Technology Process of (1E,3S,4R,6E)-8-(tert-butyldiphenylsilyloxy)-1-iodo-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene
There total 9 articles about (1E,3S,4R,6E)-8-(tert-butyldiphenylsilyloxy)-1-iodo-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-6-octen-1-yne;
With
tetrakis(triphenylphosphine) palladium(0); tri-n-butyl-tin hydride;
In
tetrahydrofuran;
at 0 ℃;
for 1h;
With
iodine;
In
dichloromethane;
at -78 - -25 ℃;
for 1h;
DOI:10.1021/ja048320w
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: DIBAL-H / CH2Cl2; toluene / 0.75 h / -78 °C
2.1: Amberlyst 15 / aq. methanol / 12 h / 50 °C
3.1: 18.9 g / TsOH*H2O / dimethylformamide / 17 h / 50 °C
4.1: 15.6 g / DIBAL-H / CH2Cl2; toluene / 4.5 h / -78 °C
5.1: 73 percent / Et3N; DMAP / CH2Cl2 / 2 h / -78 - -20 °C
6.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C
7.1: 12.2 g / PPh3 / CH2Cl2 / 1 h / -78 °C
8.1: 93 percent / t-BuOK / 2-methyl-propan-2-ol / 15 h
9.1: Pd(PPh3)4; Bu3SnH / tetrahydrofuran / 1 h / 0 °C
9.2: 62 percent / I2 / CH2Cl2 / 1 h / -78 - -25 °C
With
dmap; tetrakis(triphenylphosphine) palladium(0); Amberlyst 15; potassium tert-butylate; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
6.1: Dess-Martin oxidation / 7.1: Corey-Fuchs reaction;
DOI:10.1021/ja048320w
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: Amberlyst 15 / aq. methanol / 12 h / 50 °C
2.1: 18.9 g / TsOH*H2O / dimethylformamide / 17 h / 50 °C
3.1: 15.6 g / DIBAL-H / CH2Cl2; toluene / 4.5 h / -78 °C
4.1: 73 percent / Et3N; DMAP / CH2Cl2 / 2 h / -78 - -20 °C
5.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C
6.1: 12.2 g / PPh3 / CH2Cl2 / 1 h / -78 °C
7.1: 93 percent / t-BuOK / 2-methyl-propan-2-ol / 15 h
8.1: Pd(PPh3)4; Bu3SnH / tetrahydrofuran / 1 h / 0 °C
8.2: 62 percent / I2 / CH2Cl2 / 1 h / -78 - -25 °C
With
dmap; tetrakis(triphenylphosphine) palladium(0); Amberlyst 15; potassium tert-butylate; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
5.1: Dess-Martin oxidation / 6.1: Corey-Fuchs reaction;
DOI:10.1021/ja048320w
![(3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-6-octen-1-yne](/Databaselist/images/loading.webp)
