Z. Hricovíniová / Carbohydrate Polymers 144 (2016) 297–304
299
3.68 (m, H-1ꢀ␣a), 3.67 (m, H-4), 3.66 (m, H-3␣), 3.63 (m, H-5␣a),
3.62 (m, H-4␣), 3.51 (m, H-3), 3.50 (m, H-1ꢀb), 3.48 (m, H-5␣b),
3.47 (m, H-2␣), 3.43 (m, H-1ꢀ␣b), 3.38 (m, H-2), 3.26 (m, H-5b),
1.60 (m, H-2ꢀ␣), 1.31 (m, H-3ꢀ␣), 1.30 (m, H-7ꢀ␣), 1.28 (m,
H-6ꢀ␣), 1.26 (m, H-4ꢀ␣, H-5ꢀ␣), 0.88 (m, CH3 ␣). 13C NMR
(150.84 MHz, CDCl3): 102.93 (C-1), 98.39 (C-1␣), 75.65 (C-3),
74.95 (C-3␣), 72.83 (C-2), 72.22 (C-2␣), 70.10 (C-1ꢀ), 69.95 (C-
4␣), 69.66 (C-4), 68.47 (C-1ꢀ␣), 65.00 (C-5), 61.70 (C-5␣), 29.46
(C-2ꢀ␣), 29.44 (C-3ꢀ␣), 29.31 (C-4ꢀ␣, C-5ꢀ␣), 26.08 (C-7ꢀ␣),
25.98 (C-7ꢀ), 22.66 (C-6ꢀ␣), 14.10 (CH3 (C-8ꢀ␣)).
3.69 (m, H-1ꢀ␣a, H-4), 3.67 (m, H-3␣), 3.64 (m, H-5␣a), 3.63 (m,
H-4␣), 3.53 (m, H-3), 3.50 (m, H-5␣b, H-1ꢀb), 3.48 (m, H-2␣),
3.44 (m, H-1ꢀ␣b), 3.40 (m, H-2), 3.28 (m, H-5b), 1.62 (m, H-
2ꢀ␣), 1.32 (m, H-11ꢀ␣), 1.28 (m, H-3ꢀ␣ − H-10ꢀ␣), 0.88 (m, CH3
␣). 13C NMR (150.84 MHz, CDCl3): 102.89 (C-1), 98.36 (C-1␣),
75.54 (C-3 ), 75.02 (C-3 ␣), 72.78 (C-2), 72.25 (C-2␣), 70.09 (C-
1ꢀ), 69.96 (C-4␣), 69.67 (C-4), 68.48 (C-1ꢀ␣), 64.92 (C-5), 61.70
(C-5␣), 29.39 (C-2ꢀ␣), 29.36 (C-3ꢀ␣−C-10ꢀ␣), 26.01 (C-11ꢀ␣),
14.13 (CH3 (C-12ꢀ␣)).
2.11. 1-Tetradecyl ˛/ˇ-d-xylopyranoside (6)
2.7. 1-Nonyl ˛/ˇ-d-xylopyranoside (2)
Yield 40%; white solid; Rf 0.87 (solvent A); ˛/ˇ ratio 1:0.43;
[␣]D20 +7.8 (c 1, CHCl3); HRMS m/z: calcd for C19H38O5Na [M+Na]+:
369.2617; found 369.2662. 1H NMR (599.84 MHz, CDCl3): 4.79 (d,
H-1␣), 4.34 (d, H-1), 4.01 (dd, H-5a), 3.84 (m, H-1ꢀa), 3.72 (m,
H-1ꢀ␣a), 3.71 (m, H-4), 3.66 (m, H-3␣), 3.65 (m, H-4␣, H-5␣a),
3.56 (m, H-3), 3.51 (m, H-5␣b), 3.50 (m, H-1ꢀb), 3.47 (m, H-2␣),
3.43 (m, H-1ꢀ␣b), 3.42 (m, H-2), 3.33 (m, H-5b), 1.61 (m, H-2ꢀ␣),
20
Yield 68%; yellow oil; Rf 0.81 (solvent A); ˛/ˇ ratio 1:0.65; [␣]D
+44.5 (c 1, CHCl3); HRMS m/z: calcd for C14H28O5Na [M+Na]+:
299.1834; found 299.1821. 1H NMR (599.84 MHz, CDCl3): 4.79 (d,
H-1␣), 4.31 (d, H-1), 3.99 (dd, H-5a), 3.83 (m, H-1ꢀa), 3.71
(m, H-4), 3.70 (m, H-1ꢀ␣a), 3.67 (m, H-3␣), 3.66 (m, H-4␣), 3.65
(m, H-5␣a), 3.55 (m, H-3), 3.51(m, H-1ꢀb, H-5␣b), 3.48 (m, H-
2␣), 3.44 (m, H-1ꢀ␣b), 3.41 (m, H-2), 3.31 (m, H-5b), 1.61 (m,
H-2ꢀ␣), 1.31 (m, H-3ꢀ␣), 1.29 (m, H-4ꢀ␣, H-5ꢀ␣), 1.27 (m, H-
6ꢀ␣), 1.27 (m, H-7ꢀ␣), 0.88 (m, CH3 ␣). 13C NMR (150.84 MHz,
CDCl3): 102.73 (C-1), 99.31 (C-1␣), 75.16 (C-3 ␣), 72.61 (C-2),
72.31 (C-2␣), 70.02 (C-1ꢀ), 69.93 (C-4␣), 69.67 (C-4), 68.46 (C-
1ꢀ␣), 64.65 (C-5), 61.67 (C-5␣), 29.56 (C-2ꢀ␣), 29.48 (C-3ꢀ␣),
29.31 (C-4ꢀ␣−C-6ꢀ␣), 26.11 (C-8ꢀ␣ ), 22.69 (C-7ꢀ␣), 14.07 (CH3
(C-9ꢀ␣)).
