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29.4, 28.5 (CHcholest); 22.3, 20.3, 18.5 (CHc3holest). 31P
NMR (CDCl3, 81 MHz): d 35.26, 35.14, 34.90, 34.86
(4:4:1:1).
Elemental analysis: Anal. Found: C, 75.21; H, 8.42;
N, 1.93%. Calc. for (C51H68FeNO2P): C, 75.26; H, 8.42;
N, 1.72.
FAB-MS: m=z ¼ 737[Mþ]; 304[Mþ–HP(O)OC27H45];
213[Fc–CH@NH]; 107 [þCH2Ph].
Elemental analysis: Anal. Found: C, 72.94; H, 9.02;
N, 2.11%. Calc. for (C45H64NO2PFe): C, 73.25; H, 8.74;
N, 1.90.
3.2.4. Cholesteryl N-(R)-a-methylbenzylamino(ferroce-
nyl)methane phosphonite (4d)
Y ¼ 2.37 g (63%); m.p.: 100–102 °C.
1H NMR (CDCl3, 200 MHz): d 7.43-7.33 (m, ArH,
1
5H); 7.05 and 7.01 (2d, JPH ¼ 537:1 Hz, HP, 1H); 5.40
3.2.2. Cholesteryl N-furfurylamino(ferrocenyl)methane
phosphonite (4b)
and 5.37 (m, CH–Ocholest, 1H); 4.27 and 4.19 (m, CHfer,
4H); 4.14 (s, CHfer, 5H); 3.60 (2m, CH–N, 1H); 3.67 (d,
1JPH ¼ 13:7 Hz, 1H); 3.52 (m, C@CHcholest, 1H); 2.28
(m, CH2C–Ocholest, 2H); 2.03–1.11 (m, CHcholest and
CH3 33H); 1.00 (s, CH3, 3H); 0.90 (d, J ¼ 9:2 Hz, CH3,
3H); 0.87 (d, J ¼ 6:6 Hz, 2xCH3, 6H); 0.67 (s, CH3, 3H).
13C NMR (CDCl3, 50 MHz): d 149.0 (Ccholest); 141.53
Y ¼ 2.05 g (56%); oily liquid.
5
1H NMR (CDCl3, 200 MHz): d 7.43 (m, Hfur, 1H);
1
6.83 and 6.75 (2d, JPH ¼ 543:9 Hz, HP, 1H); 6.37 (m,
4
3Hfur, 1H); 6.32 (m, Hfur, 1H); 5.37 (m, CH–Ocholest
,
1H); 4.26 and 4.18 (m, CHfer, 4H); 4.10 (s, CHfer, 5H);
3.53 (m, CH@Ccholest, 1H); 2.28 (m, CH2, 2H); 2.08-1.06
(m, CHcholest, 24H); 1.01 (s, CH3, 3H); 0.91 (d, J ¼ 9:4
Hz, CH3, 3H); 0.87 (d, J ¼ 6:8 Hz, CH3, 3H); 0.68 (s,
CH3, 3H). 13C NMR (CDCl3, 50 MHz): d 149.5 (C2fur);
149.0 (Ccholest); 143.1 (C5fur); 129.8 and 129.0 (2d,
1JCP ¼ 104:6 Hz, C–P); 111.2 (C3fur); 111.0 (C4fur); 122.8
(CHcholest); 70.9 (Cfer); 69.3 (Cp); 69.0 (Cfer); 68.7 (Cfer);
67.1 (CHcholest); 47.19 (CH2); 48.2, 46.4, 42.8, 40.5, 39.5
(Ccholest); 39.9, 39.7, 32.9, 32.7, 31.8, 30.2, 25.3, 21.6,
20.9 (CHc2holest); 48.2, 46.4, 42.8, 29.6, 29.4, 28.5
(CHcholest); 22.3, 20.3, 18.5 (CHc3holest). 31P NMR
(CDCl3, 81 MHz): d 36.23, 36.05, 35.98, 35.85. (6:6:1:1).
FAB-MS: m=z ¼ 727[Mþ]; 294[Mþ–HP(O)OC27H45];
213[Fc–CH@NH]; 81 [þCH2Fur]; 65.1[Cpþ].
1
(Cipso); 129.6 (Cortho); 125.4 and 124.8 (2d, JCP ¼ 105:6
Hz, C–P); 129.2 (Cmeta); 129.0 (Cpara); 122.8 (CHcholest);
70.9 (Cfer); 69.3 (Cp); 69.0 (Cfer); 68.7 (Cfer); 67.1
(CHcholest); 49.4 (CH); 48.2, 46.4, 42.8, 40.5, 39.5
(Ccholest); 39.9, 39.7, 32.9, 32.7, 31.8, 30.2, 25.3, 21.6,
20.9 (CHc2holest); 48.2, 46.4, 42.8, 29.6, 29.4, 28.5
(CHcholest); 24.6 (CH3); 22.3, 20.3, 18.5 (CHc3holest). 31P
NMR (CDCl3, 81 MHz): d 35.72, 35.37 (1:2).
