4-Fluorophenyl sulfinate → 5-[(4-fluorophenyl)sulfonyl]-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside
Reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[CH2:16][S:15][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12](I)[CH:13]=1)(=[O:3])[CH3:2].[F:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([O-:36])=[O:35])=[CH:30][CH:29]=1>>[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[CH2:16][S:15][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([S:34]([C:31]2[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=2)(=[O:36])=[O:35])[CH:13]=1)(=[O:3])[CH3:2]Participants
3
Procedure
By following a procedure analogous to Example 139 starting from 5-iodo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 4-fluorophenyl sulfinate, 5-[(4-fluorophenyl)sulfonyl]-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside is obtained in the form of a white solid (yield=24%).
Sources & evidence
- ORD record
- ord-d3edd9506b7a429e8958baee4a65c988
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148407B2
Reaction notes
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