Technology Process of Acetic acid (4aR,5S,6S,8S,8aS)-6-benzyloxy-2-hydroxy-5-((Z)-3-methoxy-propenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromen-8-yl ester
There total 12 articles about Acetic acid (4aR,5S,6S,8S,8aS)-6-benzyloxy-2-hydroxy-5-((Z)-3-methoxy-propenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromen-8-yl ester which
guide to synthetic route it.
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synthetic route:
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98903-51-6
(1aα,3α,3aα,7aβ,7bα)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1a,2,3,3a,7a,7b-hexahydro-6-methyl-5H-oxireno<1>benzopyran-5-one
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98903-54-9
<4aβ,5α(Z),6β,8α,8aα>-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propenyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol 8-acetate
- Guidance literature:
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Multi-step reaction with 8 steps
1: 86 percent / diisobutylaluminum hydride / toluene; hexane / 2.5 h / -78 - -40 °C
2: 85 percent / BF3*OEt2 / 6 h / -20 °C
3: boron trifluoride etherate / hexane; tetrahydrofuran / 3 h / -78 °C
4: 1.) NaH, tetra-n-butylammonium iodide / 1.) THF, 2.) RT, 21 h
5: 90 percent / H2, quinoline / Lindlar's cat. / CH2Cl2; methanol / 6 h
6: 0.5 N aq. HCl / dioxane / 10 h / Ambient temperature
7: pyridine, dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature
8: 0.25 N aq. HCl / dioxane / 1 h / Ambient temperature
With
pyridine; quinoline; hydrogenchloride; dmap; boron trifluoride diethyl etherate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride;
Lindlar's catalyst;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; toluene;
DOI:10.1021/jo00380a025
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98903-54-9
<4aβ,5α(Z),6β,8α,8aα>-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propenyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol 8-acetate
- Guidance literature:
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Multi-step reaction with 7 steps
1: 85 percent / BF3*OEt2 / 6 h / -20 °C
2: boron trifluoride etherate / hexane; tetrahydrofuran / 3 h / -78 °C
3: 1.) NaH, tetra-n-butylammonium iodide / 1.) THF, 2.) RT, 21 h
4: 90 percent / H2, quinoline / Lindlar's cat. / CH2Cl2; methanol / 6 h
5: 0.5 N aq. HCl / dioxane / 10 h / Ambient temperature
6: pyridine, dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature
7: 0.25 N aq. HCl / dioxane / 1 h / Ambient temperature
With
pyridine; quinoline; hydrogenchloride; dmap; boron trifluoride diethyl etherate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride;
Lindlar's catalyst;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane;
DOI:10.1021/jo00380a025
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98903-53-8,106499-50-7
(1aα,3α,3aα,5α,7aβ,7bα)-(1,1-dimethylethyl)-<<1a,3,3a,5,7a,7b-hexahydro-5-methoxy-6-methyl-2H-oxireno<1>benzopyran-3-yl>oxy>dimethylsilane
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98903-54-9
<4aβ,5α(Z),6β,8α,8aα>-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propenyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol 8-acetate
- Guidance literature:
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Multi-step reaction with 6 steps
1: boron trifluoride etherate / hexane; tetrahydrofuran / 3 h / -78 °C
2: 1.) NaH, tetra-n-butylammonium iodide / 1.) THF, 2.) RT, 21 h
3: 90 percent / H2, quinoline / Lindlar's cat. / CH2Cl2; methanol / 6 h
4: 0.5 N aq. HCl / dioxane / 10 h / Ambient temperature
5: pyridine, dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature
6: 0.25 N aq. HCl / dioxane / 1 h / Ambient temperature
With
pyridine; quinoline; hydrogenchloride; dmap; boron trifluoride diethyl etherate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride;
Lindlar's catalyst;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane;
DOI:10.1021/jo00380a025
