NMR (CDCl
3
.89e3.97 (m, H5 and H2 ), 3.57e3.74 (m, H6, H1 and H5 ), 3.47 (s,
3
, 75 MHz, ppm)
d
: 14.2 (CH
3
, RR-,RS-,SR-,SS),
0
0
OH), 2.53e2.51 (m, H3 , H4 and NCH
s, C(CH ), 1.25 (s, CH
aliph), 0.87 (t, J ¼ 6.8 Hz, 3H, CH
NMR (CDCl , 75 MHz, ppm) : 14.3 (CH ), 22.8, 24.6, 25.1, 26.1, 26.2,
7.0, 27.5, 29.5, 29.8, 32.1 (CH aliph and C(CH ), 55.6, 56.8, 57.1,
9.5, 67.1, 68.2, 70.6, 70.7, 70.8, 71.4, 74.1 (NCH , C3 C4 , C5 , C1 , C2 ,
).
2
), 1.53, 1.44 (s, C(CH
3
)
2
), 1.32
22.7, 24.5, 25.0, 2x25.8, 26.0, 26.1, 29.4, 29.7, 29.9, 32.0, 34.7, 34.8,
35.0 (CH aliph and C(CH , RR-,RS-,SR-,SS), 57.7, 59.3, 59.6, 60.2,
62.2, 62.3, 2x64.0, 2x67.0, 67.8, 67.9, 69.3, 69.5, 69.6, 70.6, 70.7, 71.3,
1
3
(
3
)
2
2
3
aliph);
C
2
3 2
)
3
d
3
0
00
0
0
0
0
00
2
5
2
3
)
2
73.9 (C4 , C1 , C3 , C5 , C1 , C2 , C2 , C6, C5, C4, C3, C2, RR-,RS-,SR-
,SS), 96.4 (C1, RR-,RS-,SR-,SS), 108.7, 109.4 (C(CH , RR-,RS-,SR-,SS).
0
0
0
0
0
2
3 2
)
3 2
C6, C5, C4, C3, C2), 96.5 (C1), 108.8 and 109.5 (C(CH )
2
.1.2.10. 6-O-[((R,S)-N-2-hydroxyethyl-N-(2-hydroxypropyl)amino)
tetradecan-2-ol)-N-ethanol]-1,2:3,4-di-O-isopropylidene- -gal-
/MeOH 9:1); IR (
, 300 MHz,
2
.1.2.6. 6-O-[(2,R)-N-(2-hydroxyethyl-N-dodecylamino)propan-2-
ol]-1,2:3,4-di-O-isopropylidene- -galactopyranose 10b. Oil; Yield,
4%; R : 0.55 (CH Cl /MeOH 9:1); IR (
930, 2842, 1399, 1263; H NMR (CDCl
J ¼ 4.3 Hz, H1), 4.62 (d, J ¼ 5.9 Hz, H3), 4.23e4.32 (m, H2 and H4),
a-D
a
-
D
actopyranose 14. Oil, Yield, 68%; R
cm , KBr): 3407, 2919, 2863, 1279, 1064. H NMR (CDCl
f
: 0.79 (CH
2
Cl
2
n,
ꢁ
1
ꢁ1
1
7
2
f
2
2
n
, cm , KBr): 3343, 3356,
3
1
3
, 300 MHz, ppm) : 5.54 (d,
d
ppm)
d
: 5.54 (d, J ¼ 3.5 Hz, H1, RR-,RS-,SR-,SS), 4.61 (dd, J ¼ 2.2 and
7.9 Hz, H3 RR-,RS-,SR-,SS), 4.32 (dd, J ¼ 2.2 and 4.8 Hz, H2, RR-,RS-
,SR-,SS), 4.25 (d, J ¼ 7.9 Hz, H4, RR-,RS-,SR-,SS), 3.95e3.97 (m, H5,
0 0 0
.98 (s, H5 and H2 ), 3.53e3.71 (m, H6, H1 and H5 ), 2.74e2.96 (m,
3
0
0
0 0 0 0 0
H2 and H7 , RR-,RS-,SR-,SS), 3.45e3.67 (m, H6, H1 , H5 and H3 , RR-
H3 , H4 and NCH
.24e1.25 (m, CH
aliph), 0.88 (t, J ¼ 6.8 Hz, 3H, CH
CDCl , 75 MHz, ppm) : 13.8 (CH ), 14.2, 19.9, 22.8, 24.3, 24.6, 25.0,
6.1, 26.2, 27.3, 29.5, 29.6, 29.7, 32.0 (CH aliph and C(CH ), 55.7,
7.0, 57.7, 58.9, 59.1, 67.1, 68.2, 66.9, 67.2, 70.2, 70.6, 70.8, 71.3, 73.6
2
), 1.54, 1.45 (s, C(CH
3
)
2
), 1.33 (s, C(CH
3
)
2
),
13
0
0
1
(
2
5
2
3
aliph); C NMR
,RS-,SR-,SS), 2.38e2.74 (m, H4 and H6 , RR-,RS-,SR-,SS), 1.54, 1.44 (s,
3H, C(CH , RR-,RS-,SR-,SS), 1.33 (s, C(CH , RR-,RS-,SR-,SS), 1.25 (s,
CH