1.32 (m, H-13ꢀ␣), 1.28 (m, H-3ꢀ␣−H-12ꢀ␣), 0.88 (t, CH3 ␣). 13
C
NMR (150.84 MHz, CDCl3): 102.61 (C-1), 98.27 (C-1␣), 75.28 (C-
3␣), 74.86 (C-3), 72.41 (C-2 ␣), 69.94 (C-1ꢀ), 69.93 (C-4␣), 69.65
(C-4), 68.51 (C-1ꢀ␣), 64.44 (C-5), 61.70 (C-5␣), 29.57 (C-2ꢀ␣),
29.46 (C-3ꢀ␣−C-12ꢀ␣), 25.77 (C-13ꢀ␣), 14.11 (CH3 (C-14ꢀ␣)).
2.12. 1-Octyl ˛-d-lyxopyranoside (7)
20
Yield 71%; clear oil; Rf 0.83 (solvent A); [␣]D
+38.0 (c 1,
2.8. 1-Decyl ˛/ˇ-d-xylopyranoside (3)
CHCl3); HRMS m/z: calcd for C13H26O5Na [M+Na]+: 285.1678;
found 285.1689. 1H NMR (599.84 MHz, CDCl3): 4.72 (d, H-1),
3.91(m, H-4), 3.89 (m, H-2), 3.78 (m, H-3), 3.74 (dd, H-5a), 3.68
(m, H-1ꢀa), 3.49 (dd, H-5b), 3.40 (m, H-1ꢀb), 1.56 (m, H-2ꢀ), 1.31
(m, H-3ꢀ), 1.30 (H-6ꢀ), 1.29 (m, H-4ꢀ, H-5ꢀ), 0.88 (t, CH3). 13C NMR
(150.84 MHz, CDCl3): 100.10 (C-1), 71.77 (C-3), 70.62 (C-2), 68.17
(C-1ꢀ), 67.34 (C-4), 62.50 (C-5), 31.87 (C-7ꢀ), 29.45 (C-2ꢀ), 29.42 (C-4ꢀ,
C-5ꢀ), 26.11 (C-3ꢀ), 22.67 (C-6ꢀ), 14.32 (CH3 (C-8ꢀ␣)).
Yield 55%; white solid; Rf 0.73 (solvent A); ˛/ˇ ratio 1:0.63;
20
[␣]D
+31.7 (c 1, CHCl3); HRMS m/z: calcd for C15H30O5Na
[M+Na]+: 313.1991; found 313.2008. 1H NMR (599.84 MHz, CDCl3):
4.79 (d, H-1␣), 4.33 (d, H-1), 4.01 (dd, H-5a), 3.83 (m, H-1ꢀa),
3.72 (m, H-4), 3.71 (m, H-1ꢀ␣a), 3.66 (m, H-3␣, H-4␣, H-5␣a),
3.57 (m, H-3), 3.51 (m, H-5␣b), 3.50 (m, H-1ꢀb), 3.47 (m, H-
2␣), 3.43(m, H-2, H-1ꢀ␣b), 3.33 (m, H-5b), 1.61 (m, H-2ꢀ␣),
1.33 (m, C-9ꢀ␣), 1.30 (m, H-3ꢀ␣−H-8ꢀ␣), 0.88 (m, CH3 ␣). 13
C
2.13. 1-Nonyl ˛-d-lyxopyranoside (8)
NMR (150.84 MHz, CDCl3): 102.65 (C-1), 98.27 (C-1␣), 75.28 (C-
3␣), 74.95 (C-3), 72.49 (C-2), 72.38 (C-2␣), 69.96 (C-4␣), 69.94
(C-1ꢀ), 69.69 (C-4), 68.46 (C-1ꢀ␣), 64.48 (C-5), 61.67 (C-5␣),
29.49 (C-2ꢀ␣), 29.45 (C-3ꢀ␣−C-8ꢀ␣), 26.14 (C-9ꢀ␣), 14.13 (CH3
(C-10ꢀ␣)).
