Supporting Information III Efficient Convergent Synthesis of Bi-, Tri-, and Tetraantennary Complex Type N-Glycans and Their HIV-1 Antigenicity Sachin S Shivatare,,, Shih-Huang Chang,, Tsung-I Tsai, Chien-Tai Ren, Hong-Yang Chuang,, Li Hsu,, Chih-Wei Lin,, Shiou-Ting Li, Chung-Yi Wu,*,, and Chi-Huey Wong*, The supporting information contains 1 H, 13 C, and 2D NMR spectrum of compounds (S2-S55). S1
S2 1.0 2.5 3.0 3.5 4.0 5.0 5.5 1.3122 1.3249 1.4991 111 747 874 1.6002 1.9501 1.9823 1.9949 1.9987 2.8908 2.9033 2.9163 3.3455 3.3486 3.3609 3.4569 3.4613 3.4704 3.4852 3.5049 3.5079 3.5118 3.5222 3.5320 3.5397 3.5653 3.5768 3.5826 3.5907 3.5982 3.6186 3.6307 3.6495 3.6596 3.6628 3.6693 3.6825 3.6917 3.6947 3.7090 3.7113 3.7252 3.7447 3.7525 3.7736 3.7844 3.7962 3.8041 3.8230 3.8330 3.8433 3.8479 3.8629 3.8769 3.8895 3.9028 3.9202 4.1766 4.1948 4.2206 4.3619 4.3656 4.3744 4.6402 4.7253 4.7308 4.7765 2.36 2.40 4.42 7.44 9.45 0 2.35 5.16 64.99 6 4.01 1.64 2.15 2.57 0.84 4.2 4.4 4.6 4.8 5.0 6 4.01 1.64 2.15 2.57 0.84 2.5 2.36 2.40 4.42 7.44 9.45 0 2.35 H H H H H H H H H H H H H H NH 2 4 H H H H H H H H H H H H CH H H H H CH 24
24.81 24.88 25.41 25.45 29.00 29.09 30.77 41.78 47 42.38 42.80 54.18 54.63 57.71 57.90 62.83 63.04 64.32 65.40 65.69 66.01 66.10 67.63 70.08 70.77 70.93 71.14 71.29 72.81 73.48 73.57 74.45 78 74.81 74.89 75.17 75.31 76.42 76.86 77.09 77.23 77.35 78.82 78.93 79.12 79.44 81.77 82.15 83.14 99.54 102.91 102.99 103.05 103.14 103.55 103.79 104.11 106.11 106.27 176.20 176.25 177.15 177.46 177.54 177.71 H H CH H H H H H H H H H H H H H H CH H H H H H H H H H H H H H H 4 NH 2 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 S3
Compound 24 2.5 3.0 3.5 4.0 5.0 5.5 5.5 5.0 4.0 3.5 3.0 2.5 S4
Compound 24 20 30 40 50 60 70 80 90 100 110 5.5 5.0 4.0 3.5 3.0 2.5 S5
Compound 24- HMBC H3e g g' H3a g g' 20 30 40 50 60 70 80 90 100 110 120 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 1.9 1.8 1.7 1.6 1.4 1.3 S6
Compound 24- TCSY 0.5 1.0 2.5 3.0 3.5 4.0 5.0 5.5 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 S7
1.4190 1.4319 1.6062 1.6183 1.6303 1.6791 1.6919 1.7046 1.8266 1.8342 572 740 800 923 2.7763 2.9937 3.0064 3.0191 3.4312 3.4469 3.5797 3.5954 3.6164 3.6298 3.6385 3.6448 3.6516 3.6682 3.6877 3.7000 3.7099 3.7190 3.7274 3.7369 3.7517 3.7677 3.7811 3.7950 3.8097 3.8150 3.8309 3.8474 3.8579 3.8742 3.8902 3.9127 3.9322 3.9381 3.9653 3.9845 4.0056 4.0125 4.0288 4.1461 4.2600 4.2650 4.2933 4.2983 4.3214 616 685 746 815 4.7353 4.8419 4.8591 4.8739 5.0385 5.0524 H H H H CH H H H H H 5.4 5.2 5.0 4.8 4.6 4.4 3.0 2.8 2.6 2.4 2.2 1.8 1.6 H H H H H H H CH H H H H H H H H H H H H H H 4 NH2 7.5 7.0 6.5 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 0.5 1.11 1.30 1.82 1.18 1.99 3.81 57.58 3.73 1.81 1.71 7.30 8.07 1 2.31 1.78 0 S8
