(m, 70H), 2.25 and 2.30 (overlapping t, J= 7.5 Hz each, 6H),
2.50–2.57 (m, 4H), 4.02 and 4.07 (overlapping t, J= 6.8 Hz, 8H),
4.40–4.45 (m, 1H). 13C NMR (125.75 MHz, CDCl3): 14.3, 22.9,
24.9, 25.2, 26.06, 26.11, 28.7, 28.8, 29.2, 29.3, 29.41, 29.43, 29.52,
29.57, 29.60, 29.65, 29.67, 29.68, 29.75, 29.80, 29.82, 32.1, 34.1,
34.6, 40.9, 64.6, 65.0, 65.20, 65.21, 172.1, 174.2, 179.2. HRLSIMS:
96.4, 130.0, 130.2, 174.18, 174.22, 174.3. HRLSIMS: Calcd for
+
NaC46H84O8 [M + Na+]: 787.6064 Found: 787.6042.
HO2C-Hex-Oct-Hex-Oct-G(12)-OH. Prepared using the
standard conditions on Wang resin (0.214 g, 0.16 mmol) to pro-
duce HO2C-Hex-Oct-Hex-Oct-G(12)-OH (11.3 mg; 13.3 mmol,
yield 8%). 1H NMR (500 MHz, CDCl3): 0.86 (t, J= 7.0 Hz, 3H),
1.24–1.68 (overlapping signals, 52H), 2.25–2.37 (m, 8H), 2.52–
2.53 (m, 4H), 4.01–4.11 (m, 10H), 4.40–4.46 (m, 1H). 13C NMR
(125.75 MHz, CDCl3): 14.3, 22.9, 24.1, 24.4, 24.5, 24.6, 24.7, 24.8,
25.1, 25.5, 25.5, 25.6, 25.69, 25.72, 25.75, 25.82, 25.90, 25.94, 25.97,
26.1, 28.41, 28.45, 28.55, 28.68, 28.76, 28.96, 29.07, 29.1, 29.2, 29.4,
29.6, 29.7, 29.78, 29.84, 29.85, 32.1, 33.8, 33.9, 34.4, 34.5, 40.9,
41.0, 64.2, 64.3, 64.4, 64.6, 64.7, 64.8, 65.0, 65.1, 65.3, 172.05,
172.1, 172.2, 173.8, 173.8, 173.9, 174.1, 174.2, 177.8. HRLSIMS:
Calcd for NaC53H98O11 [M + Na+]: 933.7007 Found: 933.7019.
+
HO2C-Dod-Dod-Oct-G(12)-OH. Prepared using the stan-
dard conditions, on Wang resin (0.24 g, 0.54 mmol) to produce
HO2C-Dod-Dod-Oct-G(12)-OH (27 mg;.097 mmol, yield 18%).
1H NMR (500 MHz, CDCl3): 0.85 (t, J= 7.0 Hz, 3H), 1.23–1.70
(overlapping signals, 60H), 2.261, 2.264, and 2.32 (overlapping
t, J = 7.5 Hz each, 6H), 2.51–2.58 (m, 4H), 4.03 and 4.08
(overlapping t, J = 6.7 Hz each, 8H), 4.40–4.46 (m, 1H). 13C NMR
(125.75 MHz, CDCl3): 14.3, 22.9, 24.9, 25.1, 25.2, 25.9, 26.08,
26.13, 28.68, 28.75, 28.85, 29.05, 29.18, 29.26, 29.36, 29.43, 29.45,
29.54, 29.58, 29.63, 29.66, 29.70, 29.77, 29.82, 29.84, 32.1, 34.1,
34.5, 34.6, 40.9, 64.6, 64.7, 65.0, 65.1, 65.2, 172.09, 172.11, 174.14,
Calcd for NaC45H80O13 [M + Na+]: 851.5497 Found: 851.5481.
