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New Robust 1,2-Diol Protective Group
901
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5b: Colourless liquid. H NMR (CDCl3): ꢀ 7.90 (d, 2H, J ¼ 8.1 Hz),
7.70–7.45 (m, 3H), 5.30 (t, 1H, J ¼ 4.6 Hz), 4.55 (t, 1H, J ¼ 2.3 Hz),
3.95–3.70 (m, 7H), 3.40 (d, 2H, J ¼ 4.6 Hz), 1.65–1.15 (m, 22H); IR
(neat): 1079, 1132, 125, 1308, 1438, 2926 cmꢀ1. MS (Mþ): 454.
6b: Colourless viscous liquid. 1H NMR (CDCl3): ꢀ 7.95 (d, 2H,
J ¼ 7.5 Hz), 7.70–7.50 (m, 3H), 7.30–7.17 (m, 2H), 6.9–6.8 (m, 2H),
5.30 (t, 1H, J ¼ 5.0 Hz), 4.40 (s, 2H), 4.10–3.80 (m, 5H), 3.80 (s, 3H),
3.40 (d, 2H, J ¼ 5.0 Hz), 1.65–1.15 (m, 16H); IR (neat): 1085, 1150, 1252,
1312, 1448, 2922 cmꢀ1. MS (Mþ): 490.
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7b: Colourless liquid. H NMR (CDCl3): ꢀ 7.95 (d, 2H, J ¼ 7.6 Hz),
7.65–7.45 (m, 3H), 7.35–7.15 (m, 3H), 7.12–7.0 (m, 2H), 5.45 (t, 1H,
J ¼ 5.1 Hz), 4.95 (t, 1H, J ¼ 7.6 Hz), 4.10 (d, 2H, J ¼ 5.1 Hz), 3.5 (d,
2H, J ¼ 6.2 Hz); IR (neat): 1083, 1150, 1310, 2928 cmꢀ1. MS (Mþ): 304.
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8b: Colourless liquid. H NMR (CDCl3): ꢀ 7.90 (d, 2H, J ¼ 7.0 Hz),
7.70–7.50 (m, 3H), 5.55 (s, 2H), 5.20 (t, 1H, J ¼ 4.7 Hz), 3.60 (d, 2H,
J ¼ 4.7 Hz), 3.45 (d, 2H, J ¼ 4.7 Hz), 3.35 (d, 2H, J ¼ 4.7 Hz), 2.15–1.85
(m, 6H); IR (neat): 997, 1083, 1131, 1149, 1308, 2901 cmꢀ1. MS (Mþ):
308; HRMS (Mþþ1) Calcd. for C16H20SO4: 309.1160 found 309.1160.
9b: Colourless viscous liquid. 1H NMR (CDCl3): ꢀ 7.95 (d, 2H,
J ¼ 7.0 Hz), 7.65–7.45 (m, 3H), 7.40–7.15 (m, 10H), 5.70 (t, 1H,
J ¼ 4.7 Hz), 4.85 (d, 1H, J ¼ 8.2 Hz), 4.55 (d, 2H, J ¼ 7.0 Hz), 4.02–3.82
(m, 1H), 3.65 (d, 2H, J ¼ 4.7 Hz), 3.55 (d, 2H, J ¼ 4.7 Hz); IR (neat):
1024, 1083, 1151, 1309, 2929 cmꢀ1. MS (Mþ): 425; HRMS (Mþ) Calcd.
for C24H24SO5: 425.1422 found 425.1421.
10b: Colourless liquid. 1H NMR (CDCl3): ꢀ 7.90 (d, 2H, J ¼ 7.1 Hz),
7.65–7.45 (m, 3H), 7.35–7.15 (m, 5H), 5.40 (t, 1H, J ¼ 4.8 Hz), 4.40 (s,
2H), 3.90 (s, 2H), 3.50 (s, 2H), 3.35 (d, 2H, J ¼ 4.8 Hz), 1.25 (s, 3H); IR
(neat): 1043, 1083, 1123, 1150, 1309 cmꢀ1. MS (Mþ): 362.
ACKNOWLEDGMENT
Two of us (ChS., PSH) thank CSIR, New Delhi, for financial
assistance.
REFERENCES
1. (a) Greene, T.W.; Wuts, P.G.M. In Protective Groups in Organic
Synthesis; Wiley: N.Y. 1991, 2nd Ed.; (b) Kocienski, P.J. Protecting
Groups; Thieme: Stuttgart, 1994.