24.77 24.82 24.91 24.94 25.33 25.39 29.10 30.78 46 42.30 42.36 54.42 57.73 57.86 57.92 58.01 62.68 62.84 63.76 64.42 64.48 65.32 67.54 69.48 70.15 70.21 70.83 71.10 72.11 72.82 74.49 74.73 74.84 74.87 75.03 75.10 75.62 77.09 77.21 77.28 77.41 77.90 78.07 78.13 78.22 79.01 79.11 79.26 79.40 80.48 81.27 87 81.71 82.18 99.63 102.57 102.92 103.28 103.78 103.92 104.02 105.33 105.61 177.17 177.76 Compound 25 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 S9
Compound 25- CSY 2.5 3.0 3.5 4.0 5.0 5.5 6.0 6.0 5.5 5.0 4.0 3.5 3.0 2.5 S10
Compound 25- TCSY 2.5 3.0 3.5 4.0 5.0 5.5 5.5 5.0 4.0 3.5 3.0 2.5 S11
Compound 25- HSQC 20 30 40 50 60 70 80 90 100 110 6.0 5.5 5.0 4.0 3.5 3.0 2.5 S12
1.6918 1.7046 1.7234 1.7276 1.7446 531 559 594 717 784 835 983 2.1089 2.2493 2.9952 3.0080 3.0207 3.4558 3.5517 3.5659 3.5810 3.5958 3.6142 3.6298 3.6390 3.6435 3.6543 3.6659 3.6757 3.6868 3.6974 3.7061 3.7129 3.7181 3.7227 3.7274 3.7303 3.7358 3.7563 3.7622 3.7734 3.7854 3.7982 3.8013 3.8155 3.8216 3.8277 3.8350 3.8417 3.8487 3.8643 3.8722 3.8903 3.9012 3.9085 3.9118 3.9256 3.9537 3.9855 4.0004 4.0163 4.3092 4.3145 4.4638 4.4723 4.4797 4.6958 4.8431 4.8690 H H H H H H H H CH H H CH H H H H H H H H H H H H H H CH H H H H H H H H H H H H H H 4 NH 2 5.0 4.8 4.6 4.4 4.2 3.0 2.8 2.6 2.4 2.2 1.8 1.6 7.5 7.0 6.5 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 0.5 4.07 1.90 0.86 1.79 0.46 0.49 4.67 105.89 1.35 3.00 5.89 14.00 6.88 3.04 3.08 1.31 4 S13
21.99 25 22.12 22.34 22.49 22.65 22.71 26.32 28.01 30.20 39.30 40.04 40.11 40.15 51.87 54.84 54.92 60.06 60.18 60.26 62.44 62.58 62.63 63.29 65.08 67.42 67.76 68.16 68.20 68.25 68.36 70.04 70.42 70.72 70.87 71.68 71.74 71.87 71.95 72.14 72.35 72.39 72.55 72.64 73.62 74.40 74.49 79.31 100.19 100.20 100.25 100.32 100.39 100.98 101.05 101.33 103.30 103.41 103.46 173.45 173.51 174.33 174.39 H H H H H H H H CH H H CH H H H H H H H H H H H H H H CH H H H H H H H H H H H H H H 4 NH 2 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 S14
Compound 26 2.5 3.0 3.5 4.0 5.0 5.5 5.5 5.0 4.0 3.5 3.0 2.5 S15
Compound 26 20 30 40 50 60 70 80 90 100 110 5.5 5.0 4.0 3.5 3.0 2.5 S16
Compound 26 96 97 98 99 100 101 102 103 104 105 5.2 5.1 5.0 4.9 4.8 4.7 4.6 4.4 4.3 S17
