Chemistry Reference
In-Depth Information
N
t
-Bu
N
NH
NH
2
N
NO
3
(Me
2
N)
3
P
NP
N
N
P(NMe
2
)
3
N
Me
2
N
e
2
H
2
N
N
N
H
2
P(NMe
2
)
3
DBU (
1
)
TMG (
3
)
guanidinium nitrate (
4
)
TBD (
7
)
P
4
-
t-
Bu (
9
)
N
N
t
-Bu
N
i
-Pr
N
N
Me Me
Et
2
N
N
N
Me
2
N
e
2
i
-Pr
2
N
i
-Pr
2
N
N
Me
P
t-
Bu
6
5
DBN (
2
)
Barton's base
MTBD (
8
)
BEMP (
10
)
Figure 7.1
Structures of superbases
OH
HO
BnO
O
CHO
HO
BnO
OH
OBn
11
(+)-cyclophellitol (
14
)
THF, rt
CH
3
NO
2
> 60%
TMG (
3
)
O
BnO
NO
2
1. TMSCl
Et
3
N
N
BnO
BnO
OH
2. TsOH, rt
BnO
OH
OBn
55%
OBn
12
2 : 1
O
O
N
BnO
N
BnO
OTMS
OTMS
BnO
OH
BnO
OH
OBn
OBn
13
Scheme 7.1
Synthesis of (
รพ
)-cyclophellitol (14)
