Technology Process of (3R,4S,5R,16S)-3,4,5-tris(benzyloxy)-1-(1,3-dioxolan-2-yl)heptadecane-2,16-diol
There total 14 articles about (3R,4S,5R,16S)-3,4,5-tris(benzyloxy)-1-(1,3-dioxolan-2-yl)heptadecane-2,16-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
for 5h;
Heating;
DOI:10.1021/ol0620287
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 9-BBN-H / tetrahydrofuran / 4 h / Heating
1.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 12 h / 20 °C
2.1: 92 percent / CBr4; Ph3P / CH2Cl2 / 24 h / 20 °C
3.1: Mg; dibromoethane / tetrahydrofuran / 4 h / Heating
3.2: CuBr*Me2S / tetrahydrofuran / 7 h / -25 - 20 °C
4.1: 89 percent / triflic acid / CH2Cl2; hexane / 48 h / 20 °C
5.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C
6.1: 89 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
7.1: 69 percent / SnCl4 / CH2Cl2 / 0.5 h / -78 °C
8.1: 99 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating
9.1: 79 percent / TBAI; NaH / tetrahydrofuran / 12 h / 0 °C
10.1: 69 percent / ZnCl2*OEt2 / CH2Cl2; diethyl ether / 72 h / Heating
11.1: O2 / CH2Cl2; methanol / 0.42 h / -78 °C
11.2: 88 percent / NaBH4 / CH2Cl2; methanol / -78 - 0 °C
12.1: 99 percent / TBAF / tetrahydrofuran / 5 h / Heating
With
lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; zinc chloride diethyl ether; 1,1-Dibromoethane; carbon tetrabromide; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; oxygen; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; magnesium; triphenylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
10.1: Sakurai reaction;
DOI:10.1021/ol0620287
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 92 percent / CBr4; Ph3P / CH2Cl2 / 24 h / 20 °C
2.1: Mg; dibromoethane / tetrahydrofuran / 4 h / Heating
2.2: CuBr*Me2S / tetrahydrofuran / 7 h / -25 - 20 °C
3.1: 89 percent / triflic acid / CH2Cl2; hexane / 48 h / 20 °C
4.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C
5.1: 89 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
6.1: 69 percent / SnCl4 / CH2Cl2 / 0.5 h / -78 °C
7.1: 99 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating
8.1: 79 percent / TBAI; NaH / tetrahydrofuran / 12 h / 0 °C
9.1: 69 percent / ZnCl2*OEt2 / CH2Cl2; diethyl ether / 72 h / Heating
10.1: O2 / CH2Cl2; methanol / 0.42 h / -78 °C
10.2: 88 percent / NaBH4 / CH2Cl2; methanol / -78 - 0 °C
11.1: 99 percent / TBAF / tetrahydrofuran / 5 h / Heating
With
lithium aluminium tetrahydride; zinc chloride diethyl ether; 1,1-Dibromoethane; carbon tetrabromide; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; oxygen; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; magnesium; triphenylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
9.1: Sakurai reaction;
DOI:10.1021/ol0620287
