Technology Process of (3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enal
There total 22 articles about (3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enal which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
pyridine-SO3 complex; triethylamine;
In
dichloromethane; dimethyl sulfoxide;
at 20 ℃;
for 1h;
DOI:10.1021/jo026743f
- Guidance literature:
-
Multi-step reaction with 8 steps
1: Cl2(PCy3)2Ru=CHPh / tetrahydrofuran / 20 °C
2: 84 percent / HCl gas / CH2Cl2 / 0.5 h / -10 °C
3: Et3N; pyr*SO3 / CH2Cl2; dimethylsulfoxide / 2 h / 0 - 5 °C
4: 81 percent / Et3N; LiCl / tetrahydrofuran / 15 h / 0 °C
5: 94 percent / NaBH4; CeCl3*7H2O / ethanol / 0.17 h / -78 °C
6: iPr2NEt; TBAI / dimethylformamide / 16 h / 20 °C
7: 4.17 g / TsOH / methanol / 0.5 h / 20 °C
8: 98 percent / SO3*pyridine; Et3N / dimethylsulfoxide; CH2Cl2 / 1 h / 20 °C
With
hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; pyridine-SO3 complex; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride;
Grubbs catalyst first generation;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
3: Parikh-Doering oxidation / 8: Parikh-Doering oxidation;
DOI:10.1021/jo026743f
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: t-BuOK / tetrahydrofuran / 1 h / 20 - 45 °C
1.2: 92 percent / tetrahydrofuran / 1.5 h / 20 °C
2.1: Cl2(PCy3)2Ru=CHPh / tetrahydrofuran / 20 °C
3.1: 84 percent / HCl gas / CH2Cl2 / 0.5 h / -10 °C
4.1: Et3N; pyr*SO3 / CH2Cl2; dimethylsulfoxide / 2 h / 0 - 5 °C
5.1: 81 percent / Et3N; LiCl / tetrahydrofuran / 15 h / 0 °C
6.1: 94 percent / NaBH4; CeCl3*7H2O / ethanol / 0.17 h / -78 °C
7.1: iPr2NEt; TBAI / dimethylformamide / 16 h / 20 °C
8.1: 4.17 g / TsOH / methanol / 0.5 h / 20 °C
9.1: 98 percent / SO3*pyridine; Et3N / dimethylsulfoxide; CH2Cl2 / 1 h / 20 °C
With
hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; pyridine-SO3 complex; potassium tert-butylate; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride;
Grubbs catalyst first generation;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
4.1: Parikh-Doering oxidation / 9.1: Parikh-Doering oxidation;
DOI:10.1021/jo026743f
![(3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol](/Databaselist/images/loading.webp)
