Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO
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Supporting Information
© Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006
1
A Facile Method for Oxidation of Primary Alcohols to Carboxylic Acids and Its Application in
Glycosaminoglycan Syntheses
Lijun Huang, Nardos Teumelsan, Xuefei Huang*
Department of Chemistry, The University of Toledo, 2801 W. Bancroft Street, MS 602, Toledo, OH 43606, USA
Corresponding author: Tel: 1-419-530-1507; Fax: 1-419-530-4033;
Email: xuefei.huang@utoledo.edu
2
1H- and 13C- NMR Spectra
OH
O
4
1H-NMR (600 MHz, CDCl3)
3
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
4
250 200 150 100 50 0
OH
O
4
13C-NMR (100 MHz, CDCl3)
5
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
OH
O
MeO 6
1H-NMR (600 MHz, CDCl3)
6
OH
O
MeO 6
13C-NMR (100 MHz, CDCl3)
250 200 150 100 50 0
7
8
OH
4O 8
1H-NMR (400 MHz, CDCl3)
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
9
OH
4O 8
13C-NMR (100 MHz, CDCl3)
10
250 200 150 100 50 0
11
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
OOH
O O
O
O
O
10
1H-NMR (600 MHz, CDCl3)
12
13
250 200 150 100 50 0
OOH
O O
O
O
O
10
13C-NMR (100 MHz, CDCl3)
14
OOH
OBzSTol
BzOBzO
O
12
1H-NMR (400 MHz, CDCl3)
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
15
250 200 150 100 50 0
OOH
OBzSTol
BzOBzO
O
12
13C-NMR (100 MHz, CDCl3)
16
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
OOH
NPhthSTol
BnOPMBO
O
14
1H-NMR (400 MHz, CDCl3)
17
OOH
NPhth
STolBnOPMBO
O
14
13C-NMR (100 MHz, CDCl3)
250 200 150 100 50 0
18
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
OO
NPhth
BnOPMBO
O
1H-NMR (400 MHz, CDCl3)
15
19
20
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
OHO
NPhthSTol
BnOTBSO
17
O
1H-NMR (600 MHz, CDCl3)
21
OHO
NPhthSTol
BnOTBSO
17
O
13C-NMR (150 MHz, CDCl3)
250 200 150 100 50 0
22
OHO OBz
O
BzOBzO
O
19
23
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
24
O
HO OBz
O
BzOBzO
O
19
13C-NMR (100 MHz, CDCl3)
25
250 200 150 100 50 0
26
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
1H-NMR (600 MHz, CDCl3)
OOBn
NPhthOMe
HOBnO
O
21
27
13C-NMR (150 MHz, CDCl3)
OOBn
NPhthOMe
HOBnO
O
21
200 150 100 50 0
28
29
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
NPhth
OMeOBnO
1H-NMR (400 MHz, CDCl3)
BnO O
O
NPhth
OMeHOBnO
O
22
30
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
OHO OMe
O O
O
24
1H-NMR (600 MHz, CDCl3)
31
OHO OMe
O O
O
24
13C-NMR (150 MHz, CDCl3)
32
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
O
OBz
OBnO
BnOO
O
NPhthOMe
OPh
26
HO O
1H-NMR (400 MHz, CDCl3)
33
34
O
OBz
OBnO
BnOO
O
NPhthOMe
OPh
26
HO O
13C-NMR (100 MHz, CDCl3)
35
250 200 150 100 50 0
36
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
37
O
OBz
OTBSOBnO
OO
NPhth
OPhO
OBz
OOBnO
OO
NPhth
OMeOPhBnO O BnO O
29
1H-NMR (600 MHz, CD2Cl2)
38
O
OBz
OTBSOBnO
OO
NPhth
OPhO
OBz
OOBnO
OO
NPhth
OMeOPhBnO O BnO O
29
13C-NMR (100 MHz, CD2Cl2)
39
250 200 150 100 50 0
40
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
O
OBz
OTBSOBnO
OO
NPhth
OPhO
OBz
OOBnO
OO
NPhth
OPhBnO O BnO O
30
O
OBz
OOBnO
OO
NPhth
OMeOPh
BnO O
1H-NMR (600 MHz, CD2Cl2)
41
250 200 150 100 50 0
O
OBz
OTBSOBnO
OO
NPhth
OPhO
OBz
OOBnO
OO
NPhth
OPhBnO O BnO O
30
O
OBz
OOBnO
OO
NPhth
OMeOPhBnO O
13C-NMR (100 MHz, CD2Cl2)
42
43
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
O
OBz
OTBSOBnO
O
O
NPhth
O
O
OBn
OMeO
BnO
Ph
32
BnO O BnO O
1H-NMR (600 MHz, CDCl3)
44
45
O
OBz
OTBSOBnO
O
O
NPhth
O
O
OBn
OMeOBnO
Ph
32
BnO O BnO O
13C-NMR (150 MHz, CDCl3)
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10 -20
46
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
O
OBz BnOTBSO
BnO OOBn
N3
O
O
OBnOMeO
BnO34
1H-NMR (600 MHz, CDCl3)
BnO O
BnO O
47
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
O
OBz BnOTBSO
BnO OOBn
N3
O
O
OBnOMeO
BnO34
13C-NMR (150 MHz, CDCl3)
BnO O
BnO O
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