((3AS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanone
((3AS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanone Basic information
- Product Name:
- ((3AS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanone
- Synonyms:
-
- D-xylo-Pentodialdo-5,2-furanose, 4,5-O-(1-Methylethylidene)-1-C-4-Morpholinyl-,(5S)-
- ((3aS,5R,6S,6aS)-6-hydroxy-2,2-diMethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(Morpholino)Methanone
- (3aS,5R,6S,6aS)-[6-hydroxy-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-5-yl]-(morpholino)methanone
- LX-4211 int
- (5S)-4,5-O-(1-Methylethylidene)-1-C-4-morpholinyl-D-xylo-pentodialdo-5,2-furanose
- LX-4211 inermediate
- EOS-61383
- SOTA-005
- CAS:
- 1103738-19-7
- MF:
- C12H19NO6
- MW:
- 273.28
- Mol File:
- 1103738-19-7.mol
((3AS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanone Chemical Properties
- Boiling point:
- 479.3±45.0 °C(Predicted)
- Density
- 1.318±0.06 g/cm3(Predicted)
- pka
- 12.78±0.60(Predicted)
((3AS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanone Usage And Synthesis
Synthesis
To a solution of (3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylic acid (5.0 g, 24.5 mmol) in THF (100 ML, 20.x.) was added TBTU (11.8 g, 1.5 equiv), N-methylmorpholine (NMM, 4.1 mL, 1.5 equiv) and the mixture was stirred at 20° C. for 30 min. Morpholine (3.2 mL, 1.5 equiv) was added, and the reaction mixture was stirred at 20° C. for an additional 6h. The solid was filtered off by filtration, and the cake was washed with THF (10 mL, 2.x. .x.2). The organic solution was concentrated under a vacuum. The residue was purified by silica gel column chromatography (hexanes: EtOAc, from 1:4 to 4: 1) to afford 4.3 g of the desired morpholine amide (((3AS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanone) as a white solid.
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