20
Yield 67%; yellow oil; Rf 0.81 (solvent A); [␣]D +44.5 (c 1,
CHCl3); HRMS m/z: calcd for C14H28O5Na [M+Na]+: 299.1834;
found 299.1845. 1H NMR (599.84 MHz, CDCl3): 4.72 (d, H-1), 3.89
(m, H-4), 3.88 (m, H-2), 3.83 (m, H-3), 3.75 (dd, H-5a), 3.71 (m,
H-1ꢀa), 3.53 (dd, H-5b), 3.41 (m, H-1ꢀb), 1.58 (m, H-2ꢀ), 1.31 (m,
H-3ꢀ), 1.30 (m, H-4ꢀ−H-7ꢀ), 1.27 (m, H-8ꢀ), 0.88 (t, CH3). 13C NMR
(150.84 MHz, CDCl3): 100.04 (C-1), 71.83 (C-3), 70.52 (C-2), 68.41
(C-1ꢀ), 68.04 (C-4), 62.74 (C-5), 31.90 (C-8ꢀ), 29.45 (C-2ꢀ), (C-4ꢀ−C-
6ꢀ), 26.13 (C-3ꢀ), 22.69 (C-7ꢀ), 14.32 (CH3 (C-9ꢀ␣)).
2.9. 1-Undecyl ˛/ˇ-d-xylopyranoside (4)
20
Yield 51%; yellow oil; Rf 0.8 (solvent A); ˛/ˇ ratio 1:0.55; [␣]D
+41.4 (c 1, CHCl3); HRMS m/z: calcd for C16H32O5Na [M+Na]+:
327.2147; found 327.2165. 1H NMR (599.84 MHz, CDCl3): 4.78 (d,
H-1␣), 4.29 (d, H-1), 3.95 (dd, H-5a), 3.81 (m, H-1ꢀa), 3.68 (m,
H-1ꢀ␣a), 3.67 (m, H-4), 3.64 (m, H-3␣), 3.62 (m, H-5␣a), 3.61 (m,
H-4␣), 3.51 (m, H-3), 3.49 (m, H-5␣b, H-1ꢀb), 3.46 (m, H-2␣),
3.42 (m, H-1ꢀ␣b), 3.38 (m, H-2), 3.26 (m, H-5b), 1.61 (m, H-2ꢀ␣),
1.56 (m, H-2ꢀ), 1.32 (m, C-10ꢀ␣), 1.30 (m, H-3ꢀ␣ − H-9ꢀ␣), 0.88
(m, CH3 ␣). 13C NMR (150.84 MHz, CDCl3): 102.89 (C-1), 98.38
(C-1␣), 75.53 (C-3 ), 74.98 (C-3 ␣), 72.76 (C-2), 72.23 (C-2␣),
70.09 (C-1ꢀ), 69.93 (C-4␣), 69.64 (C-4), 68.46 (C-1ꢀ␣), 64.91 (C-
5), 61.68 (C-5␣), 29.48 (C-2ꢀ␣), 29.37 (C-3ꢀ␣−C-9ꢀ␣), 25.99
(C-10ꢀ␣), 14.14 (CH3 (C-11ꢀ␣)).
2.14. 1-Decyl ˛-d-lyxopyranoside (9)
20
Yield 62%; white solid; Rf 0.75 (solvent A); [␣]D
+22.2 (c
1, CHCl3); HRMS m/z: calcd for C15H30O5Na [M+Na]+: 313.1991;
found 313.2011. 1H NMR (599.84 MHz, CDCl3): 4.72 (d, H-1), 3.90
(m, H-4), 3.89 (m, H-2), 3.78 (m, H-3), 3.73 (dd, H-5a), 3.67 (m,
H-1ꢀa), 3.48 (dd, H-5b), 3.41 (m, H-1ꢀb), 1.58 (m, H-2ꢀ), 1.31 (m,
H-3ꢀ), 1.30 (m, H-4ꢀ−H-9ꢀ), 0.88 (t, CH3). 13C NMR (150.84 MHz,
CDCl3): 100.09 (C-1), 71.83 (C-3), 70.65 (C-2), 68.20 (C-1ꢀ), 67.40 (C-
4), 62.51 (C-5), 31.93 (C-9ꢀ), 29.51 (C-2ꢀ), 29.47 (C-4ꢀ−C-7ꢀ), 26.12
(C-3ꢀ), 22.80 (C-8ꢀ), 14.12 (CH3 (C-10ꢀ␣)).
2.10. 1-Dodecyl ˛/ˇ-d-xylopyranoside (5)
2.15. 1-Undecyl ˛-d-lyxopyranoside (10)
Yield 43%; white flaky solid; Rf 0.77 (solvent A); ˛/ˇ ratio
20
20
1:0.47; [␣]D +36.6 (c 1, CHCl3); HRMS m/z: calcd for C17H34O5Na
Yield 55%; yellowish solid; Rf 0.78 (solvent A); [␣]D +15.6 (c
[M+Na]+: 318.2406; found 318.2431. 1H NMR (599.84 MHz, CDCl3):
1, CHCl3); HRMS m/z: calcd for C16H32O5Na [M+Na]+: 327.2147;
4.78 (d, H-1␣), 4.28 (d, H-1), 3.98 (dd, H-5a), 3.82 (m, H-1ꢀa),
found 327.2163. 1H NMR (599.84 MHz, CDCl3): 4.71 (d, H-1), 3.85