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ACCEPTED MANUSCRIPT
3.2.4. Isoamyl trityl ether (1d).15 Colorless oil; yield 1.24 g (75%); IR (cm-1): 3070, 3024, 2912,
1485, 1446, 1083; 1H NMR (400 MHz, CDCl3): δ 0.80 (d, 6H, J = 8.0 Hz, [m, 1H, CH(CH3)2], 1.47–
1.53 (m, 2H, CH2CH2O), 1.72-1.79 [m, 1H, CH(CH3)2], 3.06 (t, 2H, J = 8.0 Hz, CH2O), 7.25–7.36
(m, 9H, ArH), 7.49–7.51 (m, 6H, ArH); 13C NMR (100 MHz, CDCl3): δ 22.8 (2CH3), 25.2 (CH),
39.1 (CH2), 68.2 (CH2O), 86.4 (CO), 126.9 (3C), 127.8 (6C), 128.8 (6C), 144.6 (3C, ArC); MS m/z
(%): 330 (M+, 10), 244 (32), 243 (100), 253 (11), 183 (33), 165 (32), 105 (25); Anal. Calcd for
C24H26O: C, 87.23; H, 7.93. Found: C, 87.25; H, 7.90.
3.2.5. 2-Trityloxyoctane (1e).9a Colorless oil; yield 1.60 g (78%); IR (cm-1): 3055, 2925, 1598, 1489 ,
1075, 1026; 1H NMR (400 MHz, CDCl3): δ 0.83 (t, 3H, J = 8.0 Hz, CH3CH2), 0.86 (d, 3H, J = 4.0
Hz, CH3CO), 1.05–1.23 [m, 10H, (CH2)5], 3.51–3.58 (m, 1H, CHO), 7.19–7.30 (m, 9H, ArH), 7.49–
7.52 (m, 6H, ArH); 13C NMR (100 MHz, CDCl3): δ 14.2 (CH3CH2), 21.3 (CH3CO), 22.7, 25.0, 29.5,
31.9, 37.6 [(CH2)5], 70.2 (CHO), 86.5 (CO), 126.8 (3C), 127.7 (6C), 129.1 (6C), 145.7 (3C, ArC);
MS m/z (%): 372 (M+, 4), 244 (30), 243 (100), 183 (39), 165 (48), 105 (43).
3.2.6.Cyclopentyl trityl ether (1f).13 White solid; yield 0.82 g (62%); mp 84 °C; IR (cm-1): 3055,
3028, 1596, 1485, 1045; 1H NMR (300 MHz, CDCl3): δ 1.18–1.35 [m, 6H, (CH2CHH)2], 1.50–1.64
[m, 2H, (CH2CHH)2], 3.95–4.07 (m, 1H, CHO), 7.15–7.31 (m, 9H, ArH), 7.45–7.53 (m, 6H, ArH);
13C NMR (75 MHz, CDCl3): δ 23.8, 33.7 [(CH2)4], 76.5 (CHO), 86.9 (CO), 126.8 (3C), 127.8 (6C),
129.0 (6C), 145.6 (3C, ArC); MS m/z (%): 251 (M+-Ph, 6), 244 (34), 243 (100), 183 (18), 166 (6),
165 (44), 105 (17); Anal. Calcd for C24H24O: C, 87.76; H, 7.37. Found: C, 87.73; H, 7.41.
3.2.7. Cyclohexyl trityl ether (1g).9a White solid; yield 1.58 g (92%); mp 85 °C; IR (cm-1): 3000,
3010, 1600, 1450, 1000; 1H NMR (400 MHz, CDCl3): δ 1.01–1.35 [m, 6H, (CH2)3], 1.52–1.61 (m,
4H, 2CH2), 3.46 (m, 1H, CHO), 7.19–7.29 (m, 9H, ArH), 7.55–7.53 (m, 6H, ArH); 13C NMR (100
MHz, CDCl3): δ 24.4 (2C), 25.9, 33.9 (2C) [(CH2)5], 72.1 (CHO), 86.5 (CO), 126.9 (3C), 127.7 (6C),
129.1 (6C), 145.8 (3C, ArC); MS m/z (%): 342 (M+, 2), 244 (25), 243 (100), 183 (16), 165 (39), 105
(20).
3.2.8. 5-Trityloxy-2-pentanol (1h).13 White solid; yield 0.82 g (62%); mp 84 °C; IR (cm-1): 3024,
2950, 2862, 1593, 1488, 1045; 1H NMR (250 MHz, DMSO-d6): δ 0.87–1.52 [m, 8H, CH3, 2CH2, and
OH], 3.47-3.56 (m, 2H, CH2O), 3.92-3.99 (m, 1H, CHOH), 7.23–7.37 (m, 9H, ArH), 7.37–7.44 (m,
6H, ArH); 13C NMR (62.5 MHz, DMSO-d6): δ 23.1 (CH3), 33.0, 36.1 [(CH2)2], 66.2 (CH2O), 75.8
(CHOH), 86.3 (CO), 126.9 (3C), 127.8 (6C), 128.4 (6C), 145.0 (3C, ArC); MS m/z (%): 244 (M+-
C5H10O2, 35), 243 (100), 183 (20), 165 (11), 105 (28), 77 (15), 51(7); Anal. Calcd for C24H26O2: C,
83.20; H, 7.56. Found: C, 83.24; H, 7.55.
3.2.9. 1,6-Di(trityloxy)hexane (1i).13 White solid; yield 1.60 g (53%); mp 160 ºC; IR (cm-1): 3000,
3010, 2950, 1450, 1000, 1010; 1H NMR (400 MHz, MeOD-d4): δ 1.30–1.33 [m, 4H,
(CH2CH2CH2O)2], 1.53–1.62 [m, 4H, (CH2CH2CH2O)2], 3.00 [t, 4H, J = 6.6 Hz, (CH2CH2CH2O)2],
7.19–7.29 (m, 18H, ArH), 7.41–7.44 (m, 12H, ArH); 13C NMR: (100 MHz, CDCl3): δ 26.2 (2C),
30.1 (2C) [(CH2)4], 63.6 (2CH2O), 86.3 (2CO), 126.9 (6C), 127.8 (12C), 128.8 (12C), 144.6 (6C,
ArC); MS m/z (%): 259 (3), 245 (4), 244 (31), 243 (100), 241 (2), 183 (4), 165 (20), 105 (13); Anal.
Calcd for C44H42O2: C, 87.67; H, 7.02. Found: C, 87.63; H, 7.03.