Technology Process of Toluene-4-sulfonic acid (E)-(2S,6R)-2-[(2S,3S,4S,6R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-6-methyl-heptyl]-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester
There total 25 articles about Toluene-4-sulfonic acid (E)-(2S,6R)-2-[(2S,3S,4S,6R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-6-methyl-heptyl]-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 15 steps
2: AcOH / tetrahydrofuran; H2O / 50 °C
3: imidazole / dimethylformamide
4: 90 percent / t-BuOOH / (+)-DIPT, Ti(i-PrO)4 / CH2Cl2 / -20 °C
5: NaH / tetrahydrofuran / 0 °C
6: n-Bu4NF / tetrahydrofuran
7: Dess-Martin periodinane reagent
8: tetrahydrofuran
9: H2 / Pd/C / ethyl acetate
10: 1.) NaOH / 2.) CSA / 1.) EtOH, reflux; 2.) CH2Cl2
11: boron trifluoride etherate / 0 °C
12: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 °C
13: 93 percent / LiAlH4 / tetrahydrofuran / -20 °C
14: Et3N / DMAP / CH2Cl2
15: 2,6-lutidine / CH2Cl2
With
1H-imidazole; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine;
2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; palladium on activated charcoal; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate;
In
tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)70631-9
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 1.) (c-C5H9)2OTf, i-Pr2NEt / 2.) CH2Cl2, -78 deg C
2: 92 percent / DDQ / CH2Cl2
3: 1.) LiOH, H2O2; 2.) LiAlH4 / 1.) THF, H2O; 2.) THF, 0 deg C
4: (ClCO)2, Et3N / dimethylsulfoxide; CH2Cl2 / -78 °C
5: tetrahydrofuran
7: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 °C
8: 93 percent / LiAlH4 / tetrahydrofuran / -20 °C
9: Et3N / DMAP / CH2Cl2
10: 2,6-lutidine / CH2Cl2
With
lithium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; (c-C5H9)2OTf; dihydrogen peroxide; sodium hexamethyldisilazane; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
2,6-dimethylpyridine; dmap;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/S0040-4039(00)70631-9
- Guidance literature:
-
Multi-step reaction with 15 steps
2: AcOH / tetrahydrofuran; H2O / 50 °C
3: imidazole / dimethylformamide
4: 90 percent / t-BuOOH / (+)-DIPT, Ti(i-PrO)4 / CH2Cl2 / -20 °C
5: NaH / tetrahydrofuran / 0 °C
6: n-Bu4NF / tetrahydrofuran
7: Dess-Martin periodinane reagent
8: tetrahydrofuran
9: H2 / Pd/C / ethyl acetate
10: 1.) NaOH / 2.) CSA / 1.) EtOH, reflux; 2.) CH2Cl2
11: boron trifluoride etherate / 0 °C
12: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 °C
13: 93 percent / LiAlH4 / tetrahydrofuran / -20 °C
14: Et3N / DMAP / CH2Cl2
15: 2,6-lutidine / CH2Cl2
With
1H-imidazole; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine;
2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; palladium on activated charcoal; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate;
In
tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)70631-9
