Technology Process of (2R,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol
There total 10 articles about (2R,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(3R,4S,6R)-2,6-dimethyl-3-hydroxy-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene;
With
borane-THF;
In
tetrahydrofuran;
at -5 ℃;
for 2.25h;
With
sodium hydroxide; dihydrogen peroxide;
In
tetrahydrofuran; methanol;
at 0 - 20 ℃;
for 2h;
DOI:10.1021/jo034870l
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 91 percent / proton sponge / CH2Cl2 / 8 h / 20 °C
2.1: 89 percent / methanol; tetrahydrofuran / 2.5 h / 0 °C
3.1: 95 percent / ceric ammonium nitrate (CAN); H2O / acetonitrile / 0.5 h / 0 °C
4.1: 99 percent / imidazole / dimethylformamide / 18 h / 20 °C
5.1: 90 percent / DIBAL-H / CH2Cl2; toluene / 3 h / -78 °C
6.1: 80 percent / CH2Cl2 / 2.5 h / -78 °C
7.1: 97 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
8.1: NaHMDS / diethyl ether / 1 h / 0 - 20 °C
8.2: 98 percent / diethyl ether / 2 h / 20 °C
9.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 °C
10.1: BH3*THF / tetrahydrofuran / 2.25 h / -5 °C
10.2: 16 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran; methanol / 2 h / 0 - 20 °C
With
1H-imidazole; borane-THF; Proton Sponge; ammonium cerium(IV) nitrate; hydrogen fluoride; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
8.2: Wittig reaction;
DOI:10.1021/jo034870l
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 80 percent / CH2Cl2 / 2.5 h / -78 °C
2.1: 97 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
3.1: NaHMDS / diethyl ether / 1 h / 0 - 20 °C
3.2: 98 percent / diethyl ether / 2 h / 20 °C
4.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 °C
5.1: BH3*THF / tetrahydrofuran / 2.25 h / -5 °C
5.2: 16 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran; methanol / 2 h / 0 - 20 °C
With
borane-THF; hydrogen fluoride; sodium hexamethyldisilazane; Dess-Martin periodane;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
3.2: Wittig reaction;
DOI:10.1021/jo034870l
