A. T. Khan, S. Ghosh, L. H. Choudhury
FULL PAPER
C14H32OSi (244.49): calcd. C 68.78 H, 13.19; found C 68.91, H
13.06.
155.7 ppm. C16H26OS2Si (326.60): calcd. C 58.84, H 8.02; found C
58.72, H 8.09.
Compound 1j: White solid; m.p. 151Ϫ153 °C. IR (KBr): ν˜ ϭ 2930,
Compound 1r: Colourless liquid. IR (neat): ν˜ ϭ 3037, 2960, 2930,
2873, 1619, 1496, 1460, 1255, 1158, 1096, 846, 707 cmϪ1. 1H NMR
(400 MHz, CDCl3): δ ϭ 0.01 [s, 3 H, Si(CH3)2], 0.02 [s, 3 H,
Si(CH3)2], 0.85 [s, 9 H, SiC(CH3)3], 1.25 (t, J ϭ 7.3 Hz, 3 H,
SCH2CH3), 2.63Ϫ2.71 (m, 2 H, SCH2CH3), 3.21Ϫ3.24 (m, 1 H,
H-5), 3.46 (t, J ϭ 9.0 Hz, 1 H, H-3), 3.56 (t, J ϭ 9.3 Hz, 1 H, H-
2), 3.61 (t, J ϭ 9.0 Hz, 1 H, H-4), 3.75 (dd, J ϭ 3.8, J ϭ 11.2 Hz,
1 H, H-6), 3.80 (dd, J ϭ 2.0, J ϭ 11.7 Hz, 1 H, H-6Ј), 4.38 (d, J ϭ
9.8 Hz, 1 H, H-1), 4.62 (d, J ϭ 10.2 Hz, 1 H, OCHPh), 4.68 (d,
J ϭ 10.2 Hz, 1 H, OCHPh), 4.79 (dd, J ϭ 4.6, J ϭ 10.7 Hz, 2 H,
OCH2Ph), 4.85 (dd, J ϭ 4.0, J ϭ 10.3 Hz, 2 H, OCH2Ph),
7.19Ϫ7.33 (m, 15 H, ArH) ppm. 13C NMR (100 MHz, CDCl3):
δ ϭ Ϫ5.4, Ϫ5.0, 15.2, 18.3, 24.3, 25.9, 62.3, 75.1, 75.5, 75.9, 77.7,
80.0, 81.8, 84.4, 86.6, 127.7, 127.8, 127.9, 128.0, 128.3, 128.4, 128.5,
138.2, 138.3, 138.5 ppm. C35H48O5SSi (608.91): calcd. C 69.04, H
7.95, S 5.27; found C 69.22, H 7.87, S 5.12.
2858, 1665, 1460, 1378, 1255, 1112 cmϪ1 1H NMR (400 MHz,
.
CDCl3): δ ϭ 0.06 (s, 3 H, SiCH3), 0.12 (s, 3 H, SiCH3), 0.82 (s, 6
H, 2 ϫ CH3), 0.83 [s, 9 H, SiC(CH3)3], 0.85 (d, J ϭ 6.3 Hz, 3 H,
CHCH3), 0.94 (s, 6 H, 2 ϫ CH3), 1.00Ϫ1.50 (m, 22 H, CH and
CH2), 1.75 (m, 2 H, CH2), 1.94 (m, 2 H, CH2), 2.12 (m, 1 H, CH),
2.20 (m, 1 H, CH), 3.42 (q, J ϭ 6.0 Hz, 1 H, OCH), 5.25 (m, 1
H, ϭCH) ppm. C33H60OSi (500.92): calcd. C 79.13, H 12.07; found
C 79.09, H 12.11.
Compound 1k: Colourless liquid. IR (neat): ν˜ ϭ 2955, 2930, 2858,
1665, 1465, 1383, 1255, 1096, 1061, 835 cmϪ1. 1H NMR (400 MHz,
CDCl3): δ ϭ 0.01 [s, 6 H, Si(CH3)2], 0.84 [s, 9 H, SiC(CH3)3], 1.53
[s, 6 H, C(CH3)3], 1.61 (s, 3 H, CH3), 1.88Ϫ2.03 (m, 4 H, CHCH2),
3.54Ϫ3.59 (m, 1 H, OCH2), 4.12Ϫ4.13 (m, 1 H, OCH2), 5.01Ϫ5.05
(m, 1 H, CH), 5.22Ϫ5.25 (m, 1 H, CH) ppm. C16H32OSi (268.51):
calcd. C 71.57, H 12.01; found C 71.75, H 12.09.
Compound 1s: Colourless liquid. IR (neat): ν˜ ϭ 2929, 2858, 1603,
Compound 1l: Yellowish liquid. IR (neat): ν˜ ϭ 2955, 2934, 2863,
1459, 1362, 1260, 1106, 1060, 845, 742, 701 cmϪ1 1H NMR
.
1465, 1357, 1255, 1137, 1070, 840 cmϪ1 1H NMR (400 MHz,
.