976 1.6711 1.8089 279 297 446 653 671 709 2.7501 2.7576 2.7707 2.7783 2.9732 2.9858 2.9987 3.5645 3.5822 3.5950 3.6100 3.6221 3.6317 3.6350 3.6473 3.6484 3.6566 3.6682 3.6793 3.6975 3.7014 3.7076 3.7166 3.7320 3.7373 3.7412 3.7564 3.7620 3.7755 3.7826 3.7952 3.8404 3.8435 3.8560 3.8720 3.8812 3.8900 3.8975 3.9015 3.9065 3.9126 3.9166 3.9441 3.9500 3.9647 3.9814 3.9855 4.0007 4.0184 4.1145 4.1247 4.1303 4.2487 4.2818 511 581 636 711 4.6552 4.8511 H H H H H H H H CH CH H H H H H H H H H H H H H H H H CH H H H H H H H H H H H H H H 4 NH2 5.2 5.0 4.8 4.6 4.4 3.0 2.8 2.6 2.4 2.2 1.8 1.6 7.5 7.0 6.5 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 0.5 53.99 14.44 8.34 3.53 3.58 1.60 1.05 0.73 1.48 3.30 1.11 0.98 1.25 0.52 0.62 1.90 3.00 14.06 5.07 4 2.21 2.71 2.18 S18
176.62 177.05 177.16 177.55 177.73 29.10 30.77 46 42.36 54.41 57 57.72 57.80 57.92 58.08 62.73 62.82 63.77 64.48 65.31 70.21 70.55 70.83 71.11 72.11 72.81 74.49 79 74.66 74.84 74.98 75.11 75.24 75.61 77.12 77.24 77.37 77.69 77.89 78.19 79.08 79.38 81.08 81.31 89 102.55 102.60 103.28 103.79 103.87 104.00 104.12 105.30 105.37 105.54 Compound 27 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 S19
Compound 27 2.5 3.0 3.5 4.0 5.0 5.5 5.5 5.0 4.0 3.5 3.0 2.5 S20
Compound 27 20 30 40 50 60 70 80 90 100 110 6.0 5.5 5.0 4.0 3.5 3.0 2.5 S21
1.6865 1.7325 556 900 944 2.1274 2.6879 2.7008 2.9863 2.9973 2.9992 3.0118 3.5538 3.5573 3.5668 3.5698 3.5753 3.5783 3.5824 3.5907 3.5932 3.6060 3.6153 3.6233 3.6250 3.6558 3.6658 3.6720 3.6756 3.6841 3.6880 3.6961 3.6991 3.7049 3.7067 3.7127 3.7160 3.7187 3.7220 3.7272 3.7333 3.7361 3.7411 3.7440 3.7684 3.7733 3.7845 3.7999 3.8037 3.8106 3.8159 3.8330 3.8390 3.8494 3.8590 3.8684 3.8919 3.8973 3.9012 3.9059 3.9079 3.9123 3.9173 3.9213 3.9280 3.9488 3.9546 4.0172 4.6139 H H H H H H H H CH H H H CH H H H H H H H H H H H H H H H H 4 NH 2 5.0 4.8 4.6 4.4 4.2 3.0 2.8 2.6 2.4 2.2 1.8 1.6 7.5 7.0 6.5 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 0.5 0.62 1.46 0.96 2.15 1.46 43.60 2.24 1.64 5.43 3.73 1.88 0 3.23 1.93 S22
176.28 177.16 177.32 177.36 177.46 177.65 30.78 32.96 47 42.83 54.61 57.31 57.74 62.68 62.88 63.11 63.59 64.00 65.39 66.09 68.70 70.93 70.98 71.14 72.81 72.96 73.43 73.47 74.44 74.71 74.81 75.02 75.11 75.15 75.28 76.43 77.26 78.78 78.90 80.97 81.46 89 83.02 83.10 83.56 101.86 102.16 102.66 102.87 102.91 103.79 104.12 104.21 106.33 Compound 28 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 S23
Compound 28 2.5 3.0 3.5 4.0 5.0 5.5 5.5 5.0 4.0 3.5 3.0 2.5 S24
Compound 28 10 20 30 40 50 60 70 80 90 100 110 6.0 5.5 5.0 4.0 3.5 3.0 2.5 S25
H-1d Compound 28 99 100 J C,H = 159.8Hz 101 102 103 J C,H = 171.85Hz 104 105 106 107 J C,H = 160.6Hz 108 109 110 111 5.4 5.3 5.2 5.1 5.0 4.9 4.8 4.7 4.6 4.4 4.3 4.2 S26
Compound 28 J resolved S27
