Triphenylphosphine → HCID 15108965, compound
Reaction equation
[C@@H:1]12[O:11][CH2:10][C@@H:8]([O:9]1)[C:6](O)=[C:4](O)[C@@H:2]2[OH:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([O:42][CH3:43])[CH:41]=1)[C:36](O)=[O:37].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:43][O:42][C:40]1[CH:39]=[C:35]([CH:34]=[C:33]([O:32][CH3:31])[CH:41]=1)[C:36]([O:3][C@@H:2]1[CH:4]=[CH:6][C@H:8]2[CH2:10][O:11][C@@H:1]1[O:9]2)=[O:37]Participants
Procedure
1.28 g (10.0 mmol) of 1,6-anhydro-β-D-threo-hex-3-enopyranose, 5.25 g (20.0 mmol) of triphenyl phosphine, and 3.64 g (20.0 mmol) of 3,5-dimethoxybenzoic acid were added to 16 ml of dry THF, and a solution obtained by dissolving 3.48 g (20.0 mmol) of diethylazodicarboxylate in 16 ml of dry THF was gradually dropped in the above mixture in a nitrogen-sealed ice-water bath. The resultant solution was stirred at room temperature for 45 hours. The solvent was distilled from the reaction solution at a reduced pressure. Triphenyl phosphine oxide as a byproduct was eliminated from the residue using a silica gel column (eluent: chloroform). The solvent was distilled from the resultant eluate at a reduced pressure, and the residue was purified using a silica gel column (hexane:ethyl acetate=5:1) to obtain 2.45 g (yield: 83.7%) of 1,6-anhydro-3,4-dideoxy-2-O-(3,5-dimethoxybenzoyl)-β-D-erythro-hex-3-enopyranose. This product was recrystallized from a solvent mixture of hexane and diethyl ether.
Workup
- customa solution obtained
- additionwas gradually dropped in the above mixture in a nitrogen-
- customsealed ice-water bath
- distillationThe solvent was distilled from the reaction solution at a reduced pressure
- distillationThe solvent was distilled from the resultant eluate at a reduced pressure
- customthe residue was purified
Sources & evidence
- ORD record
- ord-1390bf6950a34454b962458a1e725f5b
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05457192
Reaction notes
Loading…