Water → 4-(2,3,4,6-Tetra-O-acetyl-D-glucopyranosyloxy)-(E)-2-styryl-1,3-dioxolane
Reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[O:24]C1C=CC(C=O)=CC=1)(=[O:3])[CH3:2].[CH3:33][C:34]([CH3:37])([O-])[CH3:35].[K+].[Br-].[C:40]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)CC2OCCO2)[CH:45]=CC=C[CH:41]=1.[OH2:65].[CH2:66]1[CH2:70][O:69][CH2:68][CH2:67]1>>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[O:24][CH:66]1[CH2:70][O:69][CH:68](/[CH:67]=[CH:33]/[C:34]2[CH:37]=[CH:45][CH:40]=[CH:41][CH:35]=2)[O:65]1)(=[O:3])[CH3:2]Participants
6
Reactant 5
Product 1
Procedure
4-(2,3,4,6-Tetra-O-acetyl-D-glucopyranosyloxy)benzaldehyde 2 (3.4 g, 7.5 mmol) was dissolved in THF (75 mL), potassium tert-butoxide (0.84 g, 7.5 mmol) and (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide 3 (3.95 g, 9.2 mmol) was added portionwise. The reaction mixture was heated to reflux for 10 h. After completion of the reaction, the mixture was added water and extracted with CH2Cl2 (2×100 mL). Organic layers were combined, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to yield 4 (2.5 g, 64%) as a white powder.
Workup
- temperatureThe reaction mixture was heated
- temperatureto reflux for 10 h
- customAfter completion of the reaction
- extractionextracted with CH2Cl2 (2×100 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-d57ced31665c4afcae4894a594037122
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321795B2
Reaction notes
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