Technology Process of (2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-methoxymethoxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraenal
There total 13 articles about (2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-methoxymethoxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraenal which
guide to synthetic route it.
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synthetic route:
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(2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-methoxymethoxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol
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112505-73-4
(2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-methoxymethoxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraenal
- Guidance literature:
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With
Celite; sodium acetate; pyridinium chlorochromate;
In
dichloromethane;
for 1.16667h;
Yield given;
Ambient temperature;
DOI:10.1021/jo00240a032
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112505-73-4
(2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-methoxymethoxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraenal
- Guidance literature:
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Multi-step reaction with 10 steps
1: 1.) NaH / 1.) THF, RT, 10 min, 2.) RT, 30 min
2: 88 percent / i-Bu2AlH / diethyl ether; hexane / 0.33 h / -70 °C
3: 14.58 g / NBS, dimethyl sulfide / CH2Cl2 / 1 h
4: 84 percent / 0.58 h / 100 °C
5: t-BuOK / tetrahydrofuran / 0.75 h / -78 - -45 °C
6: aq. AcOH / tetrahydrofuran / 1.17 h / 60 - 65 °C
7: acetonitrile / 16 h / 80 - 85 °C
8: i-Pr2NEt / CH2Cl2
9: i-BuAlH / diethyl ether; hexane / 9 h / -70 °C
10: PCC, NaOAc, Celite / CH2Cl2 / 1.17 h / Ambient temperature
With
N-Bromosuccinimide; dimethylsulfide; Celite; potassium tert-butylate; sodium acetate; sodium hydride; diisobutylaluminium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo00240a032
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112505-73-4
(2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-methoxymethoxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraenal
- Guidance literature:
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Multi-step reaction with 7 steps
1: 1.) DMSO/oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, from -60 to -30 deg C, 28 min, 2.) RT, 30 min
2: t-BuOK / tetrahydrofuran / 0.75 h / -78 - -45 °C
3: aq. AcOH / tetrahydrofuran / 1.17 h / 60 - 65 °C
4: acetonitrile / 16 h / 80 - 85 °C
5: i-Pr2NEt / CH2Cl2
6: i-BuAlH / diethyl ether; hexane / 9 h / -70 °C
7: PCC, NaOAc, Celite / CH2Cl2 / 1.17 h / Ambient temperature
With
oxalyl dichloride; Celite; potassium tert-butylate; sodium acetate; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo00240a032
