(4aβ,5α,6β,8α,8aα)-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propynyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol

Base Information

Chemical Name:(4aβ,5α,6β,8α,8aα)-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propynyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol
CAS No.:106456-12-6
Molecular Formula:C₂₁H₂₆O₅
Molecular Weight:358.434
Hs Code.:

Synonyms:(4aβ,5α,6β,8α,8aα)-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propynyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol

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Chemical Property of (4aβ,5α,6β,8α,8aα)-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propynyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol

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Technology Process of (4aβ,5α,6β,8α,8aα)-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propynyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol

There total 7 articles about (4aβ,5α,6β,8α,8aα)-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propynyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol 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:

Reference yield: 87.0%

: 106456-11-5
(2α,4aβ,5α,6β,8α,8aα)-8-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4a,5,6,7,8,8a-hexahydro-2-methoxy-5-(3-methoxy-1-propynyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran

: 106456-12-6
(4aβ,5α,6β,8α,8aα)-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propynyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol

Guidance literature:: With hydrogenchloride; In 1,4-dioxane; for 10h; Ambient temperature;
DOI:10.1021/jo00380a025

Reference yield:

: 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

: 106456-12-6
(4aβ,5α,6β,8α,8aα)-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propynyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol

Guidance literature:: Multi-step reaction with 5 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

With hydrogenchloride; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; hexane; toluene;
DOI:10.1021/jo00380a025

Reference yield:

: 106455-98-5
3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1a,3,3a,5,7a,7b-hexahydro-6-methyl-2H-oxireno<1>benzopyran-5-ol

: 106456-12-6
(4aβ,5α,6β,8α,8aα)-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propynyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol

Guidance literature:: Multi-step reaction with 4 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

With hydrogenchloride; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; 1,4-dioxane; hexane;
DOI:10.1021/jo00380a025