Technology Process of (1R,2S,2'S,2''E,3S,4R,4''E,6S,6''E,8''R,10''S,12''E,14''R)-4-acetoxy-2,3-epoxy-6-hydroxy-1-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexan-1-ol
There total 14 articles about (1R,2S,2'S,2''E,3S,4R,4''E,6S,6''E,8''R,10''S,12''E,14''R)-4-acetoxy-2,3-epoxy-6-hydroxy-1-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexan-1-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:
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942618-52-2
(1R,2S,2'S,2''E,3S,4R,4''E,6S,6''E,8''R,10''S,12''E,14''R)-4-acetoxy-2,3-epoxy-6-hydroxy-1-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexan-1-ol
- Guidance literature:
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Multi-step reaction with 9 steps
1: 95 percent / NaBH4; CeCl3*7H2O / propan-2-ol; tetrahydrofuran / 0.67 h / 0 °C
2: 99 percent / mCPBA / CH2Cl2 / 24 h / 20 °C
3: 99 percent / pyridine; DMAP / CH2Cl2 / 24 h / 0 - 20 °C
4: 94 percent / NaBH4 / ethanol / 9 h / 0 °C
5: 94 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C
6: 83 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
7: 84 percent / mCPBA / CH2Cl2 / 70 h / 0 °C
8: H2; AcOH / Pd(OH)2/C / methanol / 0.5 h / 20 °C / 760.05 Torr
9: 40.2 mg / EDCI; diisopropylethylamine / dimethylformamide / 12 h / 0 - 20 °C
With
pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid;
palladium dihydroxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo070337k
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942618-52-2
(1R,2S,2'S,2''E,3S,4R,4''E,6S,6''E,8''R,10''S,12''E,14''R)-4-acetoxy-2,3-epoxy-6-hydroxy-1-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexan-1-ol
- Guidance literature:
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Multi-step reaction with 6 steps
1: 94 percent / NaBH4 / ethanol / 9 h / 0 °C
2: 94 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C
3: 83 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
4: 84 percent / mCPBA / CH2Cl2 / 70 h / 0 °C
5: H2; AcOH / Pd(OH)2/C / methanol / 0.5 h / 20 °C / 760.05 Torr
6: 40.2 mg / EDCI; diisopropylethylamine / dimethylformamide / 12 h / 0 - 20 °C
With
2,6-dimethylpyridine; sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid;
palladium dihydroxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo070337k
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-
942618-52-2
(1R,2S,2'S,2''E,3S,4R,4''E,6S,6''E,8''R,10''S,12''E,14''R)-4-acetoxy-2,3-epoxy-6-hydroxy-1-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexan-1-ol
- Guidance literature:
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Multi-step reaction with 3 steps
1: 84 percent / mCPBA / CH2Cl2 / 70 h / 0 °C
2: H2; AcOH / Pd(OH)2/C / methanol / 0.5 h / 20 °C / 760.05 Torr
3: 40.2 mg / EDCI; diisopropylethylamine / dimethylformamide / 12 h / 0 - 20 °C
With
hydrogen; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid;
palladium dihydroxide;
In
methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo070337k