Synthetic studies of azido inositols and inositol based glycans 2

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NUS Appendix I: NMR Spectra of the Selected Compounds in Chapter 2 | 2012 National University of Singapore

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sandip | NON ee SS SACS ee F 1.30E+09 - 1.20E+09 - 1.10E+09 - 1.00E+09 S 44 /⁄ Ss Sos i - 9.00E+08 - 8.00E+08 F 7.00E+08 - 6.00E+08 Ne - 5.00E+08 - 4.00E+08 - 3.00E+08 | - 2.00E+08 | - 1.00E+08 - 0.00E+00 ae ry rẻ a tr m ` ah 8 S86 8 aa 8 L ể GnỦGG 6 SG 5 w -1.00E+08 T T T T T T T T T T T T T T T T T T T T T T T T 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 5 3.0 2.5 2.0 1.5 1.0 0.5 f1 (ppm) o- oo wonnoanonyt wo DOD h"wqooụk *** Current Data Parameters *** no qu0wee@se+ a cao RN oo

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BEI éẹ, of Singapore NUS National University Appendix I: NMR Spectra of the Selected Compounds in Chapter 2 | 2012 r 1.30E+09 Ƒ 1.20E+09 Ƒ 1.10E+09 | 1.00E+09 9.00E+08 [ 8.00E+08 | 7.00E+08 6.00E+08 - 5.00E+08 | 4.00E+08 | 3.00E+08 | 2.00E+08 Ƒ 1.00E+08 | 0.00E+00 Ƒ -1.00E+0ặ [ 6.5E+08 | 6.0E+08 [ 5.5E+08 - 5.0E+08 [ 4.5E+08 F 4.0E+08 [ 3.5E+08 | 3.0E+08 [ 2.5E+08 | 2.0E+08 [ 1.5E+08 | 1.0E+08 [ 5.0E+07 | 0.0E+00 - -5.0E+07

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SWANN meee Ne? | Đầu 00 Ộ ốểÝỹỹỶỲÝỲ 2-5 I l | W 4 1 FT" Ở ứ wn x N T T T T T T T T T T T T T 8.0 7.5 7.0 6.5 6.0 5.5 2.0 1.5 1.0 jan02sandip/2 5 8 13C Standard AC300 MLSP;21(6) Ở 88

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=1 NUS Appendix I: NMR Spectra of the Selected Compounds in Chapter 2 | 2012 National University of Singapore

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1HA đọ \g19/2Mlàp-22 See AO OG A SI? |_ a, Ộni F 1.10E+09 F 1.00E+09 F 9.00E+08 a Sf SO Ộ.Ềề Sf ~ Ss + 8.00E+08 (_ TT + 7.00E+08 F 6.00E+08 + 5.00E+08 + 4.00E+08 Ị F 3.00E+08 NS F 2.00E+08 Ị | | | | | | F 1.00E+08 II A + 0.00E+00 EỞTỞ+ m ET+ FỊ! TTIEI on N Nm T1 So TT Qo a6 o |" + F a 9 9S os S S a xỉ tư NN N aie bai ể Đ là | F- -1.00E+08 T T T T T T T T T T T T T T T T T T T T T T T T T T T 0 7.5 7.0 6.5 6.0 5.5 5.0 +5 ( fo 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm mh0107/3 3 3 5 F 8.0E+08

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National University of Singapore

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ANUS Appendix I: NMR Spectra of the Selected Compounds in Chapter 2 | 2012 National University of Singapore RYMRAGRARARASRANA a SS RN NS RRaASSBSRRRARSASS $F ầ Fe Fs ee ee SBRB SMA ded ed od od ũ N - 5.0E+08 tre ieee YP Pe - 4.5E+08 - 4.0E+08 it J Sf f J f Z ⁄ - 3.5E+08 [ 3.0E+08 > 2.5E+08 [ 2.0E+08 - 1.5E+08 | - 1.0E+08 lỊ 5.0E+07 lÌ | I + WA + 0.0E+00 đề lạng T | res tee 1 an AA Qo QOon 2 ồ a ae m(@ So omnNn lai ws lai I T T T T T T T T T T T T T T T T T T T T T T T 1.0 7.5 7.0 6.5 6.0 5.5 5.0 4 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 fl (ppm) eey1002/5 ou0 |