FAB-MS: m=z ¼ 751[Mþ]; 318[Mþ–HP(O)OC27H45];
213[Fc–CH@NH]; 105 [þCH(CH3)Ph]; 65.1[Cpþ].
Elemental analysis: Anal. Found: C, 73.40; H, 8.56;
N, 1.93%. Calc. for (C46H66FeNO2P): C, 73.49; H, 8.85;
N, 1.86.
Elemental analysis: Anal. Found: C, 70.66; H, 8.40;
N, 1.75%. Calc. for (C43H62NO3PFe): C, 70.96; H, 8.59;
N, 1.92.
3.2.5. O,O0-iso-propylideneadenosinyl N-benzylamino-
(ferrocenyl)methane phosphonite (5a)
Y ¼ 0.82 g (25%); m.p.: 66–69 °C.
1H NMR (CDCl3, 200 MHz): d 8.34 (s, AdenH2, 1H);
8.15 (s, AdenH8, 1H); 7.35 (m, PhH, NH2, 7H); 7.13 and
6.98 (2d, 1JPH ¼ 550:3 Hz, HP, 1H); 6.12 (m, H1ryb, 1H);
5.33 (m, H3ryb, 1H); 4.97 (m, Hr2yb, 1H); 4.26 and 4.17 (m,
H1ryb, CHfer, 5H); 4.12 (s, CHfer, 5H); 3.56 (m, CHr2yb;, 2H);
1.54 and 1.32 (2s, CH3, 2x3H). 13C NMR (CDCl3, 50
MHz): d 154.9 (Cade); 152.0 (CHade); 147.9 (CHade); 144.8
(Cade); 141.5 (Cipso); 129.6 (Cortho); 130.4 and 129.3 (2d,
1JCP ¼ 105:6 Hz, C–P); 129.2 (Cmeta); 129.0 (Cpara); 128.4
(CHade); 85.0, 75.7, 72.8, 70.5 (CHryb); 70.9 (Cfer); 69.3
3.2.3.
nyl)methane phosphonite (4c)
Cholesteryl
N-diphenylmethylamino(ferroce-
Y ¼ 2.89 g (71%); m.p.: 65–67 °C.
1H NMR (CDCl3, 200 MHz): d 7.51-07.22 (m, ArH,
10H); 7.20 and 7.00 (2d, 1JPH ¼ 548:4 Hz, HP, 1H); 5.34
(s, CH, 1H); 4.30 and 4.26 (m, CHfer, 2H); 4.21 (s, CHfer,
5H); 4.13 (s, CH, 1H); 3.63 (m, CH@Ccholest, 1H); 2.44
(m, CH2, 2H); 2.04–1.02 (m, CHcholest, 24H); 0.99 (s,
CH3, 3H); 0.91 (d, J ¼ 9:4 Hz, CH3, 3H); 0.87 (d,
J ¼ 6:8 Hz, CH3, 3H); 0.68 (s, CH3, 3H). 13C NMR
(CDCl3, 50 MHz): d 149.0 (Ccholest); 143.5 (Cipso); 129.0
(Cp); 69.0 (Cfer); 68.7 (Cfer); 60.5 (CHr2yb); 49.1 (CH2). 31
P
NMR (CDCl3, 81 MHz): d 37.95, 37.68, 37.41 (1:2:1).
1
(Cmeta); 129.0 and 128.2 (2d, JCP ¼ 105:6 Hz, C–P);
FAB-MS: m=z ¼ 658[Mþ]; 304[Mþ–HP(O)OAden];
213[Fc–CH@NH]; 135[C5H5Nþ5 ] 91[þCH2Ph].
Elemental analysis: Anal. Found: C, 56.84; H, 5.31;
N, 12.73%. Calc. for (C31H35FeN6O5P): C, 56.55; H,
5.36; N, 12.76.
128.4 (Cortho); 127.0 (Cpara); 122.8 (CHcholest); 70.9 (Cfer);
69.3 (Cp); 69.0 (Cfer); 68.7 (Cfer); 67.1 (CHcholest); 56.4
(CH); 48.2, 46.4, 42.8, 40.5, 39.5 (Ccholest); 39.9, 39.7,
32.9, 32.7, 31.8, 30.2, 25.3, 21.6, 20.9 (CHc2holest); 48.2,
46.4, 42.8, 29.6, 29.4, 28.5 (CHcholest); 22.3, 20.3, 18.5
(CHc3holest). 31P NMR (CDCl3, 81 MHz): d 33.65, 33.58,
32.81, 32.74 (2:2:3:3).
3.2.6. O,O0-iso-propylideneadenosinyl N-furfurylamino
(ferrocenyl)methane phosphonite (5b)
FAB-MS: m=z ¼ 813[Mþ]; 380[Mþ–HP(O)OC27H45];
213[Fc–CH@NH]; 167 [þCHPh2]; 121 [CpFeþ]; 65.1
[Cpþ].
Y ¼ 2.01 g (62%); m.p.: 86–89 °C.
1H NMR (CDCl3, 200 MHz): d 8.35 (s, AdenH2, 1H);
8.17 (s, AdenH8, 1H); 7.61 (m, 5Hfur, 1H); 7.38 (s, NH2,