The NMR spectra indicated that compound 1 was present as a mixture of two anomers
in D2O similarly to the case in DMSO-d6,3) although the ratio of the two anomers in D2O
(1.0:1.1) was different from that in DMSO-d6. The 1JC,H values (171 Hz and 161 Hz)
observed at the anomeric carbons of minor and major anomers suggested  and 
anomers (Bock & Pedersen, 1974), respectively, but relative stereochemistry around
the six-membered ring of each anomer could not be confirmed due to ambiguous J
values among the ring protons.
Compound 1: ESI-TOFMS m/z 359 (M+Na)+; H
(CDCl3, 500 MHz): 5.06 (1H, H-1), 4.11 (1H, H-5), 4.17 (1H, H-3’), 4.17 (1H, H-3”), 3.84
(1H, H-2), 3.34 (2H, H-6), 2.66 (1H, H-2’a), 2.61 (2H, H-2”), 2.60 (1H, H-2’b), 2.06 (1H,
H-3a), 1.74 (1H, H-3b), 1.59 (2H, H-4), 1.43 (3H, H-4’), 1.43 (3H, H-4”) (minor anomer);
4.93 (1H, H-1), 4.17 (1H, H-3’), 4.17 (1H, H-3”), 4.04 (1H, H-2), 3.77 (1H, H-5), 3.42 (1H,
H-6a), 3.34 (1H, H-6b), 2.72 (1H, H-2’a), 2.61 (2H, H-2”), 2.60 (1H, H-2b’), 1.92 (1H,
H-3a), 1.84 (1H, H-3b), 1.51 (1H, H-4a), 1.47 (1H, H-4b), 1.43 (3H, H-4’), 1.43 (3H,
H-
C
(CDCl3, 125 MHz): 173.0 (C1”), 172.6 (C1’), 151.9 (NC),
151.9 (NC), 92.9 (C1), 68.3 (C5), 48.8 (C3’), 48.8(C3”), 48.0 (C2), 44.2 (C6), 43.4 (C2”),
43.2 (C2’), 23.3 (C4), 22.3 (C3), 21.3 (C4’), 21.3 (C4”) (minor anomer); 173.4 (C1’),
173.0 (C1”), 151.9 (NC), 151.9 (NC), 95.0 (C1), 75.9 (C5), 49.0 (C3’), 48.8 (C3”), 48.8
(C2), 44.2 (C6), 43.4 (C2’), 43.4 (C2”), 27.3 (C3), 22.9 (C4), 21.3 (C4’), 21.3 (C4”)
(major anomer).
Bock, K. & Pedersen, C. a study of
13
Soc. Perkin Trans II 293-297 (1974).
CH coupling constants in hexopyranoses. J Chem