Technology Process of {(2S,3R,5S,6R)-5-Benzyloxy-2-[(6R,7S)-6-benzyloxy-7-(3-benzyloxy-propyl)-7-methyl-4,5,6,7-tetrahydro-oxepin-2-ylmethyl]-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane
There total 23 articles about {(2S,3R,5S,6R)-5-Benzyloxy-2-[(6R,7S)-6-benzyloxy-7-(3-benzyloxy-propyl)-7-methyl-4,5,6,7-tetrahydro-oxepin-2-ylmethyl]-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
((3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane;
With
9-bora-bicyclo[3.3.1]nonane;
In
tetrahydrofuran;
at 20 ℃;
for 4h;
Phosphoric acid (6R,7S)-6-benzyloxy-7-(3-benzyloxy-propyl)-7-methyl-4,5,6,7-tetrahydro-oxepin-2-yl ester diphenyl ester;
With
caesium carbonate;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
In
water; N,N-dimethyl-formamide;
at 50 ℃;
for 16h;
With
sodium hydroxide; dihydrogen peroxide;
In
tetrahydrofuran;
at 0 - 20 ℃;
Further stages.;
DOI:10.1021/ol025814u
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 2-methyl-2-butene; NaH2PO4; NaClO2 / 2-methyl-propan-2-ol; H2O / 1 h / 20 °C
2.1: 3.02 g / trifluoroacetic acid / CH2Cl2 / 0 - 20 °C
3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 2 h / 20 °C
3.2: 62 percent / 4-(dimethylamino)pyridine / toluene / Heating
4.1: potassium hexamethyldisilazanide; hexamethylphosphortriamide / tetrahydrofuran; toluene / 0.5 h / -78 °C
5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C
5.2: Cs2CO3 / PdCl2(dppf)*CH2Cl2 / dimethylformamide; H2O / 16 h / 50 °C
5.3: 86 percent / aq. NAOH; H2O2 / tetrahydrofuran / 0 - 20 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; potassium hexamethylsilazane; triethylamine; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid;
In
tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol;
5.2: Suzuki-Miyaura coupling;
DOI:10.1021/ol025814u
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: KOt-Bu / tetrahydrofuran / 1 h / 20 °C
2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 5 h / 20 °C
3.1: sodium periodate / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 1 h / 20 °C
4.1: 8.39 g / sodium borohydride / methanol / 0.33 h / 0 °C
5.1: 81 percent / iodide; triphenylphosphane; imidazole / benzene / 0.5 h / 20 °C
6.1: 100 percent / KOt-Bu / tetrahydrofuran / 2 h / 0 °C
7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C
7.2: Cs2CO3 / PdCl2(dppf)*CH2Cl2 / dimethylformamide; H2O / 16 h / 50 °C
7.3: 86 percent / aq. NAOH; H2O2 / tetrahydrofuran / 0 - 20 °C
With
1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; potassium tert-butylate; iodide; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine;
In
tetrahydrofuran; methanol; water; tert-butyl alcohol; benzene;
7.2: Suzuki-Miyaura coupling;
DOI:10.1021/ol025814u
