10.1071/CH09015_AC © CSIRO 2009 Accessory Publication: Australian Journal of Chemistry, 2009, 62(6), 546–552
Accessory Publication
An Improved Synthetic Route to the Potent Angiogenesis Inhibitor Benzyl Manα α(1→ →3)-Manα α(1→ →3)-Manα α(1→ →3)-Manα α(1→ →2)-Man Hexadecasulfate∗
Ligong Liu,A,B Ken D. Johnstone,A Jon K. Fairweather,A,C Keith Dredge,A Vito FerroA,D,E A
Drug Design Group, Progen Pharmaceuticals Limited, Darra, Qld 4076, Australia.
B
Present address: Centre for Drug Design and Development, Institute for Molecular
Bioscience, University of Queensland, Brisbane, Qld 4072, Australia. C
Present address: Chemical Analysis Pty Ltd, 41 Greenaway Street, Bulleen, VIC 3105,
Australia. D
Present address: CRC for Polymers, School of Physical and Chemical Sciences,
Queensland University of Technology, GPO Box 2434, Brisbane, Qld 4001, Australia. E
Corresponding author. Email:
[email protected]
Content ∗
Dedicated to Professor Robert (Bob) V. Stick on the occasion of his retirement.
S1
1
H NMR spectrum of compound 20
S3
13
C NMR spectrum of compound 20
S4
1
H NMR spectrum of compound 22
S5
13
C NMR spectrum of compound 22
S6
1
H NMR spectrum of compound 24
S7
13
C NMR spectrum of compound 24
S8
1
H NMR spectrum of compound 26
S9
13
C NMR spectrum of compound 26
S10
S2
20
9.0 ppm (t1)
8.0
7.0
6.0
S3
5.0
4.0
3.0
20
170 ppm (t1)
160
150
140
130
120
110
S4
100
90
80
70
22
8.0
7.0
6.0
5.0
ppm (f1)
S5
4.0
3.0
22
180 ppm (f1)
170
160
150
140
130
120
110
S6
100
90
80
70
60
50
24
8.0
7.0
6.0
5.0
ppm (t1)
S7
4.0
3.0
24
190 180 ppm (t1)
170
160
150
140
130
120
110
100
S8
90
80
70
60
50
40
30
20
10
26
8.0
7.0
6.0
5.0
ppm (t1)
S9
4.0
3.0
26
170 ppm (t1)
160
150
140
130
120
110
S10
100
90
80
70
60
