RSC Advances
1
RSC AdvancesSUPPORTING INFORMATION
Supporting Information
For DOI:
This journal is © The Royal Society of Chemistry 2015
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2015
RSC Advances
2
Supporting Information
Facile synthesis of Urea-tethered and Thiocarbamate-
tethered Glycosyl beta-Amino Acids
Hanbing Teng*a,b, Zengwei Zhanga, Yifan Zhoua, Zhiyong Chena, Qi Chena,
Yang Liua, Wenjin Xua
E-mail: [email protected]
RSC Advances
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ContentsIR Spectroscopic Data .....................................................................................................................5
IR spectra of Compound 6 .........................................................................................................5IR spectra of Compound 7 .........................................................................................................5IR spectra of Compound 9a .......................................................................................................6IR spectra of Compound 9b .......................................................................................................6IR spectra of Compound 9c .......................................................................................................7IR spectra of Compound 9d .......................................................................................................7IR spectra of Compound 9e .......................................................................................................8IR spectra of Compound 11a .....................................................................................................9IR spectra of Compound 11b .....................................................................................................9IR spectra of Compound 11c ...................................................................................................10IR spectra of Compound 11d ...................................................................................................10
1H and 13C Spectroscopic Data .....................................................................................................111H-NMR spectra of Compound 9a in CDCl3...........................................................................1113C-NMR spectra of Compound 9a in CDCl3..........................................................................121H-1H COSY NMR spectra of Compound 9a in CDCl3..........................................................131H-1H COSY NMR Spectra of Compound 9a with partial enlarged detail in the glycosyl residue ......................................................................................................................................141H-13C COSY NMR Spectra of Compound 9a with partial enlarged detail in the glycosyl residue ......................................................................................................................................151H-NMR spectra of crude reaction mixture of Compound 9a in CDCl3 .................................161H-NMR spectra of Compound 9b in CDCl3 ..........................................................................171C-NMR spectra of Compound 9b in CDCl3...........................................................................181H-NMR spectra of Compound 9c in CDCl3 ...........................................................................1913C-NMR spectra of Compound 9c in CDCl3..........................................................................201H-NMR spectra of Compound 9d in CDCl3 ..........................................................................2113C-NMR spectra of Compound 9d in CDCl3 .........................................................................221H-NMR spectra of Compound 9e in CDCl3 ...........................................................................2313C-NMR spectra of Compound 9e in CDCl3..........................................................................241H-NMR spectra of Compound 11a in CDCl3.........................................................................2513C-NMR spectra of Compound 11a in CDCl3........................................................................261H-NMR spectra of Compound 11b in CDCl3 ........................................................................2713C-NMR spectra of Compound 11b in CDCl3 .......................................................................281H-NMR spectra of Compound 11c in CDCl3 .........................................................................2913C-NMR spectra of Compound 11c in CDCl3........................................................................301H-NMR spectra of Compound 11d in CDCl3 ........................................................................311C-NMR spectra of Compound 11d in CDCl3.........................................................................32
MS Spectroscopic Data..................................................................................................................33MS spectra of Compound 6 .....................................................................................................34MS spectra of Compound 9a ...................................................................................................34MS spectra of Compound 9b ...................................................................................................34MS spectra of Compound 9c....................................................................................................34