+
HO2C-Lau-Oct-Dod-Oct-G(12)-OH. Prepared using the
standard conditions on Wang resin (0.222 g, 0.17 mmol) to
produce HO2C-Lau-Oct-Dod-Oct-G(12)-OH (6.7 mg; 6.6 mmol,
yield 4%). 1H NMR (500 MHz, CDCl3): 0.86 (t, J= 7.0 Hz,
12H), 1.12–1.71 (overlapping signals, 153H), 2.25–2.34 (m, 10H),
2.52–2.54 (m, 4H), 2.67–2.80 (m, 2H), 4.01–4.3 (overlapping
signals, 14H), 4.40–4.45 (m, 1H). 13C NMR (125.75 MHz,
CDCl3): 14.3, 22.9, 24.8, 25.0, 25.09, 25.14, 25.21, 25.76, 25.85,
25.92, 26.0, 26.10, 26.14, 26.6, 27.2, 28.5, 28.70, 28.74, 28.77,
28.81, 28.87, 28.92, 28.98, 29.05, 29.07, 29.15, 29.20, 29.24, 29.30,
29.36, 29.46, 29.57, 29.60, 29.64, 29.67, 29.71, 29.73, 29.80, 29.85,
29.86, 31.1, 32.1, 32.8, 33.7, 34.27, 34.32, 34.5, 34.6, 34.7, 40.9,
44.6, 45.2, 63.2, 64.49, 64.53, 64.62, 64.7, 65.03, 65.13, 65.3,
172.1, 172.2, 173.7, 174.2, 174.6, 176.2. HRLSIMS: Calcd for
174.3, 179.0. HRLSIMS: Calcd for NaC49H90O11 [M + Na+]:
+
877.6381 Found: 877.6384.
HO2C-Oct-Dod-Dod-G(12)-OH. Prepared using the stan-
dard conditions on Wang resin (0.305 g, 0.23 mmol) to produce
HO2C-Oct-Dod-Dod-G(12)-OH (17 mg; 0.020 mmol, yield 9%).
1H NMR (500 MHz, CDCl3): 0.85 (t, J= 6.8 Hz, 3H), 1.20–1.63
(m, 62H), 2.26 and 2.31 (overlapping t, J= 7.5 Hz each, 4H),
2.49–2.56 (m, 4H), 4.02 and 4.07 (overlapping t, J= 6.8 Hz, 8H),
4.40–4.46 (m, 1H). 13C NMR (125.75 MHz, CDCl3): 14.3, 22.9,
24.8, 24.9, 25.2, 25.9, 26.07, 26.12, 28.73, 28.78, 28.8, 29.06, 29.1,
29.21, 29.25, 29.34, 29.41, 29.44, 29.53, 29.58, 29.61, 29.66, 29.68,
29.69, 29.76, 29.81, 29.82, 32.1, 34.06, 34.13, 34.51, 34.58, 34.60,
40.9, 64.5, 64.6, 65.0, 65.21, 65.22, 172.2, 174.22, 174.3, 179.1,
+
NaC45H82O11 [M + Na+]: 1033.7531 Found: 1033.7584.
HO2C-Ole-Oct-Dod-Oct-G(12)-OH. Prepared using the stan-
dard conditions on Wang resin (0.232 g, 0.17 mmol) to produce
HO2C-Ole-Oct-Dod-Oct-G(12)-OH (13.5 mg;.015 mmol, yield
7%). 1H NMR (500 MHz, CDCl3): 0.85 (t, J= 7.0 Hz, 6H), 1.22–
1.71 (overlapping signals, 80H), 1.96–2.00 (overlapping signals,
4H), 2.25–2.34 (m, 7H), 2.52–2.54 (m, 4H), 2.6–2.8 (m, 1H), 4.01–
4.09 (overlapping signals, 8H), 4.16–4.23 (m, 2H), 4.40–4.45 (m,
1H), 5.29–5.35 (m, 1H). 13C NMR (125.75 MHz, CDCl3): 14.3,
22.9, 24.8, 25.0, 25.1, 25.2, 25.9, 25.96, 26.09, 26.14, 26.56, 27.2,
27.4, 27.4, 28.5, 28.7, 28.76, 28.80, 28.86, 28.99, 29.06, 29.08,
29.15, 29.19, 29.23, 29.29, 29.36, 29.45, 29.47, 29.53, 29.55, 29.57,
29.64, 29.71, 29.78, 29.84, 29.85, 29.98, 31.1, 32.1, 34.0, 34.29,
34.37, 34.5, 34.60 34.2, 40.9, 44.8, 45.4, 64.4, 64.5, 64.6, 64.7, 65.0,
65.1, 65.3, 129.9b, 130.3, 172.11, 172.13, 173.8, 174.16, 174.23,
174.5, HRLSIMS: Calcd for NaC64H116O13+ [M + Na+]: 1115.8314
Found: 1115.8287.
