Technology Process of Acetic acid (4S,5R)-1-{(R)-(tert-butyl-dimethyl-silanyloxy)-[(2R,3R,4R,5S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl]-methyl}-9-(4-methoxy-benzyloxy)-4-methyl-3-oxo-5-triethylsilanyloxy-nonyl ester
There total 14 articles about Acetic acid (4S,5R)-1-{(R)-(tert-butyl-dimethyl-silanyloxy)-[(2R,3R,4R,5S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl]-methyl}-9-(4-methoxy-benzyloxy)-4-methyl-3-oxo-5-triethylsilanyloxy-nonyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
2.1: DIBAL-H / CH2Cl2 / 0.5 h / -78 °C
3.1: 1.74 g / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 20 °C
4.1: (i-Pr)2NLi / tetrahydrofuran; hexane / 0.25 h / -78 °C
4.2: tetrahydrofuran; hexane / 0.25 h / -78 °C
5.1: 1.05 g / DMAP; pyridine / 0.67 h / 0 °C
With
pyridine; 2,6-dimethylpyridine; dmap; diisobutylaluminium hydride; Dess-Martin periodane; lithium diisopropyl amide;
In
tetrahydrofuran; hexane; dichloromethane;
1.1: Substitution / 2.1: Reduction / 3.1: Oxidation / 4.1: Metallation / 4.2: Addition / 5.1: Acetylation;
DOI:10.1021/jo991642b
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 58 percent / NaH; Bu4NI / tetrahydrofuran / 0 - 45 °C
2.1: 82 percent / PCC / CH2Cl2 / 3 h / 20 °C
3.1: Bu2BOTf; Et3N / CH2Cl2 / 0.75 h / 0 °C
3.2: 68 percent / CH2Cl2 / 3 h / -78 - 0 °C
4.1: AlMe3 / tetrahydrofuran; heptane / 0.42 h / 0 °C
5.1: 636 mg / imidazole / dimethylformamide / 3 h / 0 - 20 °C
6.1: 90 percent / tetrahydrofuran / 3 h / 0 °C
7.1: (i-Pr)2NLi / tetrahydrofuran; hexane / 0.25 h / -78 °C
7.2: tetrahydrofuran; hexane / 0.25 h / -78 °C
8.1: 1.05 g / DMAP; pyridine / 0.67 h / 0 °C
With
pyridine; 1H-imidazole; dmap; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide;
In
tetrahydrofuran; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide;
1.1: Alkylation / 2.1: Oxidation / 3.1: Metallation / 3.2: Addition / 4.1: Substitution / 5.1: Substitution / 6.1: Substitution / 7.1: Metallation / 7.2: Addition / 8.1: Acetylation;
DOI:10.1021/jo991642b
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: Bu2BOTf; Et3N / CH2Cl2 / 0.75 h / 0 °C
1.2: 68 percent / CH2Cl2 / 3 h / -78 - 0 °C
2.1: AlMe3 / tetrahydrofuran; heptane / 0.42 h / 0 °C
3.1: 636 mg / imidazole / dimethylformamide / 3 h / 0 - 20 °C
4.1: 90 percent / tetrahydrofuran / 3 h / 0 °C
5.1: (i-Pr)2NLi / tetrahydrofuran; hexane / 0.25 h / -78 °C
5.2: tetrahydrofuran; hexane / 0.25 h / -78 °C
6.1: 1.05 g / DMAP; pyridine / 0.67 h / 0 °C
With
pyridine; 1H-imidazole; dmap; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide;
1.1: Metallation / 1.2: Addition / 2.1: Substitution / 3.1: Substitution / 4.1: Substitution / 5.1: Metallation / 5.2: Addition / 6.1: Acetylation;
DOI:10.1021/jo991642b