1.6159 1.6798 1.6925 1.7054 1.8259 535 571 691 893 970 2.9962 3.0092 3.0218 3.5825 3.5880 3.5906 3.5952 3.5987 3.6044 3.6119 3.6145 3.6233 3.6272 3.6300 3.6541 3.6679 3.6876 3.6925 3.6964 3.7115 3.7164 3.7201 3.7242 3.7289 3.7367 3.7430 3.7511 3.7576 3.7683 3.7820 3.7936 3.7966 3.8033 3.8178 3.8198 3.8596 3.8759 3.8823 3.8919 3.9016 3.9093 3.9117 3.9169 3.9205 3.9283 3.9313 3.9387 3.9818 3.9867 4.1310 4.1361 4.1475 4.1526 4.2196 617 749 4.6111 4.7920 5.1433 H H H H CH H H H H H H H H H H H H H H 4 NH 2 H H H CH H H H H H H 5.0 4.8 4.6 4.4 3.0 2.8 2.6 2.4 2.2 1.8 1.6 7.5 7.0 6.5 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 0.5 0.87 1.30 3.82 1.08 2.16 2.11 60.92 2.37 2.19 2.35 13.04 5.41 5 2.62 1 0 S28
24.77 24.83 24.87 24.89 25.13 29.09 30.78 45 42.36 54.41 57.55 57.73 57.89 62.69 62.79 62.84 63.57 63.75 64.03 65.31 68.69 70.03 70.20 70.83 71.10 71.29 72.10 72.82 72.96 73.04 70 74.67 74.87 75.11 75.61 77.26 77.54 77.89 78.07 78.16 78.19 78.77 78.90 80.70 80.97 81.04 81.46 86 82.97 101.81 102.33 102.53 102.55 102.67 103.79 104.13 104.28 105.31 176.61 176.63 177.16 177.29 177.32 177.40 177.74 Compound 29 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 S29
Compound 29 2.5 3.0 3.5 4.0 5.0 5.5 5.5 5.0 4.0 3.5 3.0 2.5 S30
Compound 29 20 30 40 50 60 70 80 90 100 110 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 S31
Compound 29 100.0 100.5 101.0 10 10 102.5 J C, H = 172.1Hz 103.0 J C, H = 158.9Hz 103.5 104.0 10 105.0 105.5 106.0 J C, H = 162.1Hz 106.5 107.0 107.5 5.4 5.3 5.2 5.1 5.0 4.9 4.8 4.7 4.6 4.4 4.3 S32
Compound 29 J Resolved S33
1.6170 1.6936 1.7065 1.7334 1.7468 576 922 959 2.1121 2.1286 2.6885 2.7017 2.7091 2.9976 3.0105 3.0231 3.5252 3.5664 3.5796 3.5948 3.6094 3.6263 3.6372 3.6481 3.6567 3.6665 3.6763 3.6851 3.6882 3.7004 3.7055 3.7190 3.7223 3.7362 3.7391 3.7435 3.7490 3.7727 3.7787 3.7844 3.7887 3.8021 3.8101 3.8178 3.8240 3.8346 3.8409 3.8510 3.8595 3.8777 3.8935 3.9020 3.9068 3.9132 3.9179 3.9283 3.9324 3.9380 3.9497 3.9555 3.9611 3.9997 4.0171 4.0352 4.2461 4.4618 4.4716 4.6204 4.6328 H H CH H H H H H H H H H H H H H H H CH H H H CH H H H H H H H H H H H H H H H H H H 4 NH 2 5.0 4.8 4.6 4.4 4.2 3.0 2.8 2.6 2.4 2.2 1.8 1.6 7.5 7.0 6.5 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 0.5 1.00 1.09 1.25 2.13 3.28 1.31 4.37 101.77 2.38 3.64 12.69 6.00 2.93 2.90 2.58 6.69 2.58 S34
24.78 24.82 24.87 24.99 25.02 25.15 25.23 29.09 30.77 46 42.81 54.62 57.32 57.39 57.61 57.67 57.73 62.67 62.85 62.89 62.95 65.39 66.05 70.87 70.95 71.14 72.80 72.87 73.43 73.47 74.45 74.71 74.82 74.89 75.02 75.11 75.15 75.28 76.42 77.03 77.09 77.16 77.26 78.95 87 82.32 83.12 83.34 83.53 99.72 100 102.15 102.87 102.91 103.79 104.12 104.20 106.31 176.28 177.15 177.35 177.39 177.45 177.47 Compound 30 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 S35
Compound 30 2.5 3.0 3.5 4.0 5.0 5.5 5.5 5.0 4.0 3.5 3.0 2.5 S36
