(2S,4aR,5S,6S,8S,8aS)-6-Benzyloxy-5-((Z)-3-methoxy-propenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromene-2,8-diol

Base Information

• Chemical Name: (2S,4aR,5S,6S,8S,8aS)-6-Benzyloxy-5-((Z)-3-methoxy-propenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromene-2,8-diol
• CAS No.: 106456-20-6
• Molecular Formula: C₂₁H₂₈O₅
• Molecular Weight: 360.45
• Mol file: 106456-20-6.mol

Synonyms:

Chemical Property of (2S,4aR,5S,6S,8S,8aS)-6-Benzyloxy-5-((Z)-3-methoxy-propenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromene-2,8-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4aR,5S,6S,8S,8aS)-6-Benzyloxy-5-((Z)-3-methoxy-propenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromene-2,8-diol

There total 8 articles about (2S,4aR,5S,6S,8S,8aS)-6-Benzyloxy-5-((Z)-3-methoxy-propenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromene-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:

(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 (98903-51-6) → (2S,4aR,5S,6S,8S,8aS)-6-Benzyloxy-5-((Z)-3-methoxy-propenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromene-2,8-diol (106456-20-6)

Guidance literature:

Multi-step reaction with 6 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

With quinoline; hydrogenchloride; 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

Reference yield:

3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1a,3,3a,5,7a,7b-hexahydro-6-methyl-2H-oxireno<1>benzopyran-5-ol (106455-98-5) → (2S,4aR,5S,6S,8S,8aS)-6-Benzyloxy-5-((Z)-3-methoxy-propenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromene-2,8-diol (106456-20-6)

Guidance literature:

Multi-step reaction with 5 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

With quinoline; hydrogenchloride; 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

Reference yield:

(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 (98903-53-8,106499-50-7) → (2S,4aR,5S,6S,8S,8aS)-6-Benzyloxy-5-((Z)-3-methoxy-propenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromene-2,8-diol (106456-20-6)

Guidance literature:

Multi-step reaction with 4 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

With quinoline; hydrogenchloride; 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

upstream raw materials:

<2α,4aβ,5α(Z),6β,8α,8aα>-(1,1-dimethylethyl)<<4a,5,6,7,8,8a-hexahydro-2-methoxy-5-(3-methoxy-1-propenyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-8-yl>oxy>dimethylsilane

(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

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

(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

Downstream raw materials:

(3α,4α,4aβ,5β,6α)-4-acetamido-5,6-(cyclohexylidenedioxy)-3,4,4a,5,6,7-hexahydro-8-hydroxy-3-methylisocoumarin