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=1 NUS Appendix I: NMR Spectra of the Selected Compounds in Chapter 2 | 2012

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=1 NUS Appendix 1: NMR Spectra of the Selected Compounds in Chapter 2 | 2012 National University of Singapore Sp230911/1 ẻ w Go tản Co =m mm m m cỦ m m em m om 1H AMX500 5-azido inositol MLSP-170 | = Kite S2 + 3.4E+08 F 3.2E+08 F 3.0E+08 2.8E+08 [ 2.6E+08 F 2.4E+08 > 2.2E+08 > 2.0E+08 - 1.8E+08 - 1.6E+08 - 1.4E+08 > 1.2E+08 - 1.0E+08 [ 8.0E+07 [ 6.0E+07 F 4.0E+07 [2.0E+07 1 Ở^ + 0.0E+00 ậ a Fe 8 N N a -2.0E+07 L T T T T T T T T T T T T T T T T T T T T T 7.5 7.0 6.5 6.0 5.5 5.0 4.0 5 3.0 2.5 2.0 1.5 1.0 0.5 fi (ppm) $p230911/2 8 8 8

13C AMX500 5-azido inositol MLSP-170 Sze

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sp0831/4 ` SSER Ậ$$S 3=5358Ọ0nnng 38 RKEERR00 0 0u G8 ự 8 tl 0 LẠ S8 ử ÊÌ 4 0E+08

1H AMXS500 MLỀP-86 wwrwvw wtwxwx xxvrvrmamặ7maựamãmmđự 6ự NN Ati nt det nt nA tA HAHAHAHAHA AAA HA

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sano904/1 ậ RAZR RRAARR BRVSR RBS ESSE EBRARRRERARAR 8.DE+08

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23 NUS National University of Singapore Appendix I: NMR Spectra of the Selected Compounds in Chapter 2 | 2012

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of Singapore NUS Appendix I: NMR Spectra of the Selected Compounds in Chapter 2 | 2012 National University | Integral | * 4H AMX500 MLSP-45

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\QUI1LL T1] T TRUCLIELILICL ILC 1 7 EXPNO : 1 Ỗ | TTT c | PROCNO : 1 *** Acquisition Parameters ** AQ mod : dqd AUNM j au_zg BF1 : 500.1300000 MHz BF2 :_ 800.1300000 MHz BF3 : 800.1300000 MHz DATEt : Ở 175105 DATEd : Apr162009 INSTRUM : av500 NS Ậ 3 O1 : 3088.51 Hz 02 : 3088.51 Hz 03 : 3088.51 Hz PARMODE : 1D SOLVENT : CDCI3 Sw : 20.6557 ppm | TE : 300.0 K | *** Processing Parameters *** | ; AZFW : 0.100 ppm LB : 0.30 Hz | MAXI : T0000.00 em MI : 0.00 cm | PC : 1.00 MỘC | Ở 1 Ở } Ở Ở ]} Ở Ww.: EM Ụ A | *** 1D NMR Plot Parameters ** 3 AQtime : 1.8859710 sec Ợ 43C AMX500 MLSP-45 oor a wee

ỷ R28 x bậP Qror ầ Current Data Parameters

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NUS National University Appendix I: NMR Spectra of the Selected Compounds in Chapter 2 | 2012 of Singapore 27Ợ HAMX600 MLSP+4 EEEHTT- 3 Ọ3 55:58 *** Current Data Parameters *** tán TT? 0 TT lun sp0418 + lO 1 Ị PROCNO 1 | ** Acquisition Parameters *** AQ_mod dqd AUNM au_zg BF1 : 500.1300000 MHz BF2 : 800.1300000 MHz BF3 : 800.1300000 MHz DATE_t 00:19:16 DATE_d Apr 18 2009 INSTRUM av500 NS 4 ử1 3088.51 Hz 02 3088.51 Hz O3 : 3088.51 Hz PARMODE : 1D SOLVENT : CDCI sw 20.6557 ppm TE 300.0 K ** Processing Parameters *** | AZFW 0.100 ppm LB 0.30 Hz i MAXI 10000.00 cm | | | MI 0.00 cm || | | | lÍ PC 100 seen li ll ol a EM 8 le | Ys / ** 1D NMR Plot Parameters ***

z li| ề 8 ậ | rio 3 =! AQ_time 1.5859710 sec

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