Technology Process of (2R,4S,5R,6R)-2-{(S)-(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}-2-methoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-pyran-4-ol
There total 23 articles about (2R,4S,5R,6R)-2-{(S)-(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}-2-methoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-pyran-4-ol which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
Multi-step reaction with 12 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
6.1: 100 percent / HF-pyridine / tetrahydrofuran / 1.25 h / -20 - 0 °C
7.1: 78 percent / Et2BOMe; NaBH4 / tetrahydrofuran; methanol / 1 h / -78 °C
8.1: 50 percent / imidazole / dimethylformamide / 3 h / 20 °C
9.1: DIBAL-H / CH2Cl2 / 0.17 h / -78 °C
10.1: 231 mg / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
11.1: HF-pyridine / tetrahydrofuran / 0.5 h / 0 °C
12.1: 71 mg / p-TsOH / 2 h / 20 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; diethyl methoxy borane; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
1.1: Substitution / 2.1: Reduction / 3.1: Oxidation / 4.1: Metallation / 4.2: Addition / 5.1: Acetylation / 6.1: desilylation / 7.1: Reduction / 8.1: Substitution / 9.1: Deacetylation / 10.1: Oxidation / 11.1: desilylation / 12.1: Cyclization;
DOI:10.1021/jo991642b
- Guidance literature:
-
Multi-step reaction with 15 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
9.1: 100 percent / HF-pyridine / tetrahydrofuran / 1.25 h / -20 - 0 °C
10.1: 78 percent / Et2BOMe; NaBH4 / tetrahydrofuran; methanol / 1 h / -78 °C
11.1: 50 percent / imidazole / dimethylformamide / 3 h / 20 °C
12.1: DIBAL-H / CH2Cl2 / 0.17 h / -78 °C
13.1: 231 mg / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
14.1: HF-pyridine / tetrahydrofuran / 0.5 h / 0 °C
15.1: 71 mg / p-TsOH / 2 h / 20 °C
With
pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; diethyl methoxy borane; trimethylaluminum; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; 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 / 9.1: desilylation / 10.1: Reduction / 11.1: Substitution / 12.1: Deacetylation / 13.1: Oxidation / 14.1: desilylation / 15.1: Cyclization;
DOI:10.1021/jo991642b
- Guidance literature:
-
Multi-step reaction with 14 steps
1.1: 82 percent / PCC / CH2Cl2 / 3 h / 20 °C
2.1: Bu2BOTf; Et3N / CH2Cl2 / 0.75 h / 0 °C
2.2: 68 percent / CH2Cl2 / 3 h / -78 - 0 °C
3.1: AlMe3 / tetrahydrofuran; heptane / 0.42 h / 0 °C
4.1: 636 mg / imidazole / dimethylformamide / 3 h / 0 - 20 °C
5.1: 90 percent / tetrahydrofuran / 3 h / 0 °C
6.1: (i-Pr)2NLi / tetrahydrofuran; hexane / 0.25 h / -78 °C
6.2: tetrahydrofuran; hexane / 0.25 h / -78 °C
7.1: 1.05 g / DMAP; pyridine / 0.67 h / 0 °C
8.1: 100 percent / HF-pyridine / tetrahydrofuran / 1.25 h / -20 - 0 °C
9.1: 78 percent / Et2BOMe; NaBH4 / tetrahydrofuran; methanol / 1 h / -78 °C
10.1: 50 percent / imidazole / dimethylformamide / 3 h / 20 °C
11.1: DIBAL-H / CH2Cl2 / 0.17 h / -78 °C
12.1: 231 mg / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
13.1: HF-pyridine / tetrahydrofuran / 0.5 h / 0 °C
14.1: 71 mg / p-TsOH / 2 h / 20 °C
With
pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; diethyl methoxy borane; trimethylaluminum; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide;
1.1: Oxidation / 2.1: Metallation / 2.2: Addition / 3.1: Substitution / 4.1: Substitution / 5.1: Substitution / 6.1: Metallation / 6.2: Addition / 7.1: Acetylation / 8.1: desilylation / 9.1: Reduction / 10.1: Substitution / 11.1: Deacetylation / 12.1: Oxidation / 13.1: desilylation / 14.1: Cyclization;
DOI:10.1021/jo991642b