Compound 30 20 30 40 50 60 70 80 90 100 110 6.0 5.5 5.0 4.0 3.5 3.0 2.5 S37
Compound 30 H-1d H-1d' 98 99 100 101 J C,H= 169.5Hz 102 103 J C,H= 172.4Hz 104 J C,H= 161.6Hz J C,H= 162.5Hz 105 106 107 J C,H= 162.2Hz 108 109 5.4 5.3 5.2 5.1 5.0 4.9 4.8 4.7 4.6 4.4 4.3 S38
Compound 30- HMBC 3 x H-3 equi. sialic acid 3 x H-3 axial sialic acid 20 30 40 50 60 70 80 90 100 110 120 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 1.9 1.8 1.7 1.6 1.4 1.3 1.2 1.1 S39
5.1399 4.9331 4.6261 4.6127 999 818 742 614 209 081 4.2333 4.1497 4.1347 4.0750 4.0558 4.0266 4.0071 3.9848 3.9524 3.9344 3.9183 3.9080 3.8893 3.8754 3.8589 3.8418 3.8318 3.8162 3.8007 3.7905 3.7795 3.7734 3.7585 3.7417 3.7298 3.7202 3.7096 3.6871 3.6674 3.6527 3.6278 3.6119 3.6032 3.5957 3.5818 3.5245 3.5091 3.0208 3.0081 2.9953 2.7889 2.7741 2.1348 2.1074 964 677 560 1.8464 1.8263 1.8065 1.7042 1.6914 1.6787 1.6269 1.6152 1.6029 1.4290 1.4199 1.4161 H H H H CH H H H H H H H H H H H H H H H H H H H H H 4 NH 2 H H H H H 5.0 4.8 4.6 4.4 3.0 2.8 2.6 2.4 2.2 1.8 1.6 7.5 7.0 6.5 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 0.5 1.28 2.25 7.44 1.35 2.26 4.48 87.84 1.92 2.93 7.39 16.80 3.00 2.33 2.14 6 H H H H CH H H H H CH S40
174.43 174.64 175.00 28.03 39.31 39.61 51.67 54.84 54.99 55.16 59.91 60.08 61.01 61.30 61.63 62.57 65.73 67.34 67.46 68.08 68.36 69.37 70.07 71.75 71.93 74 72.14 72.36 72.87 74.36 72 74.68 74.80 75.14 75.46 76.05 76.28 77.95 78.29 79.29 79.41 80.22 97.05 99.08 99.47 99.59 99.83 100.32 101.05 101.39 107 102.57 102.63 Compound 31 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 S41
Compound 31 2.5 3.0 3.5 4.0 5.0 5.5 5.5 5.0 4.0 3.5 3.0 2.5 S42
Compound 31 20 30 40 50 60 70 80 90 100 110 5.5 5.0 4.0 3.5 3.0 2.5 S43
1.4176 1.4305 925 1.6033 1.6154 1.6271 1.6652 1.6780 1.6907 1.7037 1.7163 1.7262 1.7334 1.7458 1.7659 553 596 903 973 2.1122 2.1280 2.3858 2.6801 2.6881 2.7011 2.7083 2.9936 3.0063 3.0191 3.4296 3.5497 3.5651 3.5778 3.5918 3.6004 3.6257 3.6553 3.6649 3.6748 3.6853 3.6992 3.7220 3.7394 3.7596 3.7881 3.8027 3.8132 3.8192 3.8306 3.8362 3.8481 3.8944 3.9153 3.9265 3.9540 4.0001 4.0155 4.0328 4.2432 4.2566 4.4571 4.4698 4.4878 096 222 918 4.6168 4.9227 5.1614 H H H H H H H H H H H H H H H CH H H CH H H H CH H H H H H CH H H H H H H H H H H H H H H H H H H H H H 5.2 5.0 4.8 4.6 4.4 4.2 4 NH2 3.0 2.8 2.6 2.4 2.2 1.8 1.6 7.5 7.0 6.5 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 0.5 S44
173.77 176.26 177.14 177.31 177.45 177.64 182.32 24.87 25.02 25.23 25.34 29.09 30.76 46 42.82 46.58 54.61 57.35 57.42 57.55 57.70 62.70 62.85 63.09 63.19 65.39 66.07 70.97 71.13 72.79 73.43 74.44 74.69 74.81 75.11 75.29 76.41 77.17 77.24 89 83.17 99.91 101.84 102.12 102.91 103.79 104.15 104.20 106.32 Compound 32 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 S45