179.2. HRLSIMS: Calcd for NaC49H90O11 [M + Na+]: 877.6381
+
Found: 877.6382.
HO2C-Oct-Dod-Oct-Lau-OH. Prepared using the standard
conditions on Wang resin (0.105 g, 0.11 mmol) to produce HO2C-
1
Oct-Dod-Oct-Lau-OH (64 mg, 89.8 mmol, yield 81%). H NMR
(500 MHz, CDCl3): 0.86 (t, J= 7.0 Hz, 3H), 1.12–1.80 (overlapping
signals, 51H), 2.25–2.45 (m, 8H), 2.52–2.58 (m, 1H), 3.71–3.90 (m,
2H), 4.01–4.2 (overlapping signals, 8H). 13C NMR (125.75 MHz,
CDCl3): 13.9, 14.3, 20.0, 22.9, 24.2, 24.9, 25.0, 25.08, 25.12, 25.2,
25.8, 25.9, 26.0, 26.1, 26.6, 27.2, 27.5, 28.5, 28.75, 28.77, 28.8, 28.9,
29.0, 29.1, 29.17, 29.20, 29.24, 29.37, 29.47, 29.54, 29.65, 29.71,
29.75, 29.78, 29.80, 29.81, 29.92, 31.1, 32.1, 32.9, 33.9, 34.3, 34.5,
34.55, 34.6, 45.2, 47.8, 59.2, 63.4, 64.50, 64.53, 64.7, 64.9, 173.7,
+
174.18, 174.22, 175.86, 177.5. HRLSIMS: Calcd for NaC41H76O9
[M + Na+]: 735.5387 Found: 735.5374.
HO2C-Oct-Dod-Oct-Oleate. Prepared using the standard
conditions, on Wang resin (0.105 g, 1.1 mmol) to produce
HO2C-Oct-Dod-Oct-Oleate (2 mg, 3 mmol, yield 0.2%). 1H NMR
(500 MHz, CDCl3): 0.86 (t, J= 7.0 Hz, 3H), 1.12–1.80 (overlap-
ping signals, 66H), 1.99 (q, 3H), 2.25–2.35 (overlapping signals,
8H), 4.02–4.05 (overlapping signals, 6H), 5.31--5.33 (overlapping
signals, 2H). 13C NMR (125.75 MHz, CDCl3): 14.3, 22.9, 24.8,
25.1, 25.2, 26.0, 26.1, 26.6, 27.4, 27.5, 28.8, 28.9, 29.08, 29.12,
29.24, 29.34, 29.37, 29.40, 29.46, 29.47, 29.55, 29.65, 29.71, 29.74,
29.92, 30.0, 31.1, 32.1, 33.7, 34.55, 34.61, 64.49, 64.54, 64.7, 64.9,
Acknowledgements
The ongoing support of the Natural Sciences and Engineering
Research Council of Canada and the University of Victoria is
gratefully acknowledged.
References
1 T. M. Fyles, Chem. Soc. Rev., 2007, 36, 335–347.
2 G. W. Gokel and I. A. Carasel, Chem. Soc. Rev., 2007, 36, 378–389.
This journal is
The Royal Society of Chemistry 2009
Org. Biomol. Chem., 2009, 7, 725–732 | 731
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