21966-92-7

Basic information

• Product Name: isolariciresinol dimethyl ether
• Synonyms: isolariciresinol dimethyl ether
• CAS NO: 21966-92-7
• Molecular Weight: 388.461
• Mol File: 21966-92-7.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: isolariciresinol dimethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: isolariciresinol dimethyl ether(21966-92-7)
• EPA Substance Registry System: isolariciresinol dimethyl ether(21966-92-7)

Safety Data

• Hazardous Substances Data: 21966-92-7(Hazardous Substances Data)

Upstream product

• 67560-66-1 (1S)-6,7-Dimethoxy-2t,3c-bis-hydroxymethyl-1r-(4-hydroxy-3-methoxy-phenyl)-tetralin 
• 4718-24-5 (-)-(1S,2R,3R)-1-(3',4'-dimethoxyphenyl)-3-(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid lactone 
• 78178-31-1 methyl α-conidendreamate dimethyl ether 
• 78173-81-6 <(dimethoxy-3,4 phenyl)hydroxymethyl>-2 (dimethoxy-3,4 benzyl)-3 butanolide-4 
• 78647-52-6 (+/-)-4-(3,4-dimethoxyphenyl)-3-methoxycarbonylbutanoic acid 
• 108102-77-8 (R)-4-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one 
• 108102-79-0 (R)-(+)-α-(dimethoxy-3,4 benzyl)hemisuccinate de methyle 
• 74861-40-8 (7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 103477-60-7 1-(3,4-dimethoxyphenyl)-3-hydroxy-5,6-dimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide 
• 103477-67-4 6-(3,4-dimethoxybenzyl)veratrldehyde ethylene glycol acetal 
• 103477-59-4 6-(3,4-dimethoxybenzyl)veratraldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 103477-58-3 2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane 

Downstream Products

• 521-54-0 (7S,8S,8'R)-3,4,3',4'-tetramethoxy-7,6',8,8'-neolignan (-)-galbulin 
• 321747-14-2 tert-Butyl-[(1S,9R,12R)-1-(3,4-dimethoxy-phenyl)-4,5-dimethoxy-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-ylmethoxy]-dimethyl-silane 
• 321747-13-1 Acetic acid (1S,9R,12R)-1-(3,4-dimethoxy-phenyl)-4,5-dimethoxy-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-ylmethyl ester 
• 321747-12-0 dimethyl-4-iso-α-conidendrol 
• 321747-11-9 [(1S,9R,12R)-1-(3,4-Dimethoxy-phenyl)-4,5-dimethoxy-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-yl]-methanol 
• 7249-36-7 2-(3,4-Dimethoxy-benzoyl)-4,5-dimethoxy-benzoic acid 
• 59527-55-8 ditosylisolariciresinol dimethyl ether 
• 78178-23-1 dimesylisolariciresinol dimethyl ether 
• 71772-18-4 α-conidendrin dimethyl ether 
• 26194-59-2 anhydroisolariciresinol dimethyl ether 
• 78178-28-6 α-conidendreic acid dimethyl ether 

Relevant articles and documents

STRUCTURE OF (+)-ISOOLIVIL ((+)-CYCLOOLIVIL) AND SOME LIGNANS.

-

Synthesis and applications of diphosphine ligands derived from the lignan hydroxymatairesinol

Highly efficient methods for synthetic modifications of the natural lignan hydroxymatairesinol into chiral diphosphines similar to DIOP were developed. Catalytic activity and induction of enantioselectivity for the prepared phosphines were evaluated in rh

Synthetic experiments in lignans Part XV - Reductive rearrangements of 2,6-diaryl-3,7-dioxabicycloocatne lignans with AlCl3 and (C2H5)3SiH

The mixture of AlCl3 and (C2H5)3SiH has been found to cleave the benzyl ethers of the lignans, gmelinol, paulownin, wodeshiol and eudesmin leading to a tetrahydrofuran, a tetrahdyropyran or an aryltetralin derivative by reductive rearrangement.

Asymmetric Lignan Synthesis: Isolariciresinol Dimethyl Ether

An asymmetric synthesis of the lignan (+)-isolariciresinol dimethyl ether 1 in nine steps and 13percent yield (83percent optical purity) from veratraldehyde is described.Veratraldehyde was converted to 6-(3,4-dimethoxybenzyl)veratraldehyde 3 by bromination, acetal formation, metalation, and coupling to 3,4-dimethoxybenzyl bromide. 3 was irradiated in the presence of SO2 to give the 3-hydroxy-1-aryl-1,3-dihydrobenzothiophene 2,2-dioxide 4, which was converted to the (R)-1-phenylethoxy derivative 5b. 5b on heating with dimethyl fumarate gave a mixture of primarily two diastereomeric cycloadducts 7b and 7b', both of which had the 1,2-trans, 2,3-trans , 3,4-cis stereochemistry.The major adduct 7b was subsequently assigned the stereochemistry 1S,2R,3S,4S.Separation and hydrogenolysis of the major adduct gave the diester 8, 1S,2R,3R, which was reduced with LiAlH4 to give (+)-isolariciresinol dimethyl ether 1.A racemic synthesis was also carried out via the methoxy sulfone 5a and its trans isomer 5a' in 33percent yield.