Technology Process of methyl 1α-(benzyloxy)-8-bromo-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate
There total 14 articles about methyl 1α-(benzyloxy)-8-bromo-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 1.) MsCl, Et3N / 2.) Bu4NI / 1.) 0 deg C, 2.) DMF, 80 deg C
2: 1.) CH3COOH, CH3OH, 2.) NaIO4 / 1.) reflux 2.) THF, H2O
4: 67 percent / LDA / tetrahydrofuran / -78 - 23 °C
5: 1.) DIBAL-H / 1.) toluene, -78 deg C, 2.) CH2Cl2, RT
With
methanol; sodium periodate; diisobutylaluminium hydride; acetic acid; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide;
tetra-(n-butyl)ammonium iodide;
In
tetrahydrofuran;
DOI:10.1016/S0040-4039(00)98725-2
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 1.) BH3 2.) 3M NaOH, 30 percent H2O2 / 1.) THF, 0 deg C
2: 1.) MsCl, Et3N / 2.) Bu4NI / 1.) 0 deg C, 2.) DMF, 80 deg C
3: 1.) CH3COOH, CH3OH, 2.) NaIO4 / 1.) reflux 2.) THF, H2O
5: 67 percent / LDA / tetrahydrofuran / -78 - 23 °C
6: 1.) DIBAL-H / 1.) toluene, -78 deg C, 2.) CH2Cl2, RT
With
methanol; sodium hydroxide; sodium periodate; borane; dihydrogen peroxide; diisobutylaluminium hydride; acetic acid; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide;
tetra-(n-butyl)ammonium iodide;
In
tetrahydrofuran;
DOI:10.1016/S0040-4039(00)98725-2
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 2.) NaH / 1.) CH2Cl2, -78 deg C 2.) THF, DMF, reflux
2: 1.) BH3 2.) 3M NaOH, 30 percent H2O2 / 1.) THF, 0 deg C
3: 1.) MsCl, Et3N / 2.) Bu4NI / 1.) 0 deg C, 2.) DMF, 80 deg C
4: 1.) CH3COOH, CH3OH, 2.) NaIO4 / 1.) reflux 2.) THF, H2O
6: 67 percent / LDA / tetrahydrofuran / -78 - 23 °C
7: 1.) DIBAL-H / 1.) toluene, -78 deg C, 2.) CH2Cl2, RT
With
methanol; sodium hydroxide; sodium periodate; borane; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; acetic acid; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide;
tetra-(n-butyl)ammonium iodide;
In
tetrahydrofuran;
DOI:10.1016/S0040-4039(00)98725-2