Technology Process of {(1R,3S,5R,6S,7S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6,7-dihydroxy-8,8-dimethyl-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester
There total 7 articles about {(1R,3S,5R,6S,7S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6,7-dihydroxy-8,8-dimethyl-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
osmium(VIII) oxide; 4-methylmorpholine N-oxide; citric acid;
In
water; tert-butyl alcohol;
at 20 ℃;
for 8h;
DOI:10.1021/ol0483044
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 72 percent / i-Pr2NEt / acetonitrile; methanol; hexane / 24 h / 20 °C
2.1: 87 percent / camphorsulfonic acid / benzene / 1 h / Heating
3.1: 93 percent / (PCy3)2Cl2Ru=CHPh / CH2Cl2 / 11 h / 20 °C
4.1: 2-methyl-2-butene; BH3 / tetrahydrofuran / 3 h / 0 °C
4.2: 91 percent / NaBO3*4H2O / tetrahydrofuran; H2O / 1 h / 20 °C
5.1: 99 percent / imidazole / dimethylformamide / 2 h / 20 °C
6.1: 97 percent / citric acid monohydrate; OsO4; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H2O / 8 h / 20 °C
With
1H-imidazole; osmium(VIII) oxide; 2-methyl-but-2-ene; camphor-10-sulfonic acid; borane; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; citric acid;
Grubbs catalyst first generation;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;
6.1: Sharpless dihydroxylation;
DOI:10.1021/ol0483044
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 87 percent / camphorsulfonic acid / benzene / 1 h / Heating
2.1: 93 percent / (PCy3)2Cl2Ru=CHPh / CH2Cl2 / 11 h / 20 °C
3.1: 2-methyl-2-butene; BH3 / tetrahydrofuran / 3 h / 0 °C
3.2: 91 percent / NaBO3*4H2O / tetrahydrofuran; H2O / 1 h / 20 °C
4.1: 99 percent / imidazole / dimethylformamide / 2 h / 20 °C
5.1: 97 percent / citric acid monohydrate; OsO4; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H2O / 8 h / 20 °C
With
1H-imidazole; osmium(VIII) oxide; 2-methyl-but-2-ene; camphor-10-sulfonic acid; borane; 4-methylmorpholine N-oxide; citric acid;
Grubbs catalyst first generation;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
5.1: Sharpless dihydroxylation;
DOI:10.1021/ol0483044