(1R,2R,3R)-1-(3,4-Dimethoxy-phenyl)-2,3-bis-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ol

Base Information

• Chemical Name: (1R,2R,3R)-1-(3,4-Dimethoxy-phenyl)-2,3-bis-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ol
• CAS No.: 124281-57-8
• Molecular Formula: C₂₂H₂₈O₇
• Molecular Weight: 404.46

Synonyms:(1R,2R,3R)-1-(3,4-Dimethoxy-phenyl)-2,3-bis-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ol

Chemical Property of (1R,2R,3R)-1-(3,4-Dimethoxy-phenyl)-2,3-bis-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ol

Chemical Property:

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Technology Process of (1R,2R,3R)-1-(3,4-Dimethoxy-phenyl)-2,3-bis-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ol

There total 3 articles about (1R,2R,3R)-1-(3,4-Dimethoxy-phenyl)-2,3-bis-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ol 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: 66.0%

gmelinol (469-28-3,597-01-3,17669-45-3,24192-66-3,81495-56-9,96894-16-5,144940-45-4) → (1R,2R,3R)-1-(3,4-Dimethoxy-phenyl)-2,3-bis-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ol (124281-57-8)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 15.5h;

DOI:10.1016/S0040-4020(01)81024-3

Reference yield:

gmelinol (469-28-3,597-01-3,17669-45-3,24192-66-3,81495-56-9,96894-16-5,144940-45-4) → (2S,3R,4R)-4-(3,4-Dimethoxy-benzyl)-3-hydroxymethyl-2-(3-methoxy-phenyl)-tetrahydro-furan-3-ol (124281-58-9) + (1R,2R,3R)-1-(3,4-Dimethoxy-phenyl)-2,3-bis-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ol (124281-57-8)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) RT, 14 h;

DOI:10.1016/S0040-4020(01)81024-3

Reference yield:

(+)-1-hydroxy-6-epipinoresinol 4',4''-di-O-methyl ether (469-28-3) → epidihydroneogmelinol (126906-01-2) + dihydroneogmelinol (172342-93-7) + (1S,2S,3S)-1-(3,4-Dimethoxy-phenyl)-2,3-bis-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ol (124281-57-8)

Guidance literature:

With triethylsilane; aluminium trichloride; Yield given. Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, 0 deg C, 90 min, 2.) CH₂Cl₂, RT, 12 h;

upstream raw materials:

gmelinol

(+)-1-hydroxy-6-epipinoresinol 4',4''-di-O-methyl ether

Downstream raw materials:

[(4aR,10R,10aR)-10-(3,4-Dimethoxy-phenyl)-7,8-dimethoxy-2,2-dimethyl-4,4a,5,10-tetrahydro-naphtho[2,3-d][1,3]dioxin-10a-yl]-methanol

C₂₅H₃₂O₇

C₂₇H₃₄O₈

Acetic acid (1R,2R,3R)-3-acetoxymethyl-1-(3,4-dimethoxy-phenyl)-2-hydroxy-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl ester

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