aliph, RR-,RS-,SR-,SS), 0.87 (t, J ¼ 6.4 Hz, CH
NMR (CDCl , 75 MHz, ppm) : 14.2 (CH , RR-,RS-,SR-,SS), 22.8, 24.5,
25.0, 25.8, 26.1, 29.4, 29.7, 29.8, 29.9, 32.0, 34.8, 35.0, (CH aliph and
C(CH , RR-,RS-,SR-,SS), 57.6, 58.1, 58.8, 59.0, 59.3, 59.4, 59.5, 60.0,
2.1, 62.2, 3x63.9, 2x67.0, 67.4, 67.5, 67.8, 69.0, 69.2, 2x69.4, 70.2,
3
d
3
3
)
2
3 2
)
13
2
3
)
2
2
3
, RR-,RS-,SR-,SS);
C
3
d
3
0
0
0
0
0
(
NCH
2
, C3 C4 , C5 , C1 , C2 , C6, C5, C4, C3, C2), 96.5 (C1), 108.8 and
).
2
109.5 (C(CH
3
)
2
3 2
)
6
0
00
0
0
0
0
00
2
2
5
2
.1.2.7. 6-O-[(2R,S)-N-(2-hydroxyethyl-N-tetradecylamino)propan-
-ol]-1,2:3,4-di-O-isopropylidene- -galactopyranose 11. Oil, Yield,
6%; R : 0.35 (CH Cl /MeOH 9.5:0.5); IR (
823, 1380, 1080; H NMR (CDCl
70.3, 70.5, 70.6, 70.7, 71.3, 73.7, 73.8 (C4 , C1 , C3 , C5 , C1 , C2 , C2 ,
a-
D
C6, C5, C4, C3, C2, RR-,RS-,SR-,SS), 96.4 (C1, RR-,RS-,SR-,SS), 108.8,
ꢁ
1
f
2
2
n
, cm , KBr): 3343, 2930,
109.5 (C(CH
3 2
) , RR-,RS-,SR-,SS).
1
3
, 300 MHz, ppm) : 5.53 (d,
d
J ¼ 4.2 Hz, H1, R-,S-), 4.61 (d, J ¼ 7.3 Hz, H3, R-,S-), 4.24e4.32 (m, H2
2.1.2.11. 6-O-[(R,S)-N-(2-decylamino)
(ethylamino)-propan-2-ol]-
0
and H4, R-,S-), 3.94e3.97 (m, H5 and H2 , R-,S-), 3.46e3.65 (m, H6,
1,2:3,4-di-O-isopropylidene-
: 0.41 (CH Cl
1261. H NMR (CDCl
), 4.57 (d, J ¼ 7.7 Hz, H3, R-,S-), 4.21e4.28 (m, H2 and H4, R-,S-),
a-D-galactopyranose 15. Oil, Yield, 59%;
0
0
0
0
ꢁ1
H1 and H5 , R-,S-), 3.23 (s, H3 , R-,S-), 2.61e2.74 (m, H4 and NCH
R-,S-), 1.53,1.43 (s, C(CH , R-,S-), 1.33 (s, C(CH , R-,S-), 1.24 (s, CH
, R-,S-); C NMR (CDCl
, R-,S-), 22.8, 24.6, 25.0, 26.1, 26.2, 26.7,
6.8, 27.4, 29.4, 29.6, 29.7, 29.8, 32.0 (CH aliph and C(CH , R-,S-),
5.6, 56.9, 57.3, 57.4, 2x59.4, 66.8, 67.1, 67.2, 67.7, 68.0, 74.0 (NCH
2
,
R
f
2
2
/MeOH 9:1); IR (
n
, cm , KBr): 3417, 2938, 2845,
1
3
)
2
3
)
2
2
3
, 300 MHz, ppm)
d
: 5.51 (d, J ¼ 4.8 Hz, H1, R-,S-
13
aliph, R-,S-), 0.87 (t, J ¼ 6.15 Hz, CH
3
3
,
0 0 0
3.78e3.95 (m, H5 and H2 , R-,S-), 3.43e3.63 (m, H6, H1 and H3 , R-
7
2
5
5 MHz, ppm)
d
: 14.2 (CH
3
0
0
00
2
3
)
2
,S-), 2.47e2.68 (m, H1 , H2 and NCH
R-,S-), 1.30e1.23 (m, C(CH , CH aliph, R-,S-), 0.88 (t, J 6.8 Hz, CH
, 75 MHz, ppm) : 14.1 (CH
24.5, 25.0, 2x26.1, 26.2, 26.3, 26.8, 27.5, 29.2, 29.3, 29.4, 29.5, 2x29.6,
9.7, 2x31.9 (CH aliph and C(CH , R-,S-), 47.6, 50.2, 55.8, 56.3,
62.3, 66.6, 66.8, 67.0, 67.1, 68.2, 68.9, 69.0, 69.5, 69.8, 70.4, 70.6, 70.7,
2
, R-,S-), 1.51e1.42 (s, C(CH
3
)
2
,
2
,
3
)
2
2
3
,
0
0
0
0
0
13
C3 C4 , C5 , C1 , C2 , C6, C5, C4, C3, C2, R-,S-), 96.5 (C1, R-,S-), 108.8
and 109.5 (C(CH , R-,S-).
