Technology Process of (2R,4S,5S,10S,11R,12S,15R)-2,12-Bis-benzyloxy-4,10-bis-(tert-butyl-dimethyl-silanyloxy)-15-(tert-butyl-diphenyl-silanyloxymethyl)-5,11-dimethyl-heptadecan-8-one
There total 32 articles about (2R,4S,5S,10S,11R,12S,15R)-2,12-Bis-benzyloxy-4,10-bis-(tert-butyl-dimethyl-silanyloxy)-15-(tert-butyl-diphenyl-silanyloxymethyl)-5,11-dimethyl-heptadecan-8-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 79 percent / TiCl4 / CH2Cl2 / 12 h / -78 °C
2.1: 2,6-lutidine
3.1: O3 / pyridine / methanol / -78 °C
3.2: Me2S / methanol / -78 - 25 °C
4.1: 1.16 g / NaBH4 / methanol / 0.5 h / 0 - 25 °C
5.1: 70 percent / (PhO)3PCH3I / dimethylformamide / 1.5 h / 0 °C
6.1: LDA / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C
6.2: HMPA / tetrahydrofuran; various solvent(s) / 48 h / 0 °C
7.1: 950 mg / SiO2 / ethyl acetate; various solvent(s) / 36 h
With
2,6-dimethylpyridine; sodium tetrahydroborate; methyltriphenoxyphosphonium iodide; silica gel; titanium tetrachloride; ozone; lithium diisopropyl amide;
pyridine;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo001767c
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: O3 / pyridine / methanol / -78 °C
1.2: 89 percent / Me2S / methanol / 12 h / -78 - 20 °C
2.1: 71 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C
3.1: 95 percent / 2,6-lutidine / CH2Cl2 / 6 h / 0 °C
4.1: OsO4; Me3NO; water / 2-methyl-propan-2-ol; tetrahydrofuran; toluene
4.2: 75 percent / Pb(OAc)4 / diethyl ether / 0.25 h
5.1: 880 mg / TMSCl / 15 h / 0 - 25 °C
6.1: LDA / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C
6.2: HMPA / tetrahydrofuran; various solvent(s) / 48 h / 0 °C
7.1: 950 mg / SiO2 / ethyl acetate; various solvent(s) / 36 h
With
2,6-dimethylpyridine; osmium(VIII) oxide; chloro-trimethyl-silane; trimethylamine-N-oxide; water; silica gel; titanium tetrachloride; ozone; lithium diisopropyl amide;
pyridine;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; tert-butyl alcohol;
DOI:10.1021/jo001767c
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 89 percent / TMSOTf / CH2Cl2 / 37 h / -78 - -55 °C
2.1: O3 / pyridine / methanol / -78 °C
2.2: 89 percent / Me2S / methanol / 12 h / -78 - 20 °C
3.1: 71 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C
4.1: 95 percent / 2,6-lutidine / CH2Cl2 / 6 h / 0 °C
5.1: OsO4; Me3NO; water / 2-methyl-propan-2-ol; tetrahydrofuran; toluene
5.2: 75 percent / Pb(OAc)4 / diethyl ether / 0.25 h
6.1: 880 mg / TMSCl / 15 h / 0 - 25 °C
7.1: LDA / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C
7.2: HMPA / tetrahydrofuran; various solvent(s) / 48 h / 0 °C
8.1: 950 mg / SiO2 / ethyl acetate; various solvent(s) / 36 h
With
2,6-dimethylpyridine; osmium(VIII) oxide; chloro-trimethyl-silane; trimethylamine-N-oxide; trimethylsilyl trifluoromethanesulfonate; water; silica gel; titanium tetrachloride; ozone; lithium diisopropyl amide;
pyridine;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; tert-butyl alcohol;
DOI:10.1021/jo001767c