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- The spectral data (300 MHz NMR, MS, IR) obtained for all new compounds corroborate the proposed structures 5a, m.p. 88–90 °C (hygroscopic). 1H NMR (D2O) δ 5.03 (d, J=3.8 Hz, 1H, H1′), 4.4 (m, 1H, H1, 3.9 (m, 1H), 3.5–3.9 (m, 8H), 3.44 (t, J=10.0 Hz, 1H, H7), 3.4 (m, 1H, H5β), 3.1 (m, 1H, H3β), 2.3 (m, 2H, H2β & H3α), 2.1 (m, 2H, H8a & H5α), 1.7 (m, 1H, H2α). 13C NMR (D,2O) δ 98.9, 79.8, 77.6, 75.7, 74.6, 74.2, 74.0, 72.4, 72.3, 71.7, 63.2, 54.9, 54.4, 35.4. MS (CI, CH4) m/z (rel. intensity) 352 (MH+, 16), 190 (30), 172 (100). 5b, m.p. 207–209 °C. 1H NMR (D2O) δ 5.35 (d, J=3.9 Hz, 1H, H1′), 4.4 (m, 1H, H1), 3.5–3.9 (m, 8H), 3.31 (t, J=9.4 Hz, 1H, H7), 3.2 (m, 1H, H5β), 3.1 (m, 1H, H3β), 2.3 (m, 2H, H2β & H3α), 2.2 (m, 1H, H8a), 2.06 (t, J=103 Hz, 1H, H5α), 1.7 (m, 1H, H2α). 13C NMR (D2O) δ 103.6, 82.5, 81.1, 76.4, 76.0, 75.2, 73.5, 73.3, 73.2, 72.9, 63.9, 58.5, 54.9, 36.1. MS (CI, CH4) m/z (rel. intensity) 352 (MH,+, 84), 334 (14), 190 (100), 172 (40), 154 (20), 136 (12). 5c, m.p. 205–207 °C. 1H NMR (D2O) δ 4.69 (d, J=7.8 Hz, 1H, H1′), 4.4 (m, 1H, H1), 3.9 (m, 1H), 3.6–3.9 (m, 4H), 3.4–3.5 (m, 4H), 3.31 (t, J=9.4 Hz, 1H, H7), 3.2 (m, 1H, H5β), 3.1 (m, 1H, H3β), 2.1–2.4 (m, 3H), 2.06 (t, J=10.3 Hz, 1H, H5α), 1.7 (m, 1H, H2α)- 13c NMR (D2O)δ 105.9, 82.3, 80.9, 79.5, 79.1, 76.9, 73.7, 73.4, 73.0, 72.9, 64.1, 58.6, 55.0, 36.2. MS (Cl, CH4) m/z (rel. intensity) 352 (MH+ 55), 334 (8), 190 (100), 172 (100), 163 (10), 154 (72), 145 (40), 136 (25). 5d, m.p. 205–207 °C 1H NMR (D2O)δ 5.36 (d, J=3.9 Hz, 1H, H1′), 4.4 (m, 1H, H,1), 3.5–3.9 (m, 8H), 3.41 (t, J=10.0 Hz, 1H, H7), 3.2 (m, 1H, H5β), 3.1 (m, 1H, H3β), 2.1-2.4 (m, 3H, H2β, H3α & H8a), 2.06 (t, J=11.2 Hz, 1H, H5α), 1.7 (m, 1H, H2α). 13C NMR (D2O)δ 102.8, 81.7, 80.2, 75.7, M 75.2, 74.4, 72.7, 72.5, 72.4, 72.1, 63.1, 57.7, 54.1, 35.3. MS (CI, CH4) m/z (rel. intensity) 352 (MH+, 100), 334 (10), 190 (35), 172 (12). 5e, m.p. 198–200 °C 1H NMR (D2O) δ 4.70 (d, J=8.1 Hz, 1H, H1′), 4.5, (m, 1H, H1′), 3.9 (m, 1H), 3.6–3.8 (m, 3H), 3.4–3.5 (m, 4H), 3.30 (t, J=10.0 Hz, 1H, H7), 3.0–3.2 (m, 2H, H5,β & H3β), 2.1–2.4 (m, 3H), 2.06 (t, J=112 Hz, 1H, H5α), 1.7 (m, 1H, H2α). 13C NMR (D2O) δ 105.2, 81.6, 80.1, 78.7, 78.4, 76.1, 72.9, 72.6, 72.2, 72.1, 63.3, 57.8, 54.2, 35.4. MS (CI, CH4) m/z (rel. intensity) 352 (MH+, 15), 334 (5), 190 (40), 172 (100). 5f, m.p. 120–123 °C (hygroscopic). 1H NMR (D2O)° 5.02 (d, J=3.6 Hz, 1H, H1′), 4.5 (m, 1H, H1), 3.6–3.9 (m, 6H), 3.6 (m, 1H), 3.3–3.5 (m, 4H), 2.7 (m, 2H), 2.42 (t, J=11.2 Hz, 1H, H5α), 2.2 (m, 1H), 2.1 (m, 1H). 13C NMR (D2O)δ 96.7, 81.2, 76.0, 74.7, 74.1, 74.0, 72.8, 72.0, 71.7, 70.4, 63.0, 56.9, 54.1, 30.7. MS (CI, CH,4) m/z (rel. intensity) 352 (MH+, 12) 190 (100) 172 (10), 154 (18), 136 (30)
- 1,8-Di-O-acetyl-7-O-benzoylcastanospermine (6a) was prepared from 7-O-benzoyl-6-O-carbobenzyloxy-l,8-cyclohexylidenylcastanospermine,12in 3 steps
- Liu , P. S. , Hoekstra , W. J. and King , C-H. R. 1990 . Tetrahedron Lett , 31 : 2829