HETEROCYCLES, Vol. 81, No. 8, 2010
1901
13C NMR (75 MHz, CDCl3) ꢀ 137.7, 137.1, 128.53(2C), 128.46(2C), 128.0(2C), 127.9, 127.8, 127.7(2C),
104.0, 85.7, 79.0, 71.7, 70.0, 64.1, 40.2; IR (neat, cm-1) 3447, 2925, 2872, 1455, 1361, 1104, 1043, 1026,
698, 607; MS (EI) m/z 254(1), 207(7), 181(4), 163(2), 146(2), 108(32), 107(25), 91(100), 79(41), 77(26),
65(12), 51(12); (DART) m/z 315 ([M+H]+); HRMS-DART calcd. for C19H23O4 ([M+H]+) 315.1596, found
315.1608.
((2R,3S,5S)-3,5-Bis(benzyloxy)tetrahydrofuran-2-yl)methanol (8b); colorless oil; [ꢁ]20 -34.7 (c 0.33,
D
1
CHCl3); H NMR (300 MHz, CDCl3) ꢀ 7.39-7.27 (m, 10H), 5.39 (dd, J = 5.2, 1.9 Hz, 1H), 4.73 (d, J =
11.9 Hz, 1H), 4.59 (d, J = 11.7 Hz, 1H), 4.51-4.41 (m, 1H), 4.49 (d, J = 11.9 Hz, 1H), 4.42 (d, J = 11.7
Hz, 1H), 4.20 (dt, J = 5.8, 4.3 Hz, 1H), 4.00-3.85 (m, 2H), 2.29 (ddd, J = 13.4, 6.7, 1.9 Hz, 1H), 2.19 (ddd,
13
J = 13.4, 5.2, 5.2 Hz, 1H); C NMR (75 MHz, CDCl3) ꢀ 137.9, 137.4, 128.6(2C), 128.4(2C), 128.00,
127.97(3C), 127.7, 127.6, 102.2, 79.4, 79.0, 71.8, 69.3, 61.8, 39.6; IR (neat, cm-1) 3444, 2921, 2873, 1061,
1026, 737, 698; MS (EI) m/z 254(2), 207(3), 206(3), 182(3), 181(4),163(4), 149(3), 146(2), 108(34),
107(31), 91(100), 79(39), 77(29), 57(14); (DART) m/z 315 ([M+H]+); HRMS-DART calcd. for C19H23O4
([M+H]+) 315.1596, found 315.1607.
((2S,3S,5R)-3,5-Bis(benzyloxy)tetrahydrofuran-2-yl)methanol (8c); colorless oil; [ꢁ]20 162.4 (c 1.70,
D
1
CHCl3); H NMR (300 MHz, CDCl3) ꢀ 7.40-7.25 (m, 10H), 5.24 (dd, J = 5.3, 1.5 Hz, 1H), 4.81 (d, J =
12.4 Hz, 1H), 4.60 (d, J = 12.0 Hz, 1H), 4.54 (d, J = 12.4 Hz, 1H), 4.49 (d, J = 12.0 Hz, 1H), 4.20 (dd, J =
8.1, 4.0 Hz, 1H), 4.08-4.00 (m, 1H), 3.82 (dd, J = 11.9, 2.9 Hz, 1H), 3.61 (dd, J = 11.9, 2.9 Hz, 1H), 2.26
13
(ddd, J = 13.4, 8.3, 5.4 Hz, 1H), 2.12 (ddd, J = 14.1, 3.4, 1.7 Hz, 1H); C NMR (75 MHz, CDCl3) ꢀ
138.0(2C), 128.4(2C), 128.3(2C), 127.8(2C), 127.7(2C), 127.5(2C), 102.7, 82.9, 78.1, 71.7, 68.9, 62.6,
39.1; IR (neat, cm-1) 3445, 2920, 2872, 1454, 1360, 1207, 1113, 1043, 1027, 737, 698; MS (EI) m/z
207(11), 206(2), 10(21), 107(19), 91(100), 79(26), 77(18), 65(11), 51(10); (DART) m/z 315 ([M+H]+);
HRMS-DART calcd. for C19H23O4 ([M+H]+) 315.1596, found 315.1610.
2-Deoxy-D-ribose
To a solution of 8a (16 mg, 0.051 mmol) in EtOH (1 mL) was added Pd/C (2 mg) at rt, then the reaction
vessel was evacuated and back-filled with H2 (5x). After stirring for 58 h at rt, the mixture was filtered
over a pad of Celite®, which was washed with MeOH. The filtrate was concentrated in vacuo. The crude
material was purified by silica gel column chromatography (MeOH-CHCl3 = 1:3) to afford
2-deoxy-D-ribose (6.6 mg, 97% yield) as a colorless amorphous solid.
1
2-Deoxy-D-ribose; colorless amorphous solid; [ꢁ]20 -38.6 (c 0.33, MeOH); H NMR (300 MHz,
D
CD3OD) ꢀ difficult to assign the spectra; 13C NMR (75 MHz, CD3OD) the equilibrium mixture of
pyranose and furanose form and those epimer at C1; ꢀ 99.5, 99.4, 95.2, 93.1, 87.9, 86.7, 72.8, 72.5, 69.4,
69.2, 68.3, 66.6, 66.2, 64.5, 64.3, 63.2, 43.5, 43.1, 37.3, 36.6.