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CN
NH
2
H
O
1. BrCH
2
CO
2
t
Bu
O
H
O
O
O
6
6
6'
6'
2. LiAlH
4
Fruc
3xOBn
Gluc
3xOBn
Gluc
3xOBn
Fruc
3xOBn
23
62
Ph
3
P
imid.
I
2
R
I
N
NH
2
O
O
6
6'
O
O
OBn
O
6
6'
O
BnO
Gluc
3xOBn
Fruc
3xOBn
O
OBn
BnO
OBn
63
OBn
64.
R = H
65.
R = substituent
RX/bas
e
Scheme 13 Preparation of the sucrose aza-crown with the nitrogen atom not protected
(64) and its analogs (65).
t
BuO
1. BrCH
2
CO
2
tBu
2. F
(-)
O
X
Y
6
BnO
6'
O
6'
O
O
O
BnO
3. [O]
6
O
OBn
Fruc
3xOBn
Gluc
3xOBn
BnO
OBn
24b
OBn
reductive
66
X = Y = O
(48-50, 53,
58, 64, 65)
X = Y = NBn
(
57
, 60, 61)
amination
X = Y ???
t
NHBn
BuO
H
O
NHBn
O
O
Bn
O
N
O
Bn
N
6
6'
6
26b
6'
Fruc
3xOBn
Fruc
3xOBn
Gluc
3xOBn
Gluc
3xOBn
as for
Ph
3
P
imid.
I
2
68
67
24b
Bn
Bn
N
N
Bn
Bn
O
N
N
O
6
BnO
6'
6
6'
BnO
O
O
O
BnO
O
BnO
OBn
O
O
OBn
BnO
BnO
OBn
OBn
OBn
69
OBn
70
Scheme 14 Preparation of 'unsymmetrical' sucrose macrocycles.
6-OH and 6
0
-OH; 2. methylation of the remaining six hydroxyl groups;
3. removal of both silyl blocks).
Reaction of activated (as dimesylate) diol 71 with ortho- meta- and para-
nitrophenols afforded the corresponding di-ethers which were converted
into diamines 72. Both amino-functions were coupled with the acid
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