A method for synthesizing musk extract (2r, 5r)-musclide-a1
A synthetic method and technology for synthesizing musk, applied in the preparation of organic compounds, organic chemical methods, chemical instruments and methods, etc., can solve problems such as limitations, low content, lengthy reaction routes, etc.
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Embodiment 1
[0018] Synthesis of (2R,5S)-6-methyl-2-benzyloxy-6-hepten-3-yn-5-ol 3
[0019] Under argon protection, add cyclopropaneaminoalcohol chiral ligand L1 (70.2mg, 0.2mmol, 0.2equiv) into a 10mL Shrek tube, then add toluene (4mL) and (R)-3-benzyloxy-1 - Butyne 2 (480.6mg, 3.0mmol), stir well at room temperature. The mixture was cooled to 0° C., dimethyl zinc (2.5 mL, 1.2M solution in toluene, 1.5 mmol, 3 equiv) was slowly added dropwise, and stirring was continued at this temperature for 2 h. Then the temperature was lowered to -20°C, methacrolein 1 (70.1mg, 1.0mmol) was slowly added dropwise, and the reaction was stirred at -20°C for 48h. After the reaction was completed, the reaction was quenched by adding ice, and the aqueous phase was washed with Et 2 O (3×15 mL) was extracted, and the organic phases were combined. Dry over anhydrous sodium sulfate, concentrate under reduced pressure, and finally purify by silica gel column chromatography (n-hexane / ethyl acetate=5:1) to obtai...
Embodiment 2
[0021] Synthesis of (2R,5R)-6-methyl-2-benzyloxy-5-heptanol sulfate 4
[0022] At 0°C, the Pt 2 O (50.0mg, 0.22mmol) was added to a 25mL Shrek bottle, methanol (2mL) was added under a hydrogen atmosphere, compound 3 (506.0mg, 2.2mmol) was dissolved in methanol (10mL) and added to the reaction system, the reaction temperature rose to room temperature, The reaction was stirred for 8h. After the reaction was completed, it was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product of 6-methyl-2-benzyloxy-5-heptanol.
[0023] The above crude product was dissolved in THF (10 mL), sulfur trioxide pyridine complex (880.0 mg, 5.5 mmol) was added at 0°C, and the reaction was stirred at room temperature for 2 h. After the reaction was completed, the reaction mixture was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (dichloromethane / methanol=10:1) to obtain (2R,5R...
Embodiment 3
[0025] Synthesis of (2R,5R)-Musclide-A1
[0026] Under hydrogen atmosphere, Pd / C (20.0 mg) and methanol (1 mL) were added to a 25 mL Shrek tube, compound 4 (100.0 mg, 0.31 mmol) was dissolved in methanol (3 mL), the above mixture was added, and the reaction was stirred for 8 h. After the reaction was complete, the reaction mixture was filtered, concentrated under reduced pressure, and finally purified by silica gel column chromatography (dichloromethane / methanol=10:1) to obtain (2R,5R)-Musclide-A1 (57.0mg, yield 81%), It is white powder. [α] D 21 =–8.5 (c 0.5, CHCl 3 ). 1 H NMR (300MHz, CD 3 OD)δ4.19–4.13(m,1H),3.74–3.68(m,1H),2.13–2.01(m,1H),1.77–1.53(m,4H),1.15(d,J=6.2Hz,3H ),0.96(d,J=5.6Hz,3H),0.93(d,J=5.6Hz,3H). 13 C NMR (75MHz, CD 3 OD) δ83.8, 67.1, 34.2, 30.4, 26.1, 21.8, 16.6, 16.3. HRMS (APCI-TOF): calcd for C 8 h 17 o 5 S[M-H] - 225.0791, found 225.0790.
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