(aR)-alpha-[(1S)-1-[2,6-Dimethoxy-4-(2-propen-1-yl)phenoxy]ethyl]-4-hydroxy-3-methoxybenzenemethanol

Base Information

• Chemical Name: (aR)-alpha-[(1S)-1-[2,6-Dimethoxy-4-(2-propen-1-yl)phenoxy]ethyl]-4-hydroxy-3-methoxybenzenemethanol
• CAS No.: 171485-39-5
• Molecular Formula: C₂₁H₂₆O₆
• Molecular Weight: 374.434
• Mol file: 171485-39-5.mol

Synonyms:Benzenemethanol,a-[1-[2,6-dimethoxy-4-(2-propenyl)phenoxy]ethyl]-4-hydroxy-3-methoxy-,[S-(R*,S*)]-;Myrislignan;

Chemical Property of (aR)-alpha-[(1S)-1-[2,6-Dimethoxy-4-(2-propen-1-yl)phenoxy]ethyl]-4-hydroxy-3-methoxybenzenemethanol

Chemical Property:

• Boiling Point: 537.6±50.0 °C(Predicted)
• PKA: 9.94±0.31(Predicted)
• PSA: 77.38000
• Density: 1.167 g/cm³
• LogP: 3.64740

Purity/Quality:

98%,99%, ^*data from raw suppliers

Myrislignan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (aR)-alpha-[(1S)-1-[2,6-Dimethoxy-4-(2-propen-1-yl)phenoxy]ethyl]-4-hydroxy-3-methoxybenzenemethanol

There total 24 articles about (aR)-alpha-[(1S)-1-[2,6-Dimethoxy-4-(2-propen-1-yl)phenoxy]ethyl]-4-hydroxy-3-methoxybenzenemethanol 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: 22.0%

C23H30O7 → erythro-Δ8’-4,7-dihydroxy-3,3',5'-trimethoxy-8-O-4'-neolignan (171485-39-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 0 ℃; for 2.5h;

DOI:10.1021/acsmedchemlett.7b00104

Reference yield:

C28H38O8 → (-)?erythro?(7S,8R)?Δ8′?4,7?dihydroxy?3,3',5'-tetramethoxy?8?O?4′?neolignan (171485-39-5)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 8h;

DOI:10.1007/s00706-010-0420-3

Reference yield:

vanillin (121-33-5,8014-42-4) → erythro-Δ8’-4,7-dihydroxy-3,3',5'-trimethoxy-8-O-4'-neolignan (171485-39-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

2.1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

3.1: manganese(IV) oxide / dichloromethane / 72 h / 20 °C

4.1: bromine / chloroform / 24 h / 20 °C

4.2: 72 h / 20 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C

6.1: potassium carbonate / acetone / 18 h / 40 °C

7.1: 15-crown-5; sodium tetrahydroborate / methanol; isopropyl alcohol / 6 h

8.1: hydrogenchloride / tetrahydrofuran; water / 2.5 h / 0 °C

With 1H-imidazole; hydrogenchloride; manganese(IV) oxide; sodium tetrahydroborate; 15-crown-5; bromine; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; 2.1: |Grignard Reaction;

DOI:10.1021/acsmedchemlett.7b00104

upstream raw materials:

threo-(1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-3-O-tosyl-1,2,3-propanetriol

threo-(1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-1-(2,3,4,5-tetrahydropyran-2-yloxy)-2-propanol

4-allyl-2,6-dimethoxyphenol

threo-(1R,2R)-1-[3-methoxy-4-(methoxymethoxy)phenyl]-1-(2,3,4,5-tetrahydropyran-2-yloxy)-2-propanol

Refernces

• 1、 Xia,Wang, Wei. "Asymmetric synthesis of the natural erythro-(1R,2S)-8-O-4′-neolignan myrislignan". . p. 93 - 96. Retrieved 2011/10/01.