R-,S-); C NMR (CDCl
3
d
3
aliph, R-,S-), 22.7,
3 2
)
2
2
3 2
)
2
.1.2.8. 6-O-[((R,S)-N-2-hydroxyethyl-N-(2-hydroxypropyl)amino)
decan-2-ol]-1,2:3,4-di-O-isopropylidene- -galactopyranose 12.
Oil, Yield, 58%; R : 0.73 (CH Cl /MeOH 9:1); IR ( , cm , KBr): 3445,
938, 2835, 1251; H NMR (CDCl , 300 MHz, ppm) : 5.52 (d,
0
0
00
0
0
0
a-
D
71.3, 71.6, 72.6, 72.9, 73.6, 73.8 (NCH
C4, C3, C2, C1, R-,S-), 96.4 (C1, R-,S-), 108.8, 109.5 (C(CH )
2
, C2 , C1 , C3 , C1 , C2 , C6, C5,
, R-,S-).
ꢁ
1
f
2
2
n
3 2
1
2
3
d
J ¼ 4.8 Hz, H1, RR-,RS-,SR-,SS), 4.59 (d, J ¼ 5.9 Hz, H3, RR-,RS-,SR-,SS),
2.1.2.12. 6-O-[(R,S)-N-(2-dodecylamino) (ethylamino)-propan-2-ol]-
0
4
.22e4.30 (m, H2 and H4, RR-,RS-,SR-,SS), 3.95e3.96 (m, H5, H2
1,2:3,4-di-O-isopropylidene-
: 0.52 (CH Cl
1372, 1222, 1064. H NMR (CDCl
a
-
D
-galactopyranose 16. Oil, Yield, 49%;
0
0
0
0
0
ꢁ1
and H7 , RR-,RS-,SR-,SS), 3.45e3.78 (m, H6, H1 , H5 , H3 and H4 , RR-
R
f
2
2
/MeOH 9:1); IR (
n
, cm , KBr): 3407, 2919, 2845,
0
1
,
RS-,SR-,SS), 2.39e2.78 (m, H6 , RR-,RS-,SR-,SS), 1.52, 1.42 (s, C(CH
3
)
)
2
,
,
3
, 300 MHz, ppm)
d: 5.43e5.36 (m,
RR-,RS-,SR-,SS), 1.31 (s, CH
RR-,RS-,SR-,SS), 0.85 (t, J ¼ 5.7 Hz, CH
CDCl , 75 MHz, ppm) : 14.2 (CH3, RR-,RS-,SR-,SS), 22.8, 24.6, 25.0,
5.8, 26.1, 26.2, 29.4, 29.7, 29.9, 32.0, 35.0 (CH aliph and C(CH
RR-,RS-,SR-,SS), 44.5, 50.8, 50.9, 57.6, 58.0, 58.7, 58.9, 59.2, 59.3,
2
aliph, RR-,RS-,SR-,SS), 1.24 (s, C(CH
3
2
H1, NH and OH, R-,S-), 4.51 (d, J ¼ 6.1 Hz, H3, R-,S-), 4.22e4.14 (m,
13
0
H2 and H4, R-,S-), 3.87 (s, H5 and H2 , R-,S-), 3.55e3.39 (m, H6, H3
0
3
, RR-,RS-,SR-,SS); C NMR
0
00
00
(
3
d
and H1 , R-,S-), 2.97e2.47 (m, H1 , H2 and NCH
(m, C(CH and CH aliph, R-,S-), 0.78 (s, CH
(CDCl , 75 MHz, ppm) : 14.1 (CH , R-,S-), 22.6, 24.4, 24.8, 25.9, 26.0,
2X27.4, 29.2, 29.6, 31.8 (CH aliph and C(CH , R-,S-), 46.7, 51.0,
2
51.6, 55.7, 56.6, 58.9, 66.8, 70.2, 2x70.3, 70.4, 70.6, 71.1, 73.7 (NCH ,
2
, R-,S-), 1.44e1.16
3
aliph, R-,S-); C NMR
13
2
2
3
)
2
,
3
)
2
2
3
d
3
5
7
9.5, 60.1, 2x63.8, 2x66.9, 67.0, 67.2, 69.0, 69.9, 70.2, 70.3, 70.4, 70.6,
0.8, 2x71.3, 72.0, 73.9 (C4 , C1 , C3 , C5 , C1 , C2 , C2 , C6, C5, C4, C3,
2
3 2
)
0
00
0
0
0
0
00
0
0
00
0
0
0
C2, RR-,RS-,SR-,SS), 96.4, 96.5 (C1, RR-,RS-,SR-,SS), 108.7, 108.8, 109.4,
09.5 (C(CH , RR-,RS-,SR-,SS).
