Methanesulfonate → HCID 53682799, compound
Reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:27]([OH:28])[C@@H:26]([CH2:29][OH:30])[O:25][C@H:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[C@@H:10]1[O:31][C@H:32]1[O:61][C@H:60]([CH2:62][O:63][CH2:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[C@@H:51]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C@H:42]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C@H:33]1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:71]([O-])(=[O:74])(=[O:73])[CH3:72]>>[CH2:1]([O:8][C@H:9]1[C@H:27]([OH:28])[C@@H:26]([CH2:29][O:30][S:71]([CH3:72])(=[O:74])=[O:73])[O:25][C@H:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[C@@H:10]1[O:31][C@H:32]1[O:61][C@H:60]([CH2:62][O:63][CH2:64][C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)[C@@H:51]([O:52][CH2:53][C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)[C@H:42]([O:43][CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[C@H:33]1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
3
Procedure
Compound 38 (450 mg, 0.47 mmol) was converted into its 6-O-methane sulfonyl derivative exactly as described for the preparation of 10 to provide 39 (385 mg, 79.1%) as a syrup after chromatography on silica gel using (hexane:ethyl acetate; 2:1) as eluant; ›α!D +36.1° (c 0.95, chloroform). 1H-n.m.r. (CDCl3): δ 4.99(d, 1H, J1',2' 3.8 Hz, H-1'), 4.96(d, 1H, J1,2 3.8 Hz, H-1), 3.58(s, 3H, OCH3), 2.93(s, 3H, CH3SO2), 2.39(d, 1H, J 3.2 Hz, OH, D2O exchangeable), 2.21(t, 2H, J 7.5 Hz, CH2COO).
Sources & evidence
- ORD record
- ord-69e0b05bc65b4dea8936e1e77f7cf086
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05877157
Reaction notes
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