JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
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3.8. Synthesis of 1-f4-benzyloxy-3-[2-benzyloxy-5-(2-tert-butylamino-1-
hydroxyethyl)-benzyloxymethyl]-phenylg-2-tert-butylamino-ethanol (8) and
its isomer (10)
A solution of compound 7 (2.0 g, 4.0 mmol) in tert-butylamine/i-PrOH (1:1, 40 ml)
was heated to reflux for 7 h. The solvent was removed under reduced pressure and
the residue was purified by flash chromatography on silica gel by using DCM/
MEOH/NH3ꢂH2O (10:1:0.1) as eluent to afford desired product solid 8 (0.94 g) as
pale yellow solid and a sticky compound 10 (0.62 g). Compound 8: 1H NMR
(500 MHz, CDCl3): d 7.46 (s, 2H), 7.40–7.24 (m, 12H), 6.88 (d, J ¼ 8.5 Hz, 2H), 5.07
(s, 4H), 4.74 (s, 4H), 4.54 (m, 2H), 2.83 (m, 2H), 2.57 (m, 2H), 1.07 (s, 18H).
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13Cf Hg NMR(125 MHz, CDCl3): d 155.6 (2C), 137.3 (2C), 135.2 (2C), 128.5 (4C),
127.7 (2C), 127.4 (2C), 127.1 (4C), 126.8 (2C), 125.9 (2C), 111.7 (2C), 72.1 (2C), 70.1
(2C), 67.77 (2C), 50.30 (2C), 50.33 (2C), 29.2 (6C). HRESIMS: m/z 641.3955
[M þ H]þ (calcd for C40H53N2O5, 641.3954).
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Compound 10: H NMR (600 MHz, CDCl3): d 7.50 (d, J ¼ 5.4 Hz, 1H), 7.39–7.25
(m, 12H), 7.13 (d, J ¼ 7.8 Hz, 1H), 6.89 (d, J ¼ 8.4 Hz, 1H), 6.85 (d, J ¼ 8.4 Hz, 1H),
5.07 (s, 2H), 5.05 (s, 2H), 4.75–4.70 (m, 4H), 4.60 (d, J ¼ 7.2 Hz, 1H), 3.81 (m, 1H),
3.50 (m, 1H), 3.26 (m, 1H), 2.85 (m, 1H), 2.61 (m, 1H), 1.10 (s, 9H), 1.01 (s, 9H).
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13Cf Hg NMR(150 MHz, CDCl3): d 155.5 (1C), 155.2 (1C), 137.2 (1C), 136.1 (1C),
136.0 (1C), 135.0 (1C), 128.5 (2C), 127.7 (1C), 127.65 (1C), 127.63 (1C), 127.33 (1C),
127.31 (1C), 127.02 (1C), 126.97 (1C), 126.93 (1C), 126.6 (1C), 126.54 (1C), 126.50
(1C), 125.86 (1C), 125.83 (1C), 111.6 (1C), 111.5 (1C), 71.9 (1C), 70.01 (1C), 69.99
(1C), 67.7 (1C), 67.6 (1C), 66.8 (1C), 58.0 (1C), 51.32 (1C), 51.30 (1C), 50.7 (1C),
50.3 (1C), 30.4 (3C), 28.9 (3C). HRESIMS: m/z 641.3956 [M þ H]þ (calcd for
C40H53N2O5, 641.3954).
3.9. Synthesis of 1,1-[oxybis[methylene(4-hydroxy-1,3-phenylene)]]bis [2-[(1,1-
dimethylethyl)amino]ethanol] (9)
A mixture of compound 8 (2.0 g, 3.1 mmol) and 10% palladium on carbon (0.1 g) in
THF (10 ml) was stirred under hydrogen at room temperature overnight. The catalyst
was filtered and washed with THF, and the combined filtrate was removed under
reduced pressure. The crude product was purified by flash chromatography on silica
gel using DCM/MeOH/NH3ꢂH2O (10:1:0.1) as eluent to afford desired product 9 as
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white solid (1.1 g, 76%). H NMR (500 MHz, DMSO-d6): d 7.25 (s, 2H), 7.05 (d,
J ¼ 7.95 Hz, 2H), 6.75 (d, J ¼ 8.2 Hz, 2H), 4.49 (s, 6H), 2.60 (d, J ¼ 8.3 Hz, 4H), 2.47
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(d, J ¼ 1.45 Hz, 2H), 1.04 (s, 18H). 13Cf Hg (125 MHz, DMSO-d6) d 153.9 (2C), 134.1
(2C), 126.4 (2C), 125.8 (2C), 124.2 (2C), 114.5 (2C), 71.4 (2C), 67.0 (2C), 51.0 (2C),
50.1 (2C), 27.9 (6C). HRESIMS: m/z 461.3015 [M þ H]þ (calcd for
C26H41N2O5, 461.3015).
Acknowledgments
The authors acknowledge Dr. PeiCheng Zhang and Qunqun Guo for useful discussion and Dr.
Yan Wu for assistance in the NMR.