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Concise and Effective Synthesis of 1→2 α-Linked Mannopyranosyl Oligosaccharides and Related Antigenic Factor 34 and Dominant of Antigenic Factor 13
Yu-Liang Zhu,
Fan-Zuo Kong,
Yu-Liang Zhu
Research Center for Eco- Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China
Search for more papers by this authorFan-Zuo Kong
Research Center for Eco- Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China
Search for more papers by this authorYu-Liang Zhu,
Fan-Zuo Kong,
Yu-Liang Zhu
Research Center for Eco- Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China
Search for more papers by this authorFan-Zuo Kong
Research Center for Eco- Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China
Search for more papers by this authorAbstract
A highly concise and effective synthesis of 1 → 2 α-linked mannopyranosyl oligosaccharides was achieved via TMSOTf promoted condensation of the corresponding benzoylated monosaccharide alkyl orthoester. 1→2 α-Linked mannosyl di, trisaccharide, antigenic factor 34, and dominant of antigenic factor 13 were readily synthesized by the new method.
References
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All new compounds gave satisfactory elemental analysis. Selected physical data and 1H NMR (400 MHz, CDCl3) data are as follows: For 4: m.p. 148–150°C, [α]
+ 3.0° (c 1.3, CHCl3); 1H NMR δ: 8.07–7.33 (m, 30H, ArH), 5.99 (t, J = 9.9 Hz, 1H), 5.90–5.85 (m, 4H), 5.70 (dd, J =1.7, 3.0 Hz, 1H, H-2′), 5.28–5.18 (m, 2H, CH2 = CHCH2), 5.16 (d, J=1.5 Hz, 1H), 5.11 (d, J = 1.7 Hz, 1H), 4.61–4.47 (m, 5H), 4.42–4.39 (m, 1H), 4.37 (dd, J=1.5, 2.9 Hz, 1H), 4.15–4.13 (m 1H), 3.95–3.92 (m, 1H), 2.03 (s, 3H, CH3CO). Anal. Calcd. for C59H52O18: C 67.56, H 4.96; Found: C 67.60, H4.92. For 16: m.p. 140–143°C, [α]
-8.4° (c 1.1, CHCl3); 1H NMR δ: 8. 14–7.25 (m, 65H, ArH), 6.35 (t, J= 10.0 Hz, 1H), 6.02 (t, J = 9.9Hz, 1H), 5.92–5.74 (m, 8H), 5.62 (dd, J = 9.9, 3.2 Hz, 1H), 5.58 (dd, J = 3.1, 1.5 Hz, 1H), 5.48 (d, 1H,), 5.30 (dd, 1H, CH2 = CHCH2), 5.27 (s, 1H), 5.22 (dd, 1H, CH2=CHCH2), 5.13 (d, J= 1.5 Hz, 1H), 5.10(s, 1H), 5.03 (s, 1H), 4.81–4.75 (m, 2H), 4.71 (dd, J = 3.1. 1.5 Hz, 1H), 4.60–4.40 (m, 8H), 4.47–4.42 (m. 2H), 4.27–4.15 (m, 4H), 3.93–3.85 (m. 2H), 3.82–3.78 (m. 1H), 2.52–3.48 (m, 1H). 2.22 (s, 3H. CH3CO), 2.06 (s, 3H. CH3CO), 2.04 (s, 3H. CH3CO). Anal. Calcd. for C130H114O42: C 66.50. H4.86; Found: C 66.55, H4.82. For 17: m.p. 136–139°C, [α]
−9.9°(c 1.2, CHCl3); 1H NMR δ: 8.00–7.25 (m. 60H. ArH), 6.15 (t, J = 9.8 Hz, 1H), 5.97 (t, J = 9.8 Hz. 1H). 5.90–5.82 (m, 6H), 5.79 (dd, J = 9.8, 3.0 Hz, 1H,), 5.70 (dd, J = 9.9, 3.1Hz, 1H), 5.65 (dd, J = 3.0, 1.5 Hz, 1H), 5.49 (dd, J = 3.0, 1.5 Hz, 1H), 5.36 (s, 1H), 5.32 (s, 1H), 5.26 (dd, J=17.2, 1.4 Hz, 1H, CH2 = CHCH2), 5.20 (s, 1H), 5.18 (dd, J = 10. 3, 1.4 Hz, 1H, CH2 = CHCH2), 5.08 (d, J= 1.6 Hz, 1H), 4.80 (s, 1H), 4.69–4.37 (m, 18H), 4.24 (dd, J = 3.0, 1.5 Hz, 1H), 4.17–4.12 (m, 1H), 3.79–3.75 (m, 1H), 2.14 (s, 3H, CH3CO), 1.99 (s,6H, 2CH3CO), 1.97 (s, 3H, CH3CO). Anal. Calcd. for C125H112O42: C 65.67, H 4.90; Found: C 65.64, H 4.93.
