Technology Process of (3R,5R)-5-methyl-1-(phenylmethoxy)undec-6-yn-3-ol
There total 9 articles about (3R,5R)-5-methyl-1-(phenylmethoxy)undec-6-yn-3-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(S)-1,3-Bis-benzyloxy-5-methyl-undec-6-yn-5-ol;
With
dicobalt octacarbonyl;
In
dichloromethane;
at 20 ℃;
With
boron trifluoride diethyl etherate;
In
dichloromethane;
at -20 ℃;
With
ammonium cerium(IV) nitrate;
In
acetone;
at 0 ℃;
Further stages.;
DOI:10.1021/jo0055436
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 88 percent / Red-Al / tetrahydrofuran; toluene / 0 °C
2.1: POCl3 / CH2Cl2 / 4 h / 0 °C
3.1: NaH; Bu4NI / tetrahydrofuran / 24 h / 20 °C
4.1: 0.26 g / aq. HCl / methanol / 0.08 h / 20 °C
5.1: SO3-pyridine; Et3N / dimethylformamide; CH2Cl2 / 20 °C
6.1: tetrahydrofuran / -78 °C
7.1: 0.19 g / PCC; NaOAc / CH2Cl2 / 20 °C
8.1: hexane; tetrahydrofuran / -78 °C
9.1: Co2(CO)8 / CH2Cl2 / 20 °C
9.2: BF3*OEt2 / CH2Cl2 / -20 °C
9.3: 0.13 g / CAN / acetone / 0 °C
With
hydrogenchloride; dicobalt octacarbonyl; pyridine-SO3 complex; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; trichlorophosphate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
1.1: Ring cleavage / 2.1: Etherification / 3.1: Alkylation / 4.1: Hydrogenolysis / 5.1: Oxidation / 6.1: Grignard reaction / 7.1: Oxidation / 8.1: Substitution / 9.1: Metallation / 9.2: Reduction / 9.3: demetallation;
DOI:10.1021/jo0055436
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: POCl3 / CH2Cl2 / 4 h / 0 °C
2.1: NaH; Bu4NI / tetrahydrofuran / 24 h / 20 °C
3.1: 0.26 g / aq. HCl / methanol / 0.08 h / 20 °C
4.1: SO3-pyridine; Et3N / dimethylformamide; CH2Cl2 / 20 °C
5.1: tetrahydrofuran / -78 °C
6.1: 0.19 g / PCC; NaOAc / CH2Cl2 / 20 °C
7.1: hexane; tetrahydrofuran / -78 °C
8.1: Co2(CO)8 / CH2Cl2 / 20 °C
8.2: BF3*OEt2 / CH2Cl2 / -20 °C
8.3: 0.13 g / CAN / acetone / 0 °C
With
hydrogenchloride; dicobalt octacarbonyl; pyridine-SO3 complex; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; pyridinium chlorochromate; trichlorophosphate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
1.1: Etherification / 2.1: Alkylation / 3.1: Hydrogenolysis / 4.1: Oxidation / 5.1: Grignard reaction / 6.1: Oxidation / 7.1: Substitution / 8.1: Metallation / 8.2: Reduction / 8.3: demetallation;
DOI:10.1021/jo0055436
