N
X
C
O
N
S
Hal
Solvents
Natural
Products
P Si
C
C
C C
C
C
248
5 1 H NMR
248
5 1 H NMR
O
OH
HO
OH
OH
OH
H
H
H
O
OH
HO
OH
OH
OH
H
H
H
O
OH OH
OH
HO
HO
H
H
H
H
H
O
HO
OH
OH
HO
OH
H
H
H
H
H
O
HO
OH
OH
HO
H
OH
H
H
H
H
D 2 O
3 J bc 7.8
3 J ce 9.5
3 J eg 9.5
3 J gi 9.5
3 J ij 2.8
3 J ik 5.7
2 J jk -12.8
D 2 O
3 J bc 3.6
3 J ce 9.5
3 J eg 9.5
3 J gi 9.5
3 J ij 2.8
3 J ik 5.7
2 J jk -12.8
DMSO
3 J ab
6.5
3 J cd 4.5–6
3 J ef 4.5–6
3 J gh 4.5–6
3 J jl
5.5
3 J kl
6.0
DMSO
3 J ab 4.5
3 J cd 6.8
3 J ef 4.8
3 J gh 5.5
3 J jl 5.7
3 J kl 6.2
2 J ab -11.0
3 J cd 7.1
3 J de 5.9
3 J ef 2.3
3 J eg 3.6
2 J fg -11.3
DMSO
3 J ab 7.4 c
3 J ac 5.4 c
2 J bc -11.3 d
3 J de 6.8 c
3 J df 10.1 d
3 J fg 5.8 c
3 J fh 4.0 d
3 J hi 3.8 c
3 J hj 1.9 d
3 J hk 1.6 d
2 J jk -12.1 d
D 2 O* DMSO
a
6.58
b 4.51
4.27
c 3.13
2.89
d
4.84
e 3.37
3.10
f
4.84
g 3.30
3.10
h
4.84
i 3.35
3.04
j 3.60
3.42
k 3.75
3.66
l
4.48
D 2 O* DMSO
a
6.20
b 5.09
4.91
c 3.41
3.10
d
4.84
e 3.61
3.42
f
4.64
g 3.29
3.04
h
4.77
i 3.72
3.57
j 3.72
3.57
k 3.63
3.42
l
4.37
D 2 O a DMSO b
a
4.48
b 3.68
3.39
c 3.53
3.25
d 3.76
3.55
e
4.23
f 3.86
3.58
g
4.38
h 3.96
3.62
i
4.32
j 4.00
3.77
k 3.68
3.41
l
5.14
(in DMSO ≈ 80%)
(* relative to internal
acetone at δ = 2.12)
(* relative to internal
acetone at δ = 2.12)
a 25% β-D
b 75% β-D
c at 25 o C
d at 70 o C
(in DMSO ≈ 20%)
(in DMSO, 20% α-D)
(in DMSO, 55% β-D)
a
b
b
a
a
c
c
d
d
d
e
f
f
f
j
k
l
g
h
h
h
l
l
j,k
j,k
b,c
i
i
i
e
e
g
g
3.52, 3.40
3.40, 3.23
3.48, 3.37
3.69
3.72
3.79
3.53
3.77
3.80
a,b
c
d
e
f,g