E. Bourgeaux, J.-C. Combret / Tetrahedron: Asymmetry 11 (2000) 4189–4205
4203
0.84 (m, 3H), 1.30 (m, 4H), 1.52 (m, 3H), 2.01 (s, 3H), 2.83 (t, 1H, J 9.70), 2.94–3.98 (m), 4.46
(d, 1H, J 9.70), 5.39–5.57 (m, 7×1H), 7.22 (m, 3H), 7.43 (m, 2H); lC (CDCl3) 14.1, 21.8, 23.0,
28.8, 30.1, 59.3, 59.3, 59.3, 59.4, 59.6, 59.7, 59.7, 59.8, 60.1, 60.2, 60.3, 60.6, 60.8, 60.9, 61.1,
61.5, 69.6, 70.1, 70.3, 70.3, 70.6, 71.2, 71.2, 71.6, 71.7, 72.1, 72.4, 73.1, 73.9, 73.9, 74.1, 74.1,
79.5, 79.7, 80.6, 81.7, 81.7, 81.8, 82.6, 83.1, 83.2, 83.5, 87.1, 88.5, 96.6, 97.1, 128.8, 129.2, 132.2,
134.1, 170.0; wmax (neat)/cm−1 3065, 2910, 1729.
4.2.11.4. Phenyl O-(4-O-acetyl-2,3,6-tri-O-methyl-h-
D
-glucopyranosyl)-(14)-hexakis [O-(2,3,6-
-glucopyranose,
tri-O-methyl-h- -glucopyranosyl)-(14)]-3,6-di-O-methyl-2-O-pentyl-1-thio-i-
D
D
16d. The same method was applied to yield a colorless oil, 28%; TLC in solvent A: Rf 0.14.
Anal. C84H144O41S requires: C, 54.81, H, 7.88, S, 1.75; found: C, 54.75, H, 7.85, S, 1.71; lH
(CDCl3) 0.82 (m, 3H), 1.33 (m, 4H), 1.55 (m, 3H), 2.04 (s, 3H), 2.80 (t, 1H, J 9.70), 2.89–3.92
(m), 4.39 (d, 1H, J 9.70), 5.28–5.45 (m, 7×1H), 7.20 (m, 3H), 7.31 (m, 2H); lC (CDCl3) 14.1,
22.1, 23.1, 28.7, 30.1, 59.4, 59.4, 59.5, 59.5, 59.6, 59.7, 59.7, 59.8, 60.0, 60.2, 60.4, 60.6, 60.7,
60.9, 61.1, 61.4, 69.6, 70.2, 70.3, 70.4, 70.6, 71.2, 71.3, 71.6, 71.7, 72.1, 72.5, 73.2, 73.7, 73.9,
74.1, 74.2, 79.5, 79.8, 80.6, 81.7, 81.8, 81.8, 82.6, 83.1, 83.2, 83.4, 87.1, 88.6, 96.6, 97.1, 128.6,
129.2, 132.5, 134.1, 170.0; wmax (neat)/cm−1 3065, 2910, 1734.
4.2.11.5. Phenyl O-(4-O-acetyl-2,3,6-tri-O-methyl-h-
D
-glucopyranosyl)-(14)-hexakis [O-(2,3,6-
-glucopyranose,
tri-O-methyl-h- -glucopyranosyl)-(14)]-2-O-methyl-3,6-di-O-pentyl-1-thio-i-
D
D
16e. The same method as for compound 16a was applied to yield a colorless oil, 32%; TLC in
solvent A: Rf 0.17. Anal. C88H152O41S requires: C, 56.49, H, 8.18, S, 1.71; found: C, 56.52, H,
8.15; S, 1.78; lH (CDCl3) 0.83 (m, 6H), 1.33 (m, 8H), 1.54 (m, 4H), 2.04 (s, 3H), 2.85 (t, 1H, J
9.70), 2.90–4.05 (m), 4.48 (d, 1H, J 9.70), 5.36–5.48 (m, 7×1H), 7.12 (m, 3H), 7.34 (m, 2H); lC
(CDCl3) 14.5, 22.3, 23.2, 28.8, 30.2, 59.3, 59.3, 59.4, 59.5, 59.6, 59.7, 59.8, 59.8, 60.1, 60.1, 60.2,
60.4, 60.5, 60.9, 61.1, 61.3, 69.6, 70.1, 70.3, 70.8, 71.2, 71.2, 71.5, 71.7, 72.3, 72.5, 73.0, 73.8,
73.9, 74.0, 74.1, 79.6, 79.7, 80.6, 81.6, 81.8, 82.5, 83.2, 83.3, 83.5, 87.2, 88.6, 96.7, 97.3, 128.9,
129.1, 132.1, 134.0, 170.0; wmax (neat)/cm−1 3058, 2875, 1728.
4.2.11.6. Phenyl O-(4-O-acetyl-2,3,6-tri-O-methyl-h-
D
-glucopyranosyl)-(14)-hexakis [O-(2,3,6-
-glucopyranose,
tri-O-methyl-h- -glucopyranosyl)-(14)]-3-O-methyl-2,6-di-O-pentyl-1-thio-i-
D
D
16f. The same method as for compound 16a was applied to yield a colorless oil, 30%; TLC in
solvent A: Rf 0.17. Anal. C88H152O41S requires: C, 56.49, H, 8.18, S, 1.71; found: C, 56.45, H,
8.12; S, 1.70; lH (CDCl3) 0.82 (m, 6H), 1.34 (m, 8H), 1.56 (m, 4H), 2.06 (s, 3H), 2.87 (t, 1H, J
9.70), 2.85–4.08 (m), 4.49 (d, 1H, J 9.70), 5.35–5.50 (m, 7×1H), 7.12 (m, 3H), 7.35 (m, 2H); lC
(CDCl3) 14.4, 22.4, 23.3, 28.8, 30.3, 59.3, 59.4, 59.6, 59.7, 59.8, 59.9, 60.1, 60.2, 60.3, 60.3, 60.5,
60.7, 61.1, 61.3, 69.5, 70.1, 70.2, 70.6, 71.2, 71.3, 71.5, 71.8, 72.3, 72.4, 73.0, 73.8, 73.9, 74.1,
74.1, 79.6, 79.7, 80.5, 81.7, 81.9, 82.5, 83.1, 83.3, 83.4, 87.2, 88.7, 96.7, 97.4, 128.8, 129.1, 132.2,
134.1, 170.0; wmax (neat)/cm−1 3044, 2873, 1710.
4.2.12. General procedure for 17a–f
Note: Due to the very poor differences that appear for compounds 17a–f in comparison with
compounds 16a–f, characterizations of de-acetylated products 17a–f are not presented.