Technology Process of (3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-5-hexen-3-ol
There total 4 articles about (3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-5-hexen-3-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(Z)-2-Butene;
With
(-)-B-methoxydiisopinocamphenylborane; n-butyllithium; potassium tert-butylate;
In
tetrahydrofuran; diethyl ether; hexane;
at -78 ℃;
for 0.5h;
3-<(3,4-Dimethoxyphenyl)methoxy>propanal;
With
boron trifluoride diethyl etherate;
In
tetrahydrofuran; diethyl ether; hexane;
at -78 ℃;
for 4h;
With
sodium perborate; water;
In
tetrahydrofuran; diethyl ether; hexane;
DOI:10.1139/v01-133
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: camphorsulfonic acid / benzene / 12 h / Heating
1.2: 37 percent / DIBAL-H / benzene; toluene / 1.08 h / 0 - 20 °C
2.1: 77 percent / DMSO; (COCl)2; Et3N / CH2Cl2 / 1.5 h / -78 °C
3.1: t-BuOK; n-BuLi; (-)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane; diethyl ether / 0.5 h / -78 °C
3.2: BF3*OEt2 / tetrahydrofuran; hexane; diethyl ether / 4 h / -78 °C
3.3: 72 percent / NaBO3*4H2O; H2O / tetrahydrofuran; hexane; diethyl ether
With
(-)-B-methoxydiisopinocamphenylborane; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene;
2.1: Swern oxidation;
DOI:10.1139/v01-133
- Guidance literature:
-
Multi-step reaction with 2 steps
1.1: 77 percent / DMSO; (COCl)2; Et3N / CH2Cl2 / 1.5 h / -78 °C
2.1: t-BuOK; n-BuLi; (-)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane; diethyl ether / 0.5 h / -78 °C
2.2: BF3*OEt2 / tetrahydrofuran; hexane; diethyl ether / 4 h / -78 °C
2.3: 72 percent / NaBO3*4H2O; H2O / tetrahydrofuran; hexane; diethyl ether
With
(-)-B-methoxydiisopinocamphenylborane; n-butyllithium; oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane;
1.1: Swern oxidation;
DOI:10.1139/v01-133
