5-Allohydroxymatairesinol

Base Information

• Chemical Name: 5-Allohydroxymatairesinol
• CAS No.: 81623-30-5
• Molecular Formula: C20H22O7
• Molecular Weight: 374.39
• UNII: XA8JFZ2SGM
• Nikkaji Number: J607.700E
• Wikidata: Q104398974
• ChEMBL ID: CHEMBL470875
• Mol file: 81623-30-5.mol

Synonyms:XA8JFZ2SGM;5-Allohydroxymatairesinol;7(R)-Hydroxymatairesinol;(-)-Allo-hydroxymatairesinol;7-Hydroxymatairesinol, (7R)-;UNII-XA8JFZ2SGM;81623-30-5;(3R,4R)-Dihydro-4-((R)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl)-3-((4-hydroxy-3-methoxyphenyl)methyl)-2(3H)-furanone;2(3H)-Furanone, dihydro-4-((R)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl)-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R,4R)-;allo-hydroxymatairesinol;CHEMBL470875

Chemical Property of 5-Allohydroxymatairesinol

Chemical Property:

• PSA: 105.45000
• LogP: 2.18030
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 374.13655304
• Heavy Atom Count: 27
• Complexity: 499

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CC2C(COC2=O)C(C3=CC(=C(C=C3)O)OC)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)C[C@@H]2[C@H](COC2=O)[C@H](C3=CC(=C(C=C3)O)OC)O)O

Technology Process of 5-Allohydroxymatairesinol

There total 10 articles about 5-Allohydroxymatairesinol 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: 72.0%

(7'R,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone (689277-85-8) → (-)-(7R,8R,8'R)-4,4',7-trihydroxy-3,3'-dimethoxylidnano-9,9'-lactone (81623-30-5,347359-71-1)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol049878b

Reference yield:

(7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone (20268-71-7,347359-71-1) → (-)-(7R,8R,8'R)-4,4',7-trihydroxy-3,3'-dimethoxylidnano-9,9'-lactone (81623-30-5,347359-71-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / imidazole / dimethylformamide / 4 h / 20 °C

2: triphenylphosphine; diethylazodicarboxylate / benzene / 25 °C

3: 8.3 mg / K₂CO₃ / methanol; H₂O / 0.5 h

4: 72 percent / (n-Bu)4NF; AcOH / tetrahydrofuran / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; benzene; 2: Mitsunobu reaction;

DOI:10.1021/ol049878b

Reference yield:

(7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone (689277-84-7) → (-)-(7R,8R,8'R)-4,4',7-trihydroxy-3,3'-dimethoxylidnano-9,9'-lactone (81623-30-5,347359-71-1)

Guidance literature:

Multi-step reaction with 3 steps

1: triphenylphosphine; diethylazodicarboxylate / benzene / 25 °C

2: 8.3 mg / K₂CO₃ / methanol; H₂O / 0.5 h

3: 72 percent / (n-Bu)4NF; AcOH / tetrahydrofuran / 20 °C

With tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; water; benzene; 1: Mitsunobu reaction;

DOI:10.1021/ol049878b

upstream raw materials:

(7'R,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone

O-tert-butyldimethylsilylvanillin

(7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone

(-)-(2S,5S)-2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-en-1-ol

Downstream raw materials:

matairesinol

7-Oxomatairesinol

5-acetoxymatairesinol dimethyl ether

5-hydroxymatairesinol dimethyl ether

Refernces

• 1、 Simakova, Olga A.,Murzina, Elena V.,Maeki-Arvela, Paeivi,Leino, Anne-Riikka,Campo, Betiana C.,Kordas, Krisztian,Willfoer, Stefan M.,Salmi, Tapio,Murzin, Dmitry Yu.. "Oxidative dehydrogenation of a biomass derived lignan - Hydroxymatairesinol over heterogeneous gold catalysts". experimental part. p. 54 - 64. Retrieved 2011/09/20.