Technology Process of (2R,3S,5R)-3-(2-Benzyloxy-ethyl)-5-methoxy-2-phenethyl-tetrahydro-furan
There total 8 articles about (2R,3S,5R)-3-(2-Benzyloxy-ethyl)-5-methoxy-2-phenethyl-tetrahydro-furan which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 7 steps
1: 1.) lead tetraacetate; 2.) K2CO3 / 1.) CH2Cl2, 22 deg C, 2 h; 2.) CH2Cl2, 1 h
2: tetrahydrofuran / 13 h / 22 °C
3: H2 / Pd/C / methanol / 1500.1 Torr
4: 1.) p-toluenesulfonic acid; 2.) lithium aluminum hydride / 1.) methanol-water, 8 h; 2.) THF, reflux, 1 h
5: 90 percent / sodium hydride / dimethylformamide / 4 h / 22 °C
6: 73 percent / p-toluenesulfonic acid / methanol / 24 h / 22 °C
7: 1.) NaH; 2.) CS2; 3.) methyl iodide; 4.) Bu3SnH / 4.) AIBN
With
lead(IV) acetate; carbon disulfide; lithium aluminium tetrahydride; hydrogen; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; methyl iodide;
palladium on activated charcoal; 2,2'-azobis(isobutyronitrile);
In
tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00222a024
- Guidance literature:
-
Multi-step reaction with 8 steps
1: AcOH/water / 37 h / 22 °C
2: 1.) lead tetraacetate; 2.) K2CO3 / 1.) CH2Cl2, 22 deg C, 2 h; 2.) CH2Cl2, 1 h
3: tetrahydrofuran / 13 h / 22 °C
4: H2 / Pd/C / methanol / 1500.1 Torr
5: 1.) p-toluenesulfonic acid; 2.) lithium aluminum hydride / 1.) methanol-water, 8 h; 2.) THF, reflux, 1 h
6: 90 percent / sodium hydride / dimethylformamide / 4 h / 22 °C
7: 73 percent / p-toluenesulfonic acid / methanol / 24 h / 22 °C
8: 1.) NaH; 2.) CS2; 3.) methyl iodide; 4.) Bu3SnH / 4.) AIBN
With
lead(IV) acetate; carbon disulfide; lithium aluminium tetrahydride; water; hydrogen; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; methyl iodide;
palladium on activated charcoal; 2,2'-azobis(isobutyronitrile);
In
tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00222a024
- Guidance literature:
-
Multi-step reaction with 6 steps
1: tetrahydrofuran / 13 h / 22 °C
2: H2 / Pd/C / methanol / 1500.1 Torr
3: 1.) p-toluenesulfonic acid; 2.) lithium aluminum hydride / 1.) methanol-water, 8 h; 2.) THF, reflux, 1 h
4: 90 percent / sodium hydride / dimethylformamide / 4 h / 22 °C
5: 73 percent / p-toluenesulfonic acid / methanol / 24 h / 22 °C
6: 1.) NaH; 2.) CS2; 3.) methyl iodide; 4.) Bu3SnH / 4.) AIBN
With
carbon disulfide; lithium aluminium tetrahydride; hydrogen; tri-n-butyl-tin hydride; sodium hydride; toluene-4-sulfonic acid; methyl iodide;
palladium on activated charcoal; 2,2'-azobis(isobutyronitrile);
In
tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00222a024