(300 MHz, CDCl3): δ ϭ Ϫ0.12 (s, 3 H, SiCH3), Ϫ0.05 (s, 3 H,
SiCH3), 0.83 [s, 9 H, Si (CH3)3], 1.86 (t, J ϭ 10.8 Hz, 1 H, H-4),
3.38 (s, 3 H, OCH3), 3.39Ϫ3.44 (m, 1 H, H-1), 3.53Ϫ3.66 (m, 3 H,
CH2 & H-2), 3.88 (dd, J ϭ 1.8, J ϭ 10.5 Hz, 1 H, HЈ- 6), 3.95 (d,
J ϭ 10.8 Hz, 1 H H-5), 4.06 (t, J ϭ 9.9 Hz, 1 H, H-3), 4.43 (d, J ϭ
12.3 Hz, 1 H, OCH2), 4.61 (m, 3 H, OCH2 & H-6), 4.65 (d, J ϭ
12.6 Hz, 1 H, OCH2), 4.77 (d, J ϭ 12.0 Hz, 1 H, OCH2), 5.01 (d,
J ϭ 12.0 Hz, 1 H, OCH2), 7.26Ϫ7.37 (m, 15 H, ArH) ppm. 13C
NMR (75 MHz, CDCl3): δ ϭ Ϫ5.8, Ϫ5.5, 18.1, 25.8, 44.8, 55.0,
58.3, 68.3, 69.3, 73.0, 73.4, 75.3, 75.7, 81.7, 98.5, 127.6, 127.7,
127.8, 127.9, 128.2, 128.4, 138.2, 138.4, 139.1 ppm. C35H48O6Si
(592.84): calcd. C 70.91, H 8.16; found C 70.68, H 8.24.
CDCl3): δ ϭ 0.12 [s, 12 H, 2 ϫ Si (CH3)2], 0.91 [s, 18 H, 2 ϫ SiC
(CH3)3], 4.34 (s, 4 H, OCH2) ppm. C16H34O2Si2 (314.61): calcd. C
61.08, H 10.89; found C 61.10, H 10.85.
Compound 1m: Colourless liquid. IR (neat): ν˜ ϭ 2945, 2863, 1460,
1378, 1255, 1148, 1107, 846, 784 cmϪ1. C10H26O3Si (222.40): calcd.
C 54.01, H 11.78; found C 54.12, H 11. 83.
Compound 1n: Colourless liquid. IR (neat): ν˜ ϭ 3058, 2966, 2940,
2863, 1634, 1603, 1506, 1470, 1363, 1260, 1230, 1173, 1132, 1015,
933, 851 cmϪ1 1H NMR (300 MHz, CDCl3): δ ϭ 0.25 [s, 6 H,
.
Si(CH3)2], 1.02 [s, 9 H, SiC(CH3)3], 7.07 (dd, J ϭ 3.2, J ϭ 8.7 Hz,
1 H, 3-ArH), 7.19 (d, J ϭ 2.4 Hz, 1 H, 1-ArH), 7.30 (t, J ϭ 7.0 Hz,
1 H, 6-ArH), 7.38 (t, J ϭ 7.0 Hz, 1 H, 7-ArH), 7.68 (d, J ϭ 8.7 Hz,
1 H, ArH, 4-ArH), 7.72 (d, J ϭ 9.0 Hz, 1 H, 5-ArH), 7.76 (d, J ϭ
8.1 Hz, 1 H, 8-ArH) ppm. 13C NMR (75 MHz, CDCl3): δ ϭ Ϫ4.3,
18.3, 25.7, 114.9, 122.1, 123.7, 126.1, 126.7, 127.6, 129.3, 134.6,
153.5 ppm. C16H22OSi (258.43): calcd. C 74.36, H 8.58; found C
74.10, H 8.50.
Compound 1t: Yellowish liquid. IR (neat): ν˜ ϭ 2986, 2935, 2858,
1475, 1378, 1312, 1255, 1214, 1112, 1071, 1004, 840 cmϪ1 1H NMR
(300 MHz, CDCl3): δ ϭ 0.07 [s, 6 H, Si(CH3)2], 0.90 [s, 9 H,
SiC(CH3)3], 1.33 (s, 6 H, 2 ϫ CH3), 1.44 (s, 3 H, CH3), 1.54 (s, 3
H, CH3), 3.70Ϫ3.86 (m, 3 H, H-2, H-3, H-5), 4.30 (dd, J ϭ 2.3,
J ϭ 7.2 Hz, 2 H, H-4, H-6), 4.60 (dd, J ϭ 1.6, J ϭ 7.9 Hz, 1 H,
H-6Ј), 5.52 (d, J ϭ 4.9 Hz, 1 H, H-1) ppm. C18H34O6Si (374.55):
calcd. C 57.72, H 9.15; found C 57.89, H 9.02.
Compound 1o: Yellowish liquid. IR (neat): ν˜ ϭ 2945, 2858, 1705,
1603, 1511, 1270, 1157, 912, 845 cmϪ1 1H NMR (300 MHz,
.
