124988-59-6

Basic information

• Product Name: (3S,4S)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one
• Synonyms: (3S,4S)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one
• CAS NO: 124988-59-6
• Molecular Weight: 538.64
• Mol File: 124988-59-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3S,4S)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one(124988-59-6)
• EPA Substance Registry System: (3S,4S)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one(124988-59-6)

Safety Data

• Hazardous Substances Data: 124988-59-6(Hazardous Substances Data)

Upstream product

• 72724-00-6 1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene 
• 124988-58-5 (S)-4-<<4-(benzyloxy)-3-methoxyphenyl>methyl>dihydro-2(3H)-furanone 
• 116185-13-8 (3S,4S)-3,4-Bis-(4-benzyloxy-3-methoxy-benzyl)-dihydro-furan-2,5-dione 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 116185-11-6 benzyl 3-[4-(benzyloxy)-3-methoxyphenyl]propanoate 
• 121-33-5 vanillin 
• 100-39-0 benzyl bromide 
• 30034-49-2 β-(4-benzyloxy-3-methoxyphenyl)propionic acid 
• 33693-48-0 4-benzyloxy-3-methoxybenzyl alcohol 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 1321545-36-1 (R)-2-(4-benzyloxy-3-methoxybenzyl)pent-4-en-1-ol 
• 1321545-31-6 (R)-4-benzyl-3-[(R)-2-(4-benzyloxy-3-methoxybenzyl)pent-4-enoyl]oxazolidin-2-one 
• 1321545-30-5 (R)-4-benzyl-3-[3-(4-benzyloxy-3-methoxyphenyl)propanoyl]oxazolidin-2-one 

Downstream Products

• 145265-02-7 (-)-secoisolariciresinol 
• 148409-36-3 (2S,3S)-2α-(4''-hydroxy-3''-methoxybenzyl)-3β-(4'-hydroxy-3'-methoxybenzyl)-γ-butyrolactone 
• 580-72-3 (2RS,3RS)-2,3-bis-(4-hydroxy-3-methoxybenzyl)butyrolactone 
• 34444-37-6 wikstromol 
• 34444-37-6 epiwikstromol 
• 33464-73-2 3,4-bis<(3,4-dimethoxyphenyl)methyl>dihydro-3-hydroxy-2(3H)-furanone 
• 33464-73-2 3,4-bis<(3,4-dimethoxyphenyl)methyl>dihydro-3-hydroxy-2(3H)-furanone 
• 116185-15-0 dihydro-3-hydroxy-3,4-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-2,(3H)-furanone 
• 124988-62-1 (-)-8-epinortrachelogenin 
• 61521-74-2 (3R,4R)-dihydro-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone 
• 124988-61-0 (+)-dibenzylepinortrachelogenine 
• 124988-60-9 (+)-O-dibenzylnortrachelogenine 

Relevant articles and documents

An access to chiral β-benzyl-γ-butyrolactones and its application to the synthesis of enantiopure (+)-secoisolariciresinol, (-)-secoisolariciresinol, and (-)-enterolactone

Both enantiomers of secoisolariciresinol and enantiopure (-)-enterolactone were synthesized through a highly stereoselective convergent synthesis. An Evans diastereoselective alkylation followed by a substrate-induced diastereoselective -alkylation of the newly formed optically active β-benzyl-γ- butyrolactone gave the β-β′ linkage of the target skeleton. The (S,S)- and (R,R)-enantiomers of secoisolariciresinol and (-)-enterolactone were obtained in 12-14% (11 steps) and 20% (7 steps) overall yield, respectively. Georg Thieme Verlag Stuttgart New York.

A novel approach towards dibenzylbutyrolactone lignans involving heck and radical reactions: Application to (±)-matairesinol synthesis

A highly regio- and stereoselective Heck reaction of iodoarenes with vinylated malonates, generated in situ by fluoride-induced protiodesilylation of alkenylsilanols/disiloxanes to give functionalized styrenes and 1,4-diaryl-1-butenes has been developed. The dibenzylbutyrolactone lignan skeletons have been achieved from 1,4-diaryl-1-butenes by two routes involving diastereoselective radical cyclization as the key step. This strategy has successfully been applied in the synthesis of (±)-matairesinol. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

TOTAL SYNTHESES OF (-)-TRACHELOGENIN, (-)-NORTRACHELOGENIN AND (+)-WIKSTROMOL

The title compounds were obtained by α-hydroxylation of the corresponding α,β-dibenzyl-γ-butyrolactones (lignans of synthetic origin), and were correlated to (+/-)-methyltrachelogenin 9 whose relative structure was definitely established by X-ray cristallography. (-)-Trachelogenin 1 and (-)-nortrachelogenin 12 thus have the (8S,8'S) absolute configuration, whereas (+)-nortrachelogenin 20 (or wikstromol) has the (8R,8'R) absolute configuration.