Technology Process of (2R,3S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3,5-dihydroxy-2-methyl-heptan-1-one
There total 6 articles about (2R,3S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3,5-dihydroxy-2-methyl-heptan-1-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 91 percent / D-(-)-diethyl tartrate; Ti(O-iPr)4; t-BuOOH / 4 Angstroem molecular sieves / CH2Cl2 / -23 °C
2: 90 percent / Red-Al / diethyl ether / -20 °C
3: 95 percent / PPTS / 25 °C
4: 92 percent / Li; liq. NH3 / tetrahydrofuran / 25 °C
5: 81 percent / Dess-Martin reagent / CH2Cl2 / 25 °C
6: 82 percent / n-Bu2BOTf; i-Pr2NEt / CH2Cl2 / -78 - -5 °C
7: 95 percent / Dowex / methanol; H2O / Heating
8: 91 percent / imidazole; 4-DMAP / CH2Cl2 / 25 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; dowex; diethyl (2S,3S)-tartrate; di-n-butylboryl trifluoromethanesulfonate; ammonia; pyridinium p-toluenesulfonate; lithium; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
4 A molecular sieve;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
1: Katsuki-Sharpless asymmetric epoxidation / 5: Dess-Martin oxidation;
DOI:10.1055/s-2003-40856
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 90 percent / Red-Al / diethyl ether / -20 °C
2: 95 percent / PPTS / 25 °C
3: 92 percent / Li; liq. NH3 / tetrahydrofuran / 25 °C
4: 81 percent / Dess-Martin reagent / CH2Cl2 / 25 °C
5: 82 percent / n-Bu2BOTf; i-Pr2NEt / CH2Cl2 / -78 - -5 °C
6: 95 percent / Dowex / methanol; H2O / Heating
7: 91 percent / imidazole; 4-DMAP / CH2Cl2 / 25 °C
With
1H-imidazole; dmap; dowex; di-n-butylboryl trifluoromethanesulfonate; ammonia; pyridinium p-toluenesulfonate; lithium; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
4: Dess-Martin oxidation;
DOI:10.1055/s-2003-40856
