Technology Process of <3α,4β,4aβ,5α(E),6β,8α,8aα>-4-acetamidooctahydro-5-(3-methoxy-1-propenyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,3,8-triol 2,8-diacetate
There total 12 articles about <3α,4β,4aβ,5α(E),6β,8α,8aα>-4-acetamidooctahydro-5-(3-methoxy-1-propenyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,3,8-triol 2,8-diacetate 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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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
- Guidance literature:
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Multi-step reaction with 11 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: 87 percent / 0.5 N aq. HCl / dioxane / 10 h / Ambient temperature
6: pyridine / CH2Cl2 / 31 h
7: 0.5 N aq. HCl / dioxane / 1.5 h
8: Et3N, 4-(dimethylamino)pyridine / 2 h / -40 °C
9: 1.) tetra-N-butylammonium azide, 2.) N-methylmorpholine N-oxide, osmium tetroxide / 1.) CH2Cl2, -40 deg C, 1 h, 2.) THF, 23 h
10: LiAlH4 / tetrahydrofuran / 12 h / Heating
11: pyridine / CH2Cl2 / 6 h / Ambient temperature
With
pyridine; hydrogenchloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; tetrabutylammoniun azide; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; toluene;
DOI:10.1021/jo00380a025
- Guidance literature:
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Multi-step reaction with 10 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: 87 percent / 0.5 N aq. HCl / dioxane / 10 h / Ambient temperature
5: pyridine / CH2Cl2 / 31 h
6: 0.5 N aq. HCl / dioxane / 1.5 h
7: Et3N, 4-(dimethylamino)pyridine / 2 h / -40 °C
8: 1.) tetra-N-butylammonium azide, 2.) N-methylmorpholine N-oxide, osmium tetroxide / 1.) CH2Cl2, -40 deg C, 1 h, 2.) THF, 23 h
9: LiAlH4 / tetrahydrofuran / 12 h / Heating
10: pyridine / CH2Cl2 / 6 h / Ambient temperature
With
pyridine; hydrogenchloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; tetrabutylammoniun azide; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; 1,4-dioxane; 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
- Guidance literature:
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Multi-step reaction with 9 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: 87 percent / 0.5 N aq. HCl / dioxane / 10 h / Ambient temperature
4: pyridine / CH2Cl2 / 31 h
5: 0.5 N aq. HCl / dioxane / 1.5 h
6: Et3N, 4-(dimethylamino)pyridine / 2 h / -40 °C
7: 1.) tetra-N-butylammonium azide, 2.) N-methylmorpholine N-oxide, osmium tetroxide / 1.) CH2Cl2, -40 deg C, 1 h, 2.) THF, 23 h
8: LiAlH4 / tetrahydrofuran / 12 h / Heating
9: pyridine / CH2Cl2 / 6 h / Ambient temperature
With
pyridine; hydrogenchloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; tetrabutylammoniun azide; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane;
DOI:10.1021/jo00380a025
