Size-exclusion chromatography on Sephadex LH-20–100 (MeOH)
gave 24 (38 mg, 45%) as a colourless resin. dH (500 MHz, CD3OD)
7.32-7.28 (m, 42H, C6H5), 5.09 (s, 14H, OCH2Ph), 5.04 (s, 7H,
H-1), 4.05-4.01 (m, 7H, OCHb), 3.95 (t, J = 9.0 Hz, 7H, H-3),
3.77-3.74 (m, 21H, H-5, OCHa), 3.52 (t, J = 9.0 Hz, 7H H-4),
3.40 (dd, J = 3.2 Hz, J = 9.6 Hz, 7H, H-2), 3.21-t, J = 7.3 Hz,
14H, CH2N), 3.08 (d, J = 13.3 Hz, 7H, H-6b), 3.03-2.91 (m, 21H,
SCH2CH2N, H-6a), 2.75 (t, J = 7.4 Hz, 14H, CH2CO2), 2.64-2.57
(m, 28H, CH2SCH2CH2CO2), 1.81-1.80 (m, 14H, OCH2CH2); dC
(125 MHz, CD3OD) 173.4 (CH2C=O), 163.1 (CF3C=O), 137.6
(CH2CPh), 129.6-129.2 (Ph), 116.8 (CF3), 102.6 (C-1), 86.8 (C-4),
81.9 (C-2), 74.4 (C-3), 73.2 (C-5), 72.7 (OCH2), 67.4 (CH2Ph), 39.9
(CH2N), 36.0 (SCH2CH2CO2), 33.6 (C-6), 31.7 (SCH2CH2N), 31.3
(OCH2CH2), 29.2 (OCH2CH2CH2), 27.8 (CH2CO2).
(t, J = 7.3 Hz, SCH2CH2CH2), 1.87 (m, 14H, OCH2CH2), 1.60–
1.54(m, 14H, SCH2CH2CH2), 1.37–1.26(m, 182H, CH2 ¥13), 0.88
(t, J = 6.9 Hz, 21H, CH3); dC (125 MHz, CDCl3) 161.5 (CF3C=O),
116.0 (CF3), 101.6 (C-1), 85.6 (C-4), 80.6 (C-2), 73.2 (C-3), 72.1
(OCH2), 71.7 (C-5), 38.6 (CH2N), 32.3, 32.1, 31.6, 30.5, 29.9-29.2,
28.6, 22.8 (C-6, SCH2CH2N, OCH2CH2CH2, CH2 ¥ 15), 14.2
(CH3).
Acknowledgements
We thank the Irish Research Council for Science Engineering
and Technology (IRCSET) for a scholarship to C. Byrne, and
Enterprise Ireland for a research fellowship to F. Sallas.
References
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3770 | Org. Biomol. Chem., 2009, 7, 3763–3771
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