Synthetic studies of azido inositols and inositol based glycans 3

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Appendix 2: NMR Spectra of the selected Compounds in Chapter 3 2012

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Appendix 2: NMR Spectra of the selected Compounds in Chapter 3 2012

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=1 NUS Appendix 2: NMR Spectra of the selected Compounds in Chapter 3 | 2012 National University

of Singapore

sp170111/ as F

1H AMXSOG-MLSP-322 TS ii 30 28 26 19 18 16 09 08 00 98 89 88 87 78 78 76 51 + F2.00E+08 - 1.90E+08 — - 1.80E+08 - 1.70E+08 - 1.60E+08 / + 1.50E-+08 f (Sure 4 1 A0E+08 _ 1.30E+08 L 1.20E+08 - 1.10E+08 - 1.00E+08 - 9.00E+07 [ 8.00E+07 [ 7.00E+07 | 6.00E+07 - 5.00E+07 4.00E+07 | 3.00E+07 | 2,00E+07 1.00E+07 ˆ wl Le | 0.00E+00 k r -1.00E+0? Loy TT T7TTT T r 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 T T T T T T T T T T T T 10.5 100 95 9.0 8.5 8.0 75 7.0 6.5 0 5.5 5.0 fl (ppm) Sp170111/2 [ 5.5E+08 13C AMX500 MLSP-322 77.25 CDC3 77.00 CDCI3 76.75 CDCI3 — 192 — 152.42 128 128 127, 125 122 119 80.25 28.21 | 5.0E+08 ‹ [ 4.5E+08 | 4.0E+08 [ 3.5E+08 | 3.0E+08 [ 2.5E+08 | 2.0E+08 [ 1.5E+08 trị F 1.0E+08 [ 5.0E+07

wate i | 0.0E+00 5.0E+07

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 T T T T T T T T T T

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10

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SANUS Appendix 2: NMR Spectra of the selected Compounds in Chapter 3 | 2012 National University of Singapore

spPINSAANNASS SRB SSRaRess - Rà 0Ð (DO tÕ (Ð (O (Ð tD (D O (O 8 t+

Co Nee + 1.00E+09 + 9.00E+08 | | | ] Ị | + 8.00E+08 + 7.00E+08 Ss (Ồ + 6.00E+08 N L H + 5.00E+08 3-14 + 4.00E+08 + 3.00E+08 + 2.00E+08 + 1.00E+08 ow A A, + 0,00E+00 roe an a š hà $ amt Ao oxnon N T T T T T T T T T T T r T T T T T T T T T T T T T T T T T 3.0 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 fl (ppm) sp170311/2 5 3 8

13C AMX500 MLSP-334 ca minmugaota oy 4 q28@R83øägSä 8 AR 888 no g + 7.5E+08

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TANI LS Appendix 2: NMR Spectra of the selected Compounds in Chapter 3 National University of Singapore 2012 Sf — 5.09 —~ 4.83 ™ 4.78 LS” 1.60E+09 Ƒ 1.50E+09 | 1.40E+09 Ƒ 1.30E+09 Ƒ 1.20E+09 Ƒ 1.10E+09 Ƒ 1.00E+09 | 9.00E+08 | 8.00E+08 - 7.00E+08 6.00E+08 Ƒ 5.00E+08 | 4.00E+08 | 3.00E+08 | 2.00E+08 Ƒ 1.00E+08 | 0.00E+00 —— FT+T FTTIE—T—" Ñ ce ag es we g 8 N lai T T T T T T T T }.5 8.0 7.5 7.0 6.5 5.0

sp090711/1 RR AAAANR RRA A AREER TAS SS ese saagws NNN NO OOOO OD

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National University of Singapore

23 NUS

wy Appendix 2: NMR Spectra of the selected Compounds in Chapter 3 2012

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=1 NUS Appendix 2: NMR Spectra of the selected Compounds in Chapter 3 | 2012 National University of Singapore sp130711@ 1H AMXSO8 MLSP-404 5.21 5.20 5.19 3.36 3.34 2.53 2.52 2.51 h | 1.60E+08 < a < 1.50E+08 Ƒ 1.40E+08 T 1.30E+08 F 1.20E+08 —- NHBoc SJ Ss [+ 1.10E+08 F 1.00E+08 3-19 [ 9.00E+07 [ 8.00E+07 F 7.00E+07 [ 6.00E+07 | 5.00E+07 F 4.00E+07 | 3.00E+07 2.00E+07 | 1.00E+07 5 I 1 1 I ° Ƒ 0.00E+00 A | $ A 2 2.06 Š T -1.00E+07 45 110 105 100 95 90 85 80 75 70 65 50 45 40 35 3.0 nN J un 2.05] 6.0 5.5 f1 (ppm) sp130711/4 15C AMX500.MLSP-404 | 3.2E+08 —177 156.08 79.08 77.34 CDCI3 77.09 CDCI3 76.83 CDCI3 — 35.92 ™ 34.41 28.32 ‘ F 3.0E+08 F 2.8E+08 F 2.6E+08 F 2.4E+08 [ 2.2E+08

HO;C — NHBoc [ 2.0E+08

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SINUS National University

of Singapore

Appendix 2: NMR Spectra of the selected Compounds in Chapter 3 2012

spf8R 955 8 5 Họ E0 8 ae 9 a5 888 S§§4ã58Ns85ã5%8 ‡

1n xÙ “aly Bs 47 TNO 36 ưì Ưì Ln t+ mid NANNANN NNN SA h

HIAMSSÙÓ.MLSEUDD 2C] SQV) Vn \ `”? TS VN N O BocHN 3-20 | I I an — at | | 4 | , 4 | He qo ET— — == oe Em BB 8.8 8 § 5 8 a 4 x ti aod a ° a A a a g T T T 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 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 fl (ppm) sp130711/2 9 8 8

TSC AMESOO MESP-4I AAR ESHSRSITANG weer 8 RE 8

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2012

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=1 NUS Appendix 2: NMR Spectra of the selected Compounds in Chapter 3 | 2012 National University of Singapore ano L NR 1 RBRRSRRRRmmPRmmm=hn= LỆ LỆ LỘ LỘ LA An GAMMA AM NNNNNN SGA a Go it L

1H ANSXSD0U01 S012 a a4 ao (2 to] h2 Như [ 3.8E+08

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2012