Technology Process of tert-butyl (2S,3S,5R)-9-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylnonanoate
There total 7 articles about tert-butyl (2S,3S,5R)-9-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylnonanoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
tert-butyl (3S,5R)-9-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-nonanoate;
With
lithium diisopropyl amide;
In
tetrahydrofuran;
at -40 - -15 ℃;
for 2h;
Molecular sieve;
Inert atmosphere;
methyl iodide;
With
N,N,N,N,N,N-hexamethylphosphoric triamide;
In
tetrahydrofuran;
at -40 - -10 ℃;
optical yield given as %de;
diastereoselective reaction;
Inert atmosphere;
DOI:10.1021/ol801493w
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 74 percent / LDA / tetrahydrofuran / 2 h / -78 °C
2: 86 percent / (R)-MeO-BIPHEP; RuCl3; H2 / ethanol / 25 h / 80 °C / 7500.6 Torr
3: 98 percent / NEt3; 4-DMAP / CH2Cl2 / 20 h / 20 °C
4: 82 percent / CSA / CH2Cl2 / 20 °C
5: 91 percent / LDA / tetrahydrofuran / 5 h / -65 - -30 °C
6: 80 percent / H2 / (S)-(MeO-BIPHEP)RuBr3 / 2-methyl-propan-2-ol; CH2Cl2 / 68 h / 50 °C / 75006 Torr
7: 74 percent / LDA; HMPA / tetrahydrofuran / 3.5 h / -55 - 20 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; ruthenium trichloride; hydrogen; (R)-(6,6′-dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine); triethylamine; lithium diisopropyl amide;
camphor-10-sulfonic acid; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine);
In
tetrahydrofuran; ethanol; dichloromethane; tert-butyl alcohol;
DOI:10.1016/S0040-4039(03)00110-2
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 86 percent / (R)-MeO-BIPHEP; RuCl3; H2 / ethanol / 25 h / 80 °C / 7500.6 Torr
2: 98 percent / NEt3; 4-DMAP / CH2Cl2 / 20 h / 20 °C
3: 82 percent / CSA / CH2Cl2 / 20 °C
4: 91 percent / LDA / tetrahydrofuran / 5 h / -65 - -30 °C
5: 80 percent / H2 / (S)-(MeO-BIPHEP)RuBr3 / 2-methyl-propan-2-ol; CH2Cl2 / 68 h / 50 °C / 75006 Torr
6: 74 percent / LDA; HMPA / tetrahydrofuran / 3.5 h / -55 - 20 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; ruthenium trichloride; hydrogen; (R)-(6,6′-dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine); triethylamine; lithium diisopropyl amide;
camphor-10-sulfonic acid; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine);
In
tetrahydrofuran; ethanol; dichloromethane; tert-butyl alcohol;
DOI:10.1016/S0040-4039(03)00110-2
