Chemistry Reference
In-Depth Information
2. F
(-)
3. propargyl
bromide/NaH
1. conversion
into azide
OH
OBn
6
TBDPSO
O
N
3
O
BnO
O
Gluc
6
6'
6'
Fruc
O
Fruc
3xOH
Gluc
3xOH
BnO
BnO
BnO
OBn
'click'
79
24b
O
Bn
BnO
O
N
3
OBn
N
NN
O
O
BnO
OBn
O
O
6'
O
OBn
BnO
O
6
BnO
OBn
Fruc
3xOH
O
Gluc
3xOH
O
NN
BnO
N
OBn
O
82
OBn
80
+
N
'click'
N
N
N
N
N
O
O
6
6
N
N
6
'
+
6'
N
Fruc
3xOH
Gluc
3xOH
Fruc
3xOH
Gluc
3xOH
O
O
81a
81b
OBn
O
O
BnO
O
OBn
BnO
OBn
OBn
83
Scheme 17 Synthesis of sucrose macrocycles by 'click chemistry'.
TBDPSO
N
3
BnO
O
1.
24b
O
O
O
O
OBn
BnO
BnO
BnO
BnO
84
2. F
(-)
BnO
OBn
BnO
BnO
BnO
BnO
OBn
OBn
O
O
O
O
1. MsCl, Et
3
N
2.
O
N
O
BnO
BnO
NH
2
N
N
H
2
N
H
H
O
O
+
NH
3
O
Cl
H
H
O
N
Ph
CO
2
Me
N
BnO
BnO
O
N
O
template
O
O
O
O
OBn
OBn
BnO
BnO
BnO
BnO
OBn
BnO
86
=
N
,
85
Scheme 18 Synthesis of dimeric sucrose macrocycles.
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