Compound 32 2.5 3.0 3.5 4.0 5.0 5.5 5.5 5.0 4.0 3.5 3.0 2.5 S46
Compound 32 20 30 40 50 60 70 80 90 100 110 6.0 5.5 5.0 4.0 3.5 3.0 2.5 S47
Compound 32 H-1d H-1d' 99 100 J C,H = 170.4Hz J C,H = 159.75 Hz 101 102 103 J C,H = 172.3Hz 104 105 106 107 J C,H = 163.3Hz 108 109 110 5.4 5.3 5.2 5.1 5.0 4.9 4.8 4.7 4.6 4.4 4.3 4.2 4.1 S48
1.4011 1.4125 867 979 1.6094 1.6484 1.6612 1.6737 1.6861 1.6987 1.8171 383 458 886 2.7303 2.7674 2.9770 2.9894 3.0020 3.3476 3.4095 3.5073 3.5533 3.5976 3.6065 3.6512 3.6716 3.6936 3.7435 3.7582 3.8682 3.8921 3.9362 3.9793 3.9990 4.0489 4.1018 4.2176 4.4837 4.4929 035 623 961 4.6063 5.1359 H H H H H H H H H H H H H H H H H H 7.5 7.0 6.5 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 0.5 6.09 7.41 18.59 6.08 169.20 5 6 27.67 15.71 4.06 3.06 4.00 2.95 H H H H H H H H H H H H CH CH H H CH H H H H H 4 NH 2 H H H H CH H H H H H S49
44 42.34 54.40 57.60 57.69 57.83 62.55 62.81 63.76 64.02 65.33 70.21 70.83 71.12 71.27 72.11 72.79 73.68 74.49 74.66 74.88 75.09 75.21 75.61 77.11 77.25 77.41 77.54 77.88 78.06 78.18 80.81 81.01 83 103.78 104.18 104.33 105.35 105.61 Compound 33 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 S50
Compound 33 2.5 3.0 3.5 4.0 5.0 5.5 6.0 6.0 5.5 5.0 4.0 3.5 3.0 2.5 S51
Compound 33 30 40 50 60 70 80 90 100 110 6.0 5.5 5.0 4.0 3.5 3.0 2.5 S52
1.2615 1.2765 1.2875 1.6016 2.1638 2.1695 2.3379 3.5096 3.5268 3.6198 3.6406 3.6790 3.6925 4.0805 4.0865 4.0928 4.1121 4.1219 4.1761 4.1900 4.2253 4.3726 4.3928 4.4303 4.4503 4.4732 4.4825 039 809 4.6009 4.7382 4.8261 4.8469 5.2238 5.2376 5.2827 5.2866 5.4445 6.7472 6.7587 6.9089 6.9121 6.9245 6.9462 6.9496 6.9588 6.9849 6.9956 7.1515 7.1636 7.2243 7.2401 7.2741 7.2808 7.2877 7.2924 7.2998 7.3071 7.3258 7.3288 7.3377 7.3437 7.3465 7.3498 7.4167 7.4194 7.4280 7.4324 7.6484 Ph Ac Bn Bn H Bn Bn NPhth NPhth 4 N 3 5.8 5.6 5.4 5.2 5.0 4.8 4.6 4.4 4.2 4.0 3.8 3.6 3.4 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 9.50 21.90 8.24 3.38 7.94 5.73 1.16 1.01 3 1.03 1.06 1.02 1.00 2.24 1.11 1.10 1.06 1.15 1.28 2.26 6.06 3.47 4.89 2.42 1.00 1.06 1.02 3 1.03 1.01 1.16 5.73 7.94 6.06 2.26 1.11 1.10 1.06 1.15 1.28 S53
97.01 98.10 99.28 100.39 108 102.16 123.14 123.66 125.31 126.25 126.89 127.20 127.33 127.51 127.55 127.64 127.84 127.88 127.99 128.07 128.24 128.29 128.35 128.59 129.05 129.29 129.40 133.64 133.82 134.03 76.03 76.81 76.84 77.00 77.24 78.55 79.14 21.02 Ph Ac Bn Bn H Bn Bn NPhth NPhth 4 N 3 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 S54
Compound 10 1 2 3 4 5 6 7 8 9 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.0 3.5 3.0 2.5 1.0 0.5 S55