Hydroxymatairesinol

Base Information

• Chemical Name: Hydroxymatairesinol
• CAS No.: 20268-71-7
• Molecular Formula: C20H22 O7
• Molecular Weight: 374.39
• European Community (EC) Number: 694-742-8
• UNII: 6F59EK4QQH
• DSSTox Substance ID: DTXSID70942387
• Nikkaji Number: J1.343.874I
• Wikipedia: Hydroxymatairesinol
• Wikidata: Q15411031
• Metabolomics Workbench ID: 141200
• ChEMBL ID: CHEMBL513565
• Mol file: 20268-71-7.mol

Synonyms:7'-hydroxymatairesinol;7-hydroxymatairesinol;7-hydroxymatairesinol potassium acetate;hydroxymatairesinol

Chemical Property of Hydroxymatairesinol

Chemical Property:

• Melting Point: 126-127 °C
• Boiling Point: 634.2±55.0 °C(Predicted)
• PKA: 9.95±0.31(Predicted)
• PSA: 105.45000
• Density: 1.356±0.06 g/cm3(Predicted)
• 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%min ^*data from raw suppliers

(-)-HYDROXYMATAIRESINOL 95.00% ^*data from reagent 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 Hydroxymatairesinol

There total 11 articles about Hydroxymatairesinol 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: 90.0%

(-)-8-{(tert-butyldimethylsilanyloxy)-[4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl]methyl}-8'-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxybenzyl]dihydrofuran-2-one (689277-83-6) → (7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone (20268-71-7,347359-71-1)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 336h;

DOI:10.1021/ol049878b

Reference yield: 86.0%

(3R,4R)-4-{(S)-[4-(benzyloxy)-3-methoxyphenyl](hydroxy)methyl}-3-(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one → (7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone (20268-71-7,347359-71-1)

Guidance literature:

With palladium on activated carbon; hydrogen; In ethyl acetate; for 16h; under 760.051 Torr; Inert atmosphere;

DOI:10.1002/adsc.201300392

Reference yield: 80.0%

(8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone → (7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone (20268-71-7,347359-71-1)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 - 20 ℃; for 3.5h;

DOI:10.1039/b513303c

upstream raw materials:

(-)-8-{(tert-butyldimethylsilanyloxy)-[4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl]methyl}-8'-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxybenzyl]dihydrofuran-2-one

O-tert-butyldimethylsilylvanillin

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

(+)-4-benzyl-3-(2-{(tert-butyldimethylsilanyloxy)-[4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl]methyl}but-3-enoyl)oxazolidin-2-one

Downstream raw materials:

3,3',4,4',7-pentahydroxylign-9,9'-lactone

C₂₂H₂₄O₈

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

matairesinol

Refernces

• 1、 Fuchs, Michael,Schober, Markus,Orthaber, Andreas,Faber, Kurt. "Asymmetric synthesis of β-substituted α-methylenebutyro-lactones via trip-catalyzed allylation: Mechanistic studies and application to the synthesis of (S)-(-)-hydroxymatairesinol". supporting information. p. 2499 - 2505. Retrieved 2013/10/21.
• 2、 Fischer, Joshua,Reynolds, Aaron J.,Sharp, Lisa A.,Sherburn, Michael S.. "Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products". . p. 1345 - 1348. Retrieved 2007/10/03.