Methanol → HCID 10668439, compound
Reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15][C@@H:16]2[O:33][C@H:32]([CH2:34][O:35]C(=O)C)[C@H:27]([O:28]C(=O)C)[C@H:22]([O:23]C(=O)C)[C@H:17]2[O:18][CH2:19][CH:20]=[CH2:21])[C@@H:8]([CH2:39][O:40]C(=O)C)[O:7][C@@H:6]1Cl)(=O)C.[CH3:45][OH:46]>>[CH2:19]([O:18][C@@H:17]1[C@@H:22]([OH:23])[C@@H:27]([OH:28])[C@@H:32]([CH2:34][OH:35])[O:33][C@H:16]1[O:15][C@@H:9]1[C@@H:8]([CH2:39][OH:40])[O:7][C@@H:6]([O:46][CH3:45])[C@H:5]([OH:4])[C@H:10]1[OH:11])[CH:20]=[CH2:21]Participants
3
Procedure
Chloride 3 (4.4 g, 6.74 mmol) was dissolved in dry MeOH and left at room temperature for two days. The mixture was neutralized with Dowex 50W (H+) resin, the suspension was filtered and the filtrate was crystallized from EtOH to give 4 (1.8 g, 67%), [α]D−1.8° (c 0.2, H2O), m.p. 22-223° C.; 1H NMR (D2O) δ 5.99 (m, 1H, Hc), 5.36 (m, 1H, Hb), 5.28 (m, 1H, Ha), 4.49 (d, 1H, J1′,2′=7.9 Hz, H-1′), 4.41 (d, 1H, J1,2=8.0 Hz, H-1), 4.34 (m, 1H, Hd), 4.26 (m, 1H, He), 3.99 (broad d, 1H, H-6a), 3.83-3.62 (m, 8H, H-3, H-4, H-5, H-6b, H-3′, H-5′, H-6′a, H-6′b), 3.58 (s, 3H, Me), 3.4dd, 1H, J2′,3′=10.0 Hz, H-2′), 3.32 (m, H-2). Calc'd for C16H28O11 (396.38) C, 48.48; H, 7.12. Found C, 48.47, H, 7.12.
Workup
- filtrationthe suspension was filtered
- customthe filtrate was crystallized from EtOH
Sources & evidence
- ORD record
- ord-42d6f813fafb42ea8eb0369786398184
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06310043B1
Reaction notes
Loading…