Technology Process of (R)-2-[(2S,4S,5S,6S)-6-((3Z,8Z)-(2S,5S,6S,7S)-6-Hydroxy-9-iodo-2-methoxymethoxy-5,7-dimethyl-deca-3,8-dienyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester
There total 25 articles about (R)-2-[(2S,4S,5S,6S)-6-((3Z,8Z)-(2S,5S,6S,7S)-6-Hydroxy-9-iodo-2-methoxymethoxy-5,7-dimethyl-deca-3,8-dienyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester which
guide to synthetic route it.
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synthetic route:
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851889-88-8
(R)-2-[(2S,4S,5S,6S)-6-((3Z,8Z)-(2S,5S,6S,7S)-6-Hydroxy-9-iodo-2-methoxymethoxy-5,7-dimethyl-deca-3,8-dienyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester
- Guidance literature:
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Multi-step reaction with 12 steps
1.1: ozone; pyridine / methanol / -78 °C
1.2: 95 percent / dimethyl sulfide / methanol / -78 - 0 °C
2.1: diisopropylethyl amine / CH2Cl2 / 0.08 h / -78 °C
2.2: Bu2BOTf / CH2Cl2 / 0.75 h / -78 °C
2.3: 76 percent / CH2Cl2 / 1 h / -78 °C
3.1: 95 percent / SmI2 / tetrahydrofuran / 4 h / -10 °C
4.1: KOH / methanol / 20 °C
4.2: 20 percent / silica gel / methanol; hexane
5.1: PPTS / CH2Cl2
6.1: 0.47 g / RuCl2(PPh3)3 / benzene / 8 h / 20 °C
7.1: NaClO2; NaH2PO4*H20; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C
8.1: 0.44 g / benzene; methanol; hexane / 0.25 h
9.1: 83 percent / diisopropylethylamine; DMAP / CH2Cl2 / 8 h / 0 - 20 °C
10.1: H2; quinoline / Pd/CaCO3/Pb / hexane / 8 h / 760 Torr
11.1: 0.397 g / N-iodosuccinimide / acetonitrile; various solvent(s) / 3 h
12.1: TBAF; AcOH / tetrahydrofuran / 36 h / 20 °C
With
pyridine; quinoline; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; tris(triphenylphosphine)ruthenium(II) chloride; samarium diiodide; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; ozone; acetic acid; N-ethyl-N,N-diisopropylamine;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; tert-butyl alcohol; benzene;
3.1: Evans-Tischenko reduction / 10.1: Lindlar reduction / 11.1: Kishi iododesilylation;
DOI:10.1021/ja043168j
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851889-73-1
(2S,3R,4R,7S,10S,11R,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-1,3-[(R)-4-methoxybenzylidenedioxy]-7-hydroxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadec-13-en-8-yn-5-one
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851889-88-8
(R)-2-[(2S,4S,5S,6S)-6-((3Z,8Z)-(2S,5S,6S,7S)-6-Hydroxy-9-iodo-2-methoxymethoxy-5,7-dimethyl-deca-3,8-dienyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: 95 percent / SmI2 / tetrahydrofuran / 4 h / -10 °C
2.1: KOH / methanol / 20 °C
2.2: 20 percent / silica gel / methanol; hexane
3.1: PPTS / CH2Cl2
4.1: 0.47 g / RuCl2(PPh3)3 / benzene / 8 h / 20 °C
5.1: NaClO2; NaH2PO4*H20; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C
6.1: 0.44 g / benzene; methanol; hexane / 0.25 h
7.1: 83 percent / diisopropylethylamine; DMAP / CH2Cl2 / 8 h / 0 - 20 °C
8.1: H2; quinoline / Pd/CaCO3/Pb / hexane / 8 h / 760 Torr
9.1: 0.397 g / N-iodosuccinimide / acetonitrile; various solvent(s) / 3 h
10.1: TBAF; AcOH / tetrahydrofuran / 36 h / 20 °C
With
quinoline; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; tris(triphenylphosphine)ruthenium(II) chloride; samarium diiodide; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; acetic acid; N-ethyl-N,N-diisopropylamine;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; tert-butyl alcohol; benzene;
1.1: Evans-Tischenko reduction / 8.1: Lindlar reduction / 9.1: Kishi iododesilylation;
DOI:10.1021/ja043168j
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851889-75-3
(2S,3R,4R,5S,7S,10S,11R,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-7-isobutyrate-1,3-[(R)-4-methoxybenzylidenedioxy]-5-hydroxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadec-13-en-8-yn
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851889-88-8
(R)-2-[(2S,4S,5S,6S)-6-((3Z,8Z)-(2S,5S,6S,7S)-6-Hydroxy-9-iodo-2-methoxymethoxy-5,7-dimethyl-deca-3,8-dienyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester
- Guidance literature:
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Multi-step reaction with 9 steps
1.1: KOH / methanol / 20 °C
1.2: 20 percent / silica gel / methanol; hexane
2.1: PPTS / CH2Cl2
3.1: 0.47 g / RuCl2(PPh3)3 / benzene / 8 h / 20 °C
4.1: NaClO2; NaH2PO4*H20; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C
5.1: 0.44 g / benzene; methanol; hexane / 0.25 h
6.1: 83 percent / diisopropylethylamine; DMAP / CH2Cl2 / 8 h / 0 - 20 °C
7.1: H2; quinoline / Pd/CaCO3/Pb / hexane / 8 h / 760 Torr
8.1: 0.397 g / N-iodosuccinimide / acetonitrile; various solvent(s) / 3 h
9.1: TBAF; AcOH / tetrahydrofuran / 36 h / 20 °C
With
quinoline; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; tris(triphenylphosphine)ruthenium(II) chloride; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; acetic acid; N-ethyl-N,N-diisopropylamine;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; tert-butyl alcohol; benzene;
7.1: Lindlar reduction / 8.1: Kishi iododesilylation;
DOI:10.1021/ja043168j