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MS spectra of Compound 9d ...................................................................................................34MS spectra of Compound 9e....................................................................................................35MS spectra of Compound 11a .................................................................................................35MS spectra of Compound 11b .................................................................................................35MS spectra of Compound 11c..................................................................................................35MS spectra of Compound 11d .................................................................................................36
RSC Advances
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IR Spectroscopic Data
IR spectra of Compound 6
IR spectra of Compound 7
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IR spectra of Compound 9a
IR spectra of Compound 9b
MeOOCNCO
NHBoc
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IR spectra of Compound 9c
IR spectra of Compound 9d
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IR spectra of Compound 9e
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IR spectra of Compound 11a
IR spectra of Compound 11b
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IR spectra of Compound 11c
IR spectra of Compound 11d
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1H and 13C Spectroscopic Data
1H-NMR spectra of Compound 9a in CDCl3
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13C-NMR spectra of Compound 9a in CDCl3
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1H-1H COSY NMR spectra of Compound 9a in CDCl3
RSC Advances
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1H-1H COSY NMR Spectra of Compound 9a with partial enlarged detail in the glycosyl residue
RSC Advances
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1H-13C COSY NMR Spectra of Compound 9a with partial enlarged detail in the glycosyl residue
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1H-NMR spectra of crude reaction mixture of Compound 9a in CDCl3
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1H-NMR spectra of Compound 9b in CDCl3
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1C-NMR spectra of Compound 9b in CDCl3
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1H-NMR spectra of Compound 9c in CDCl3
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13C-NMR spectra of Compound 9c in CDCl3
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1H-NMR spectra of Compound 9d in CDCl3
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13C-NMR spectra of Compound 9d in CDCl3
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1H-NMR spectra of Compound 9e in CDCl3
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13C-NMR spectra of Compound 9e in CDCl3
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1H-NMR spectra of Compound 11a in CDCl3
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13C-NMR spectra of Compound 11a in CDCl3
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1H-NMR spectra of Compound 11b in CDCl3
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13C-NMR spectra of Compound 11b in CDCl3
HN COOMe
NHBoc
S
O
O
OAcAcO
OAcOAc
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1H-NMR spectra of Compound 11c in CDCl3
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13C-NMR spectra of Compound 11c in CDCl3
SO
OAcAcO
OAcO
OAcAcO
OAc
AcO
OHN COOMe
NHBocO
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1H-NMR spectra of Compound 11d in CDCl3
RSC Advances
32
1C-NMR spectra of Compound 11d in CDCl3
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33
MS Spectroscopic Data
MS spectra of Compound 6
295.1010
299.12161+
310.1111
+MS, 0.1min #3
0
1
2
3
4
5
5x10Intens.
285 290 295 300 305 310 m/z
MS spectra of Compound 9a
475.18091+
614.25361+
906.8668
1205.49711+
1796.7458
+MS, 0.1min #4
0.0
0.5
1.0
1.5
2.0
6x10Intens.
500 1000 1500 2000 2500 m/z
MS spectra of Compound 9b
614.24641+
1205.4955
+MS, 0.1min #8
0
2
4
6
4x10Intens.
500 1000 1500 2000 2500 m/z
MS spectra of Compound 9c
475.18021+
614.25271+
1205.49721+
1796.74491+
2389.0007
+MS, 0.1min #6
0.0
0.5
1.0
1.5
2.0
6x10Intens.
500 1000 1500 2000 2500 m/z
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MS spectra of Compound 9d
475.18091+
614.24961+
902.34291+
1205.49671+
1493.5912
+MS, 0.3min #15
0.0
0.5
1.0
1.5
6x10Intens.
500 1000 1500 2000 2500 m/z
MS spectra of Compound 9e
327.17541+
485.24721+
902.34231+
+MS, 0.2min #10
0.0
0.2
0.4
0.6
0.8
6x10Intens.
500 1000 1500 2000 2500 m/z
MS spectra of Compound 11a
245.13441+
631.17641+
853.32171+
1239.36281+
+MS, 0.1min #4
0
1
2
3
45x10
Intens.
500 1000 1500 2000 2500 m/z
MS spectra of Compound 11b
245.13411+
631.17561+
1239.36021+
+MS, 0.1min #6
0
1
2
3
4
5x10Intens.
500 1000 1500 2000 2500 m/z
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MS spectra of Compound 11c
245.13421+
485.21911+
919.25851+ +MS, 0.1min #6
0
1
2
35x10
Intens.
500 1000 1500 2000 2500 m/z
MS spectra of Compound 11d
919.26811+
1815.5315
+MS, 0.1min #8
0.0
0.5
1.0
1.56x10
Intens.
500 1000 1500 2000 2500 m/z