N
X
C
O
N
S
Hal
Solvents
Natural
Products
P Si
C
C
C C
C
C
244
5 1 H NMR
244
5 1 H NMR
+
H 3 N
O
–
O
HO
+
H 3 N
OH
O
HO
7.63
4.44
3.58
4.82
4.24
1.32
1.67
3 J ab 5.5
3 J bc 4.5
3 J cd 6.5
3 J bc 4.9
3 J cd 6.6
(in TFA)
a
b
b
d
d
c
c
+
H 3 N
OH
O
HS
Cl
–
+
H 3 N
OH
O
+
H 3 N
O
–
O
+
H 3 N
OH
O
HS
+ H 3 N
O
–
O
S
+
H 3 N
OH
O
S
7.58
7.3
7.4
7.6
7.33
7.73
1.84
2.27
2.13
2.96
2.64
3.36
3.41
3.37
3.64
3.11
3.27
4.68
4.68
3.98
7.32
7.36
7.42
4.67
3.85
4.37
3.97
3.14
3.18
3.02
3.10
2.50
2.65
2.1
2.2
3 J bc 5.0
3 J bd 5.0
2 J cd -15.0
3 J bc 4.4
3 J bd 5.6
3 J cd -15.1
3 J ab 5.5
3 J bc 7.7
3 J bd 4.4
2 J cd -15.7
3 J ce 6.5*
3 J de 6.5*
3 J bc 7.0
3 J bd 5.5
3 J ce 7.6
3 J de 7.6
3 J ab 5.3
3 J bc 5.0*
3 J bd 5.0*
2 J cd -15.5
3 J ce 9.1*
3 J de 9.1*
3 J bc 8.5
3 J bd 4.5
2 J cd -14.5
3 J bc 9.0
3 J bd 5.1
2 J cd -15.5
(in TFA)
* average
(in TFA)
* average
(in TFA)
(in H 2 O, pH 7.0)
(in D 2 O)
(in H 2 O, pH 7.0)
(in H 2 O, pH 7.0)
a
a
b
b
b
b
b
c
d
c
d
c
d
c
d
f
f
e
e
e
a
b
b
c
d
c
d
c
d
+
H 3 N
O
–
O
HO
+
H 3 N
OH
O
HO
4.51
4.56
3.94
3.98
7.70
4.65
3.83
3 J ab ≈6
3 J bc 4.0*
3 J bd 4.0*
2 J cd -13.5
3 J bc 5.5
3 J bd 4.0
2 J cd -12.3
(in H 2 O, pH 7.0)
(in H 2 O, pH 7.0)
(in TFA)
* average
a
b
b
c
d
c
d
+
H 3 N
O
–
O
HS