140223-75-2

Basic information

• Product Name: (3R,4R,5R)-3-<(3,4-Dimethoxyphenyl)methyl>-4-<(3,4-dimethoxyphenyl)bis(phenylthio)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone
• Synonyms: (3R,4R,5R)-3-<(3,4-Dimethoxyphenyl)methyl>-4-<(3,4-dimethoxyphenyl)bis(phenylthio)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone
• CAS NO: 140223-75-2
• Molecular Weight: 757.025
• Mol File: 140223-75-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3R,4R,5R)-3-<(3,4-Dimethoxyphenyl)methyl>-4-<(3,4-dimethoxyphenyl)bis(phenylthio)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R,5R)-3-<(3,4-Dimethoxyphenyl)methyl>-4-<(3,4-dimethoxyphenyl)bis(phenylthio)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone(140223-75-2)
• EPA Substance Registry System: (3R,4R,5R)-3-<(3,4-Dimethoxyphenyl)methyl>-4-<(3,4-dimethoxyphenyl)bis(phenylthio)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone(140223-75-2)

Safety Data

• Hazardous Substances Data: 140223-75-2(Hazardous Substances Data)

Upstream product

• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 60354-22-5 4-[Bis(phenylsulfanyl)methyl]-1,2-dimethoxybenzene 
• 112968-75-9 (5R)-(L-menthyloxy)-2(5H)-furanone 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 108-98-5 thiophenol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 77934-87-3 (5R)-menthyloxy-2<5H>-furanone 

Downstream Products

• 25488-59-9 dimethylmatairesinol 
• 58311-18-5 (2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol 
• 140223-76-3 (-)-(3S,4R,5R)-3,4-bis(3',4'-dimethoxybenzyl)-5-(1-menthyloxy)butyrolactone 
• 135588-81-7 (3R,4R,5R)-3,4-Bis-(3,4-dimethoxy-benzyl)-5-(2-isopropyl-5-methyl-cyclohexyloxy)-dihydro-furan-2-one 

Relevant articles and documents

Enantioselective synthesis of natural dibenzylbutyrolactone lignans (-)-enterolactone, (-)-hinokinin, (-)-pluviatolide, (-)-enterodiol, and furofuran lignan (-)-eudesmin via tandem conjugate addition to γ-alkoxybutenolides1,2

A general and efficient method is described for the asymmetric synthesis of a variety of liguans. 5-(Menthyloxy)-2(5H)-furanones 5 proved to be excellent chiral synthons in this respect and could be transformed with complete stereoselectivity into a number of lignans. The addition of lithiated dithianes 7 to enantiomerically pure butenolides 5 was followed by quenching of the resulting lactone enolate anions with a benzylbromide (9) or with an aldehyde (6). This tandem addition quenching procedure gave the diastereomerically pure adducts 11, 26, or 27 in 50-67% yield, with a carbon skeleton as found in most natural lignans. As examples of the wide applicability of this method, the syntheses of the enantiomerically pure natural lignans (-)-hinokinin (23b), (-)-enterolactone (24a), (-)-pluviatolide (24c), and (-)-enterodiol (25) in overall yields of 29-37% from 5a and (-)eudesmin (30) in 16% overall yield from 5b are described.

Asymmetric Syntheses of Lignans of the Dibenzylbutyrolactone, Dibenzylbutanediol, Aryltetralin and Dibenzocyclooctadiene Series

General procedures are outlined for the asymmetric syntheses of ligands of the dibenzylbutyrolactone, dibenzylbutanediol, aryltetralin and dibenzocyclooctadiene series, from tandem addition products derived from 4-mentyloxybutenolide.