Compound 1u: White solid; m.p. 115 °C. IR (KBr): ν˜ ϭ 3180, 3057,
2950, 2929, 2858, 1700, 1465, 1362, 1270, 1101, 1065, 1029, 835,
778 cmϪ1.1H NMR (300 MHz, CDCl3): δ ϭ 0.06 (s, 3 H, SiCH3),
0.07 (s, 3 H, SiCH3), 0.10 (s, 6 H, SiCH3), 0.88 [s, 9 H, SiC(CH3)3],
0.91 [s, 9 H, SiC(CH3)3], 1.91 (s, 3 H, CH3) 1.94Ϫ2.03 (m, 1 H, H-
2), 2.21Ϫ2.28 (m, 1 H, HЈ-2), 3.75 (dd, J ϭ 2.3, J ϭ 13.7 Hz, 1 H,
H-4), 3.84Ϫ3.92 (m, 2 H, OCH2), 4.37Ϫ4.41 (m, 1 H, H-3),
6.30Ϫ6.35 (m, 1 H, H-1), 7.46 (s, 1 H, CH), 9.01 (s, 1 H, NH) ppm.
C22H42N2O5Si2 (470.75): calcd. C 56.13, H 8.99, N 5.95; found C
56.34, H 8.89, N 6.12.
CDCl3): δ ϭ 0.25 [s, 6 H, Si(CH3)2], 0.99 [s, 9 H, SiC(CH3)3], 6.95
(d, J ϭ 8.4 Hz, 2 H, ArH), 7.81 (d, J ϭ 8.4 Hz, 2 H, ArH), 9.89
(s, 1 H, CHO) ppm. C13H20O2Si (236.39): calcd. C 66.06, H 8.53;
found C 65.37, H 8.58.
Compound 1p: Colourless liquid. IR (neat): ν˜ ϭ 2966, 2935, 2863,
1711, 1593, 1470, 1255, 1107, 974, 840 cmϪ1. 1H NMR (300 MHz,
CDCl3): δ ϭ 0.19 [s, 6 H, Si(CH3)2], 0.94 [s, 9 H, SiC(CH3)3], 2.47
(s, 3 H, COCH3), 3.77 (s, 3 H, OCH3), 6.37 (d, J ϭ 8.3 Hz, 1 H,
ArH), 6.51 (d, J ϭ 8.3 Hz, 1 H, ArH), 7.15 (t, J ϭ 8.3 Hz, 1 H,
ArH) ppm. C15H24O3Si (280.44): calcd. C 64.24, H 8.63; found C
64.45, H 8.58.
Compound 1v: White solid; m.p. 145 °C. IR (KBr): ν˜ ϭ 3247, 3083,
2940, 2863, 1736, 1700, 1467, 1372, 1255, 1203, 1121, 1014, 835
Compound 1q: White solid; m.p. 82.6 °C. IR (neat): ν˜ ϭ 2955, 2929, cmϪ1.1H NMR (300 MHz, CDCl3): δ ϭ 0.14 (s, 6 H, Si (CH3) ),
2
2893, 2852, 1608, 1511, 1470, 1419, 1255, 1168, 912, 845 cmϪ1. 1H
NMR (300 MHz, CDCl3): δ ϭ 0.09 [s, 6 H, Si (CH3)2], 0.97 [s, 9 2.12 (m, 2 H, H-2, H-2Ј), 2.41 (dd, J ϭ 5.2, J ϭ 13.7 Hz, 1 H),
H, SiC(CH3)3], 1.84Ϫ1.88 (m, 1 H, SCH2CH2), 1.91Ϫ1.97 (m, 1 3.92 (d, J ϭ 1.8 Hz, 2 H, CH2OTBS), 4.10 (d, J ϭ 1.1 Hz, 1 H,
H, SCH2CH2), 2.85Ϫ2.92 (m, 2 H, SCH2CH2), 2.99Ϫ3.09 (m, 2 5.25 (d, J ϭ 5.9 Hz, 1 H), 6.38 (dd, J ϭ 5.2, J ϭ 9.2 Hz, 1 H), 7.55
H, SCH2CH2), 5.12 (s, 1 H, CH), 6.79 (d, J ϭ 8.4 Hz, 2 H, ArH), (d, J ϭ 1.1 Hz, 1 H, ArH), 9.12 (s, 1 H, NH) ppm. C18H30N2O6Si
7.32 (d, J ϭ 8.4 Hz, 2 H, ArH) ppm. 13C NMR (75 MHz, CDCl3): (398.53): calcd. C 54.25, H 7.59, N 7.03; found C 54.16, H 7.49,
δ ϭ Ϫ4.5, 18.1, 25.0, 25.6, 32.1, 50.8, 120.1, 128.8, 131.8, N 7.11.
0.93 [s, 9 H, SiC(CH3)3], 1.93 (s, 3 H, CH3), 2.11 (s, 3 H, COCH3),
2202
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Org. Chem. 2004, 2198Ϫ2204