(2R,6α,6aα,12aα)-1,2,6,6a,12,12a-Hexahydro-2α-[1-(hydroxymethyl)ethenyl]-8,9-dimethoxy[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6,6a-diol

Base Information

• Chemical Name: (2R,6α,6aα,12aα)-1,2,6,6a,12,12a-Hexahydro-2α-[1-(hydroxymethyl)ethenyl]-8,9-dimethoxy[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6,6a-diol
• CAS No.: 97673-80-8
• Molecular Formula: C₂₃H₂₄O₈
• Molecular Weight: 428.439
• Mol file: 97673-80-8.mol

Synonyms:(2R,6α,6aα,12aα)-1,2,6,6a,12,12a-Hexahydro-2α-[1-(hydroxymethyl)ethenyl]-8,9-dimethoxy[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6,6a-diol;12-Dihydrodalbinol

Chemical Property of (2R,6α,6aα,12aα)-1,2,6,6a,12,12a-Hexahydro-2α-[1-(hydroxymethyl)ethenyl]-8,9-dimethoxy[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6,6a-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6α,6aα,12aα)-1,2,6,6a,12,12a-Hexahydro-2α-[1-(hydroxymethyl)ethenyl]-8,9-dimethoxy[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6,6a-diol

There total 3 articles about (2R,6α,6aα,12aα)-1,2,6,6a,12,12a-Hexahydro-2α-[1-(hydroxymethyl)ethenyl]-8,9-dimethoxy[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6,6a-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: 82.0%

dalbinol (41993-79-7) → 12α-dihydroalbinol (97673-80-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jnatprod.9b01224

Reference yield:

rotenone (83-79-4) → 12α-dihydroalbinol (97673-80-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium dichromate; acetic acid / water / 18.5 h / 20 - 60 °C

2.1: N-phenylselanylphthalimide; (1S)-10-camphorsulfonic acid; water / dichloromethane / 72 h / 20 °C / Inert atmosphere; Darkness

2.2: 6.5 h / 0 - 20 °C

3.1: sodium tetrahydroborate / methanol / 2 h / 20 °C / Inert atmosphere

With potassium dichromate; sodium tetrahydroborate; N-phenylselanylphthalimide; (1S)-10-camphorsulfonic acid; water; acetic acid; In methanol; dichloromethane; water;

DOI:10.1021/acs.jnatprod.9b01224

Reference yield:

12a-hydroxyrotenone (509-96-6) → 12α-dihydroalbinol (97673-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-phenylselanylphthalimide; (1S)-10-camphorsulfonic acid; water / dichloromethane / 72 h / 20 °C / Inert atmosphere; Darkness

1.2: 6.5 h / 0 - 20 °C

2.1: sodium tetrahydroborate / methanol / 2 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; N-phenylselanylphthalimide; (1S)-10-camphorsulfonic acid; water; In methanol; dichloromethane;

DOI:10.1021/acs.jnatprod.9b01224

upstream raw materials:

dalbinol

rotenone

12a-hydroxyrotenone

Refernces

• 1、 Russell, David A.,Bridges, Hannah R.,Serreli, Riccardo,Kidd, Sarah L.,Mateu, Natalia,Osberger, Thomas J.,Sore, Hannah F.,Hirst, Judy,Spring, David R.. "Hydroxylated Rotenoids Selectively Inhibit the Proliferation of Prostate Cancer Cells". . p. 1829 - 1845. Retrieved 2020/06/05.