Ejoc 201201342 SM Miscellaneous Information

Eur. J. Org. Chem. 2013 WILEY-VCH Verlag GmbH & Co.
KGaA, 69451 Weinheim, 2013 ISSN 1434193X

SUPPORTING INFORMATION
DOI: 10.1002/ejoc.201201342
Title: A Divergent and Stereoselective Approach for the Syntheses of Some Polyhydroxylated Indolizidine and Pyrrolizidine
Iminosugars
Author(s): Anugula Rajender, Jalagam Prasada Rao, Batchu Venkateswara Rao*
TBSO
NHBn
HO
O
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
H-NMR of Compound 15
2.5
2.0
1.5
1.0
0.5
0.0
TBSO
NHBn
HO
O
170
160
150
140
130
120
110
100
13
90
80
70
60
C-NMR of compound 15
50
40
30
20
10
-10
TBSO Cbz
Si
7.5
7.0
6.5
6.0
NBn
5.5
5.0
4.5
4.0
TBSO Cbz
Si
175
150
3.0
2.5
2.0
1.5
1.0
0.5
0.0
125
13
NBn
O
O
200
3.5
100
75
50
25
TBSO
HN
HO
O
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
TBSO
HN
HO
O
200
175
150
125
13
100
75
50
25
TBSO
N
O
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
TBSO
N
O
160
150
140
130
120
110
100
90
13
80
70
60
50
40
30
20
10
-10
HO
HO
7.5
7.0
6.5
6.0
OH
5.5
5.0
4.5
HO
HO
160
150
140
130
120
110
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
H-NMR of Compound 9
N
OH
100
13
90
80
70
60
C-NMR of compound 9
50
40
30
20
10
Bn Cbz
OH N
TBSO
O
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
50
40
1.5
1.0
0.5
0.0
-0.5
H-NMR of compound 20
Bn Cbz
OH N
TBSO
O
170
160
150
140
130
120
110
100
90
13
80
70
60
30
20
10
-10
O
Bn Cbz
O N
TBSO
O
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
-0.5
O
Bn Cbz
O N
TBSO
O
160
150
140
130
120
110
100
90
13
80
70
60
50
40
30
20
10
-10
O
Bn Cbz
O N
TBSO
OH
O
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
-0.5
O
Bn Cbz
O N
TBSO
OH
O
175
150
125
100
13
75
50
25
O
Bn Cbz
O N
HO
OH
O
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
-0.5
O
Bn Cbz
O N
HO
OH
O
160
150
140
130
120
110
100
13
90
80
70
60
50
40
30
20
10
-10
N
O
O
O
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
N
O
O
O
130
120
110
100
90
80
13
70
60
50
40
30
20
10
N
HO
OH
OH
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
-0.5
N
HO
OH
OH
110
100
90
80
70
13
60
50
40
30
20
TBSO
Cbz
NBn
HO
OH
O
7.5
7.0
6.5
6.0
5.5
5.0
4.5
TBSO
3.0
2.5
2.0
1.5
1.0
0.5
OH
O
150
3.5
Cbz
NBn
HO
175
4.0
125
100
13
75
50
25
0.0
TBSO
N
O
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
TB S O
N
O
140
130
120
110
100
90
80
13
70
60
50
40
30
20
10
-10
TBSO
NBn
HO
O
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
TBSO
NBn
HO
O
175
150
125
100
13
75
50
25
TBSO
BnN
HO
O
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
TBSO
BnN
HO
O
175
150
125
100
13
75
50
25
TBSO
N
O
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
TBSO
N
O
150
140
130
120
110
100
90
13
80
70
60
50
40
30
20
10
-10
HO
N
HO
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
HO
80
3.0
2.5
2.0
1.5
1.0
0.5
HO
90
OH
70
60
13
N
OH
50
40
30
20
10
HO
BnN
HO
O
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
HO
BnN
HO
O
160
150
140
130
120
110
13
100
90
80
70
60
50
40
30
N
O
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
N
O
200
175
150
125
13
100
75
50
25
TBSO
NBn
HO
O
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
TBSO
NBn
HO
O
170
160
150
140
130
120
110
100
13
90
80
70
60
50
40
30
20
10
-10
TBSO
BnN
HO
O
7.5
7.0
6.5
6.0
5.5
5.0
4.5
TBSO
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
10
-10
BnN
HO
O
150
140
130
120
110
100
90
13
80
70
60
50
40
30
20

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Eur. J. Org. Chem. 2013 WILEY-VCH Verlag GmbH & Co.

KGaA, 69451 Weinheim, 2013 ISSN 1434193X

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