E. V. Evtushenko
374
Benzyl 3-O-benzoyl-α-L-rhamnopyranoside
Yield 154 mg (86%). Rf 0.56, mp 67–69◦С (from EtAc-hexane), [α]D −79.1◦
(c 0.6, CHCl3).1H NMR δ: 8.12–8.07 (m, 2H, PhH), 7.65–7.56 (m, 1H, PhH),
7.51–7.43 (m, 2H, PhH), 7.40–7.30 (m, 5H, PhH), 5.36 (dd, 1H, J2,3 = 3.2 Hz,
J3,4 = 9.5 Hz, H-3), 4.92 (d, 1H, J1,2 = 1.8 Hz, H-1), 4.78 и 4.58 (2d, 2H, J =
20
12.0 CH2PH), 4.22 (dd, 1H, H-2), 3.87 (m, 2H, H-4, H-5), 1.41 (d, 3H, J5,6
=
5.9 Hz, CH3). 13C NMR δ: 167.0, 137.0, 133.5, 130.1, 129.9, 129.5, 128.5, 128.1,
98.7, 75.0, 71.5, 69.9, 69.2, 68.9, 17.6. Anal. Calcd. for C20 H22O6: C, 67.03; H,
6.19. Found: C, 66.98; H, 6.11.
Methyl 2-O-benzoyl-β-L-rhamnopyranoside
Yield 107 mg (76%). Rf 0.46 mp 99–100◦С (from EtAc-hexane), [α]D
20
1
+82.5◦ (c 0.4, CHCl3). H NMR δ: 8.10–8.06 (2H, m, PhH), 7.60–7.52 (1H, m,
Ph-H), 7.47–7.37 (2H, m, PhH), 5.57 (dd, 1H, J1,2 = 0.7 Hz, J2,3 = 3.3 Hz, H-2),
4.52 (d, 1H, H-1), 3.76 (dd, 1H, J3,4 = 9.2 Hz, H-3), 3.54 (t, 1H, J4,5 = 9.0 Hz,
H-4), 3.50 (s, 3H, OCH3), 3.39 (m, 1H, H-5), 1.43 (d, 3H, J5,6 = 6.1 Hz, CH3).
13C NMR δ: 167.0, 133.3, 130.1, 128.4, 100.0, 73.5, 73.4, 72.2, 72.1, 57.1, 17.6.
Anal. Calcd. for C14H18O6: C, 59.57; H, 6.43. Found: C, 59.50; H, 6.38.
Methyl 3-O-benzoyl-α-D-fucopyranoside
Yield 120 mg (85%). Rf 0.47, [α]D +136.7◦ (c 0.8, CHCl3). H NMR δ:
8.12–8.07 (2H, m, Ph), 7.60–7.55 (m, 1H, PhH), 7.47–7.42 (m, 2H, PhH), 5.29
(dd, 1H, J2,3 = 10.3 Hz, J3,4 = 3.2 Hz, H-3), 4.85 (d, 1H, J1,2 = 3.9 Hz, H-1),
4.14 (dd, 1H, Н-2), 4.07 (m, 1H, J5,6 = 6.7 Hz, H-5), 3.98 (m, 1H, H-4), 3.46
(s, 3H, OCH3), 1.31 (d, 3H, CH3). 13C NMR δ: 166.5, 133.5, 130.0, 128.5, 99.8,
74.7, 71.0, 67.2, 65.8, 55.6, 16.1. Anal. Calcd. for C14H18O6: C, 59.57; H, 6.43.
Found: C, 59.52; H, 6.48.
20
1
Methyl 3-O-benzoyl-β-D-fucopyranoside
Yield 122 mg (86%). Rf 0.44, mp 142–143◦С (from EtAc-hexane), [α]D
20
1
+52.4◦ (c 0.6, CHCl3). H NMR δ: 8.12–8.06 (2H, m, Ph), 7.59–7.53 (m, 1H,
PhH), 7.46–7.41 (m, 2H, PhH), 5.00 (dd, 1H, J2,3 = 10.2 Hz, J3,4 = 3.2 Hz,
H-3), 4.22 (d, 1H, J1,2 = 7.8 Hz, H-1), 3.90 (m, 1H, Н-4), 3.88 (dd, 1H, H-2),
3.70 (m, 1H, H-5), 3.52 (s, 3H, OCH3), 1.28 (d, 3H, J5,6 = 6.3 Hz, H-6 CH3).
13C NMR δ: 166.5, 133.4, 129.9, 128.5, 104.2, 76.3, 70.6, 70.2, 69.4, 57.2, 16.2.
Anal. Calcd. for C14H18O6: C, 59.57; H, 6.43. Found: C, 59.46; H, 6.40.
Methyl 3-O-benzoyl-α-L-arabinopyranoside
Yield 108 mg (81%). Rf 0.33, mp 140–141◦С, (from EtAc-hexane), [α]D
20
1
+48.6◦ (c 0,7, CHCl3). H NMR δ: 8.14–8.06 (2H, m, Ph-H), 7.64–7.56 (m, 1H,
PhH), 7.51–7.42 (m, 2H, PhH), 5.14 (dd, 1H, J2,3 = 9.5 Hz, J3,4 = 3.4 Hz, H-3),
4.29 (d, 1H, J1,2 = 7.1 Hz, H-1), 4.21 (m, 1H, H-4), 4.08 (dd, 1H, J4,5a = 2.9 Hz,
J5a,5b = 12.7 Hz, H-5a) 4.02 (dd, 1H, H-2), 3.70 (dd, 1H, J4,5b = 1.5 Hz, H-5b),