RSC AdvancesRSC Advances 2 Facile synthesisSupporting of Urea-tethered Information and...

RSC Advances

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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: wdthb@163.com

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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

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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

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1H-1H COSY NMR Spectra of Compound 9a with partial enlarged detail in the glycosyl residue

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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

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1C-NMR spectra of Compound 11d in CDCl3

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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