C2 , C1 , C3 , C1 , C2 , C6, C5, C4, C3, C2, C1, R-,S-), 96.2 (C1, R-,S-),
108.5, 109.2 (C(CH , R-,S-).
1
3
)
2
3 2
)
2
.1.2.9. 6-O-[((R,S)-N-2-hydroxyethyl-N-(2-hydroxypropyl)amino)
dodecan-2-ol]-1,2:3,4-di-O-isopropylidene- -galactopyranose 13.
Oil, Yield, 51%; R : 0.77 (CH Cl /MeOH 9:1), IR (
938, 2854, 1383, 1082. H NMR (CDCl , 300 MHz, ppm)
2.1.2.13. 6-O-[(R,S)-N-(2-tetradecylamino) (ethylamino)-propan-2-
a
-D
ol]-1,2:3,4-di-O-isopropylidene-
52%; R : 0.66 (CH Cl
2845,1251. H NMR (CDCl
R-,S-), 4.59 (d, J ¼ 8.1 Hz, H3, R-,S-), 4.22e4.30 (m, H2 and H4, R-,S-),
a
-
D
-galactopyranose 17. Oil, Yield,
ꢁ1
ꢁ1
f
2
2
n
, cm , KBr): 3360,
: 5.52 (d,
f
2
2
/MeOH 9:1). IR (
n
, cm , KBr): 3435, 2919,
1
1
2
3
d
3
, 300 MHz, ppm)
d
: 5.51 (d, J ¼ 4.8 Hz, H1,
J ¼ 3.8 Hz, H1, RR-,RS-,SR-,SS), 4.60 (d, J ¼ 7.9 Hz, H3, RR-,RS-,SR-,SS),
0 0
3.79e3.96 (m, H5 and H2 , R-,S-), 3.43e3.65 (m, H6 and H1 , R-,S-),
4
3
.31 (s, H2, RR-,RS-,SR-,SS), 4.22 (d, J ¼ 7.9 Hz, H4, RR-,RS-,SR-,SS),
0
0
0
0
0
00
00
.96 (s, H5, H2 and H7 , RR-,RS-,SR-,SS), 3.47e3.66 (m, H6, H1 , H5
2.77e2.47 (m, H3 , H1 , H2 and NCH
C(CH , CH
aliph, R-,S-), 0.86 (t, J ¼ 5.9 Hz, CH
(CDCl , 75 MHz, ppm) : 14.2 (CH , R-,S-), 22.8, 24.6, 25.1, 26.1, 26.2,
27.2, 27.6, 29.5, 29.8, 32.1 (CH aliph and C(CH , R-,S-), 47.7, 47.8,
2
, R-,S-), 1.52e1.23 (m,
0
0
0
13
and H3 , RR-,RS-,SR-,SS), 2.45e2.80 (m, H4 and H6 , RR-,RS-,SR-,SS),
.53, 1.43 (s, C(CH , RR-,RS-,SR-,SS), 1.32 (s, C(CH , RR-,RS-,SR-
SS),1.24 (s, CH , RR-,RS-
aliph, RR-,RS-,SR-,SS), 0.86 (t, J ¼ 6.8 Hz, CH
3
)
2
2
3
, R-,S-); C NMR
1
,
3
)
2
3
)
2
3
d
3
2
3
2
3 2
)