Exercise plus Solution Quick overview
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1.52.02.53.03.54.0 ppm
1
H
6.03
0.99
0.98
1.03
3.02
1.01
1.00
Inte-
gral
2318.56
2315.12
1910.74
1903.98
1897.22
1890.45
1883.69
1876.93
1870.17
2054.60
2044.90
2035.25
2127.68
2124.25
2118.23
2114.79
Hz
2663.8 9
2653.99
Hz
722.16
717.93
715.45
711.11
Hz
O
HO
HO
OH
SH
CH
2
OH
Solvent: D
2
O
1
H NMR spectrum
recorded at 600.40 MHz
1.52.02.53.03.54.04.5
1
H
ppm
1.5
2.0
2.5
3.0
3.5
4.0
4.5
1
H
1
H/
1
H DQF-COCY
recorded at 600.40 MHz
One of the exchangeable protons of the sugar has been
substituted with an alkyl group. Which alkyl group is in which
position?
Determine the stereochemistry in positions 2, 3 und 4.
Assign all proton and carbon signals.
Name the spin systems.
Explain the multiplet structure at about 1.2 ppm.
3.4
3.6
3.8
4.0
4.2
4.4
1
H
3.43.63.84.04.24.4
1
H
ppm
1.2
1.4
1.6
1.8
2.0
2.4
2.6
2.8
3.0
3.2
1
H
1.21.41.61.82.02.42.62.83.03.2
1
H
ppm
1
H/
1
H DQF-COCY
ecorded at 600.40 MHz
1
H/
1
H DQF-COCY
recorded at 600.40 MHz
Parts of the COSY
25.74
37.95
63.66
71.44
72.42
76.62
81.41
87.70
25
30
35
40
45
50
60
65
70
75
80
85
13
C
1.52.02.53.03.54.04.5
1
H
ppm
1
H/
13
C HSQC
recorded at 600.